A Bit Fruity with Matt Bernstein - The End Of Milo Yiannopoulos

Episode Date: September 4, 2026

The homosexual fascist must be savvy, and Milo Yiannopoulos was (at least for a time) among the savviest. But it wasn’t enough. It never is. The flamboyant British provocateur who wormed his way into American politics was never destined for a seat at the winners’ table, because the winners’ table doesn’t even exist. Today, Kat Tenbarge, Matthew Sitman (of the Know Your Enemy podcast) and I chronicle the most dangerous gay demon of the 2010s, the culture that produced him, and the destruction left in his wake. May the leopards feast. Listen to bonus episodes on Patreon! https://www.patreon.com/mattbernstein Thanks to today’s sponsors! Get 15% off a cuter, more sustainable way to clean at https://www.blueland.com/fruity.  Work smarter, not harder, with Factor meals ready in two minutes at https://www.factormeals.com/fruity50off Listen to Matt Sitman on Know Your Enemy. Follow Matt Sitman on Twitter. Follow Kat on Instagram. Follow Kat on Bluesky. Find me on Instagram. Find A Bit Fruity on Instagram. Learn more about your ad choices. Visit megaphone.fm/adchoices

I woke up one day and I looked over. Oh, no, I don't want to do this anymore. Like, hell is real. I don't want to go there. Baby, you're in hell right now. You're in the realest hell you're ever going to experience right this second. I have a very sex-in-the-city intro. I was just like tip-top typing away.

Like, I couldn't help but wonder. Hello, hello. And welcome back to A BitFruity. I'm at Bernstein. I'm so happy that you're here. I'm wearing this sort of. fishnet top today, which... Context appropriate. I was going to say, it's partially because I'm at the beach and just

have a very limited wardrobe, but it also feels very much like something Milo would have worn in the mid-2010s. I agree. I moved to New York City at kind of a weird time. It was the summer of 2017, some months into Donald Trump's first term as president of the United States, and while most of the country was grappling with the realization that much of the country's white working class was willing to elect an openly racist rapist, many in New York were having a community reckoning of their own. While it's true that a vanishingly small number of New Yorkers

supported Donald Trump in 2016, there were some intentionally provocative, countercultural figures who embraced the aesthetics of fascism because they thought contrarianism at any cost was cool. One such figure was an artist and troll named Lucian Wintrich, an openly racist white gay man then in his late 20s. Lucian went viral for a series of photographs called Twinks for Trump,

wherein he had a number of young, slender, mostly naked gay men pose in Trump merch in his East Village apartment. Those photos were displayed at the Republican National Convention. Times have changed. Lucian has since faded into obscurity. You can only survive on a stupid-ass bit like that for so long, especially when the audience you need to support your artwork is in the process of purging queer people from their coalition.

One of Lucian's last big moments was in late 2016, when he curated a pro-Trump art exhibition called hashtag Daddy Will Save Us. Among the pieces on display were paintings of figures like George Washington and Martin Luther King Jr. wearing Trump hats and a single pill with a $20,000 price tag on it by none other than Martin Screlli. But perhaps the most notable piece was a live performance of a British gay man wearing a MAGA hat and smoking a cigarette while bathing in a tub of pig's blood. That man was named Milo Yanopolis. I really just wanted to introduce him in the tub of pig's blood.

That was important to me. It's a fitting image. It's what we call for shadowing. The bloody Milo Yanopolis, as it turned out, would last a lot longer in the culture than Lucian Winrich did. For years, he's been an alternative right firebrand, a blogger, a manager to comment. Kanye West, all while bouncing in and out of the closet so as to placate his fascist colleagues.

But the fun could only go on for so long. Milo Yanopolis was deported by ICE last week, allegedly after his colleague and one-time friend in Islamophobia Laura Lumer had enough of him. Today, we're going to tell the story of Milo Yanopolis, which I could naively call his rise and fall, but the truth is he's risen and fell so many times it's hard to keep track. There are articles from 10 years ago called The Rise and Fall of Milo Yanopolis. Being a homosexual fascist requires an immense savviness and ability to pivot. And Milo might have been one of the savviest, and it still was not enough.

So let's get in to some of the worst gay lore there is. And to do that today, I am so excited to be joined by friend of the show, burgeoning YouTube star herself, Kat Ten Barge. Welcome back. Thank you so much for having me. And new friend of the show, Matthew Sittman, who you may know from the Know Your Enemies podcast. I know we have a big overlap and many of you are probably excited to be hearing from him. Yes.

Yeah, I'm a little offended. This is my first invite, but despite all that overlap you're talking about. But I'm glad you thought, you know, we're talking about this terrible person. Who's the perfect guest? I was one of them. So it's an ambiguous compliment. but I'll take it, I guess. I mean, I needed a gay guy to back me up on this one.

Right. I have been talking to each of you over the last few days since Milo's deportation back to the UK. And perhaps what's more interesting about Milo in the end is what he came to represent more so than what he actually did. But I'd love to hear your top line thoughts about everything that we are about to talk about. It's interesting.

Listeners to know your enemy know I love poetry. And I don't know if you caught a couple days ago, the great Kentucky farmer and writer Wendell Berry died at age 92. And one of the poems of his that I love is titled Enemies. And I'll just read the first line from it to you. He writes, If you are not to become a monster, you must care what they think. If you care what they think, how will you not hate them?

And so become a monster of the opposite kind. And that poem has been ringing in my ears, so to speak, preparing for this because it is a kind of, you know, on the left, my politics are universalists, right, or I strive for them to be that way. And so my top line comment might be something like when I got the news that Milo was deported, you know, believe it or not a lot of friends sent that news story or a Twitter post to me. My first thought was, I do want to resist the Shaden Freud of seeing a terrible person of something terrible happened to him because my politics, there's actually not like an asshole carve out for what I think how I think people deserve to be treated

or there's not even like a wicked homosexual who takes out his shame and pain on vulnerable minorities himself including other queer people there's not even a carve out for that in my politics so I guess I wanted to say that at the start that we will be very critical of Milo I'm sure all of us will be but I don't relish this and in some ways I resent having to talk about him 10 years after Donald Trump was first elected. And it was really the 2016 campaign when I first, you know, I'd probably heard of him. He was in Catholic Media too, which I was formerly an editor of Catholic magazine. So I've known about him for a long time, but it really was 2016 when I paid attention to him the most. And in some ways, it's like 2026, the year of our Lord, 26. And Milo Unopolis,

we're still recording podcast episodes about him. And for good reason, you know, this was a very revealing story in some ways. The person at the heart of it, I kind of hate that he's getting renewed attention. But in this case, I think it's worth it. Matt, I should not have let you gone first. You bought out the poetry. That was really beautiful.

Oh, that was really good. I did really pour it on thick, didn't I? God, where's your poem? I can't follow that. Well, what I will say, I completely agree with you on your point about not relishing it. I think that that is the instinct.

of so many people and understandably so. I think even my first thought when I saw the news was like, well, I hope he suffers. But I think that that is in fact the instinct that the Trump administration itself is channeling too, which is why they are creating so much social media content around this arrest and deportation and why they are enjoying and relishing it so much as well. I will also say my first time really encounter. countering Milo Yanoplas. In December 2016, I was a student at Ohio University and Milo came to our campus and it was a big deal. Protests. Protests. Yes. It was, it was a bad time. Trump had just won. And I was

working at one of our student outlets covering campus politics. So I had sent a reporter to the event to cover it. And what sticks out to me the most about Milo's presentation is that he was like putting up all of the pictures of people who worked in our women's and gender studies department and just like mocking their appearances, their pronouns. It was so grotesque to witness and the feeling of like, oh my gosh, like these people have won the culture was like something I really remember like feeling that like, oh my gosh, like we're in such a bad, bad cultural moment right now. And of course that was true. But I also think that in sort of watching what happened, to Milo on a personal level since then and also seeing the ways that our culture has responded.

And in some cases, gotten better and in some cases gotten worse and then gotten better again. It's a reminder that like that real depth of depravity was not the end, neither of like where we were at as a society and also where even Milo himself was at. Okay, that was gorgeous. So don't sell yourself short. Poetry of its own kind, cat. Thank you. Should we talk about Milo Yanopoulos?

Let's do it. Yeah. Milo Yanopoulos, listeners of this podcast, No, I Give Context, was born in Kent, England on October 18, 1984, two days after my birthday. What I don't know is he a scorpion. He's a Libra. Milo and I are...

One of your many commonalities. Yes. These core traits don't apply to him at all. It says Libras are fair-minded and different. diplomatic. Well, he might be after all this. I get it now. And I wouldn't wish it on anyone. Another similarity I have with Milo is that he is, according to Jewish law, a Jew. Milo's maternal grandmother was Jewish. He started his career out identifying as a gay Jew, same, but also says that he was baptized and raised Roman Catholic, which he continues to practice. You know that

joke on Seinfeld where Tim Watley converts to Judaism, the dentist, but he like formerly was Catholic and Jerry says if he gets Polish citizenship, he'll have total, like, saying offensive jokes of immunity. That's what I just thinking about when you were describing. Well, he, he kind of claims this in some moments and claim this in others. And when it serves as purposes, a theme I'm, I'm sure we'll return to in this conversation. Milo's parents divorced when he was six, and it seems like his father was pretty much gone with the wind. He grew up mostly with his mom. He grew up mostly with his mom who was not accepting of Milo's homosexuality and his stepfather who was physically abusive. Milo, very open about his daddy issues.

Of course, Trump would become his real daddy, as he would proudly boast. And this is one of the things I do like about Trump. People have traditionally... You love about Trump. Daddy. Don't we say alike, Milo. No, I do. I do.

I do. I love him. You love Trump, man. I do love him. Milo, I think you have a keen sense of Trump's appeal because you, you have a keen sense of Trump's appeal because you call him daddy. I do. Milo hates talking about his childhood.

It is one of the few things that seems to genuinely make him uncomfortable. In a 2016 interview, he said, quote, do someone want to give British accent their best shot? I could do it. Yeah, you do it. Everybody has bad. See, it's bad. I can't do it. No, that's good.

Do it. It's good. Everybody has bad shit happened to them. And you either use it to turn yourself into it. See, it's so bad. I can't do it. All right. I thought it was good.

I'm going to try one more time. Everybody has bad shit happen to them, and you either use it to turn yourself into a star or you become a victim, and I don't have time for victims. If you allow the bad things to define your life, you will only ever be a parasite. I sound like Julia Garner doing Anna Delvey.

That's good. I want your take on that quote, though. It's pretty ironic. I think that like so many people on the, right who have built these really bombastic personalities or not so much of this is just like projection like the way that he talks about victimhood is a self-owned as we will like get into more and more throughout this episode and like he this is exactly what happened to him he has become like the parasite and that is how he is defined in the so much of the public consciousness

abuse and the way he handles it will be a theme throughout this episode he repeatedly just always refuses to identify with a victim because he says that if you identify as a victim, like it'll take over your life. But I'm like refusing to identify as a victim in anything ever did take over your life. Yes. Yes. And that's a really common mentality that I think a lot of people who are abused or go through otherwise traumatic experiences have, which is like, if I accept the label of victimhood, then I'm I'm letting them win. and I'm degrading myself. But I think the reality around it is that accepting that you were victimized is not a bad thing.

And in fact, it's one of the only pathways toward processing what actually happened to you and having any sort of positive outcome from that. Yeah. That's interesting, Kat. And I just would add, you know, that quote that was read in that lovely British accent, And it's kind of almost amusing now, not just because of Milo's story and what we'll get into, but like, what is the right now? But just like, all they do is talk about their grievances.

Like, they might not always call themselves victims in a certain way, but it is just the culture of the right. It's just nothing but grievance. There's little else these days, right? Their unfairness of them, the witch hunts, the unfair persecutions, the beer I like. Now there's a trans person selling it to me and like, you know, what does that but grievance and a claim in its own way of victimhood? Over the decade since that quote, he said that like it's only become more kind of ironical and absurd because that is all the right is. It's like they can only really see victimhood where it isn't. That's so spot on cat.

I mean, think about the way now someone like Elon Musk and others on the right talk about the quote, what, suicidal empathy? That's basically just acknowledging someone's been abused or hurt or mistrust. treated in some way, aka, just like basically what they're saying is I object to having to think about someone not me or in my immediate circle or in my political team suffering in any way. I refuse to. So when you, when someone calls themselves a victim, they're asking to be, they're almost saying, can you have a little empathy for me? Can you understand my situation?

And that is the one thing the right absolutely refuses now to do. I mean, the idea that empathy is like poisonous and suicidal to a culture is just, just, just absurd and ridiculous, but that's their one of their mantras these days. And it has eaten Milo from the inside out. From the beginning, in fact, Milo was kicked out of his high school for what he later called absolutely outrageous behavior. And then he was able to attend Wolfson College in Cambridge, but was expelled there too for repeatedly missing class and work assignments. So in the early 2010s, Milo enters the world as a freshly agreed openly gay, flamboyant, angry adult with no credentials or skills to boast of.

And what kind of job caters specifically to such a person? Conservative media, baby. The ultimate welfare state. The ultimate welfare state is conservative media. It's Jobs, Inc. for losers. You know who this reminds me of, and I'm so sorry. I know we're only 20 minutes into the episode, but I just have to say it. he reminds me so much, like this backstory and where he's about to do with his life of Jeffrey Starr.

Oh, Kat. I know. I'm sorry. I know. I think we're having a cultural divide. Matthew, do you know who Jeffrey Starr is? Yes, but only because my boyfriend Max, I know the reference, but I won't be able to add much beyond. I just said.

That's okay. But I don't really know his backstory, actually. I'll send you a link to the event for the podcast. When we're done recording, I'll go down to have dinner with Maxx. and ask him, can you tell me Jeffrey Starr's backstory? I think you should consider what kind of dinner you want to have before you do that. Okay. The only reason why I think it's worth bringing up is that it is not an unusual experience for a young queer person to experience

childhood abuse and then sort of exhibit these behaviors that are very common in people who have been abused, like getting kicked out of school, like disciplinary issues, outbursts, things of that degree and then pivot that into a lot of like anger and bigotry toward the world around them. And you see this in the internet age in the form of like, I think a lot of people's viral careers. 100%. Good parallel. Deborah Messing, you're up next. One of Milo's first jobs was at the conservative British newspaper, The Daily Telegraph, where he wrote a tech column. But his real star began to rise in 2014 when a 28-year-old Milo was picked up by Steve Bannon at his outlet Breitbart News. At just the right time, Steve Bannon

scouted Milo seeing in him his ability to champion online outrage politics. And Breitbart has less than a million monthly readers nowadays and doesn't have nearly the same cultural sway it once did. But in the years leading up to Trump's first election in 2016, Breitbart became the primary outfit of the burgeoning alt-right. And this was in large part because of the work of Milo Unopoulos, who from 2014 to 2017 helped shape Bright Bart's brand, helped shape Bright Bart's brand, help shaped Bright Bart's of white supremacist in neo-Nazi media. Do you think your erstwhile boss, Steve Bannon, chairman of Bright Bart and Trump, now Trump's chief strategist, do you think he has horribly regressive attitudes? He's been described by some liberals and anti-Semite, a white, to white,

nationalists. Have they got that wrong? Well, Breitbart is a company staffed almost entirely by Jews. I am a gay Jew and he made me into a start. This stuff is ridiculous. What a lot of Brits don't always understand is how ugly and terrifying American politics can be. The name-calling can be absolutely extraordinary. And lots of Brits... And name-calling by Breitbart. I mean, that is ugly. Look at these headlines. Would you rather your child had feminism or cancer?

Well, that's not stupid. That's mine. There's no hiring bias against women in tech. They just suck at interviews. interviews. That's extreme. That's how good. No, it's not extreme. They're my headlines. They're not Steve's. Do you guys just want to paint a brief portrait of Breitbart and the mid-2010s alt-right for people who weren't there or need to be transported back there for some reason? Because I think now the alt-right is sort of like a catch-all for anyone who's like on the far right or has like wacky beliefs or something. But it came to be in a specific context. Yeah. It was just like a totally wild. Well, first of, the presidential campaign in 2016 was absolutely wild. Like, remember,

like Trump brought out Bill Clinton's accusers, right? They had a press conference. Then he sat them in the audience, right? While debating Hillary, uh, Hillary passed out on the 9-11, uh, anniversary event and had to be like dragged in the back of a like white van by her handlers. Like it was crazy, crazy things were happening. There was crazy people everywhere, too. But it mattered because Breitbart was, you mentioned it was Steve Bannon that recruited Milo, and then Steve Bannon became Trump's campaign manager. So like reading Breitbart, if you were in, if you cared about politics or you were covering politics, you were following it a certain way, like you kind of had to read Breitbart in a way because it was an insight into Trump's campaign manager's thinking.

And it was very much, like Matt, you mentioned like we say that all right now means X, Y, or Z. But really, like, I think the distinction, like the way, the reason alt-right has fallen out of usage in a certain way and a certain descriptive values is because the all right has won. Like it kind of just is the right now. Yes. Yeah, because think about in 2016, there were all the never Trump conservative intellectuals that, you know, eventually did bend the knee or came on border, at least became very, very anti-Trump. Right. There was Republicans who resist them. Remember, Ted Cruz was booed at the 2016 RNC.

They kind of had trouble filling spots, I think, like Peter Thiel spoke. It was all very odd, but it was because you had the mainstream conservative think tanks, institutions, magazines, intellectuals. You had the mainstream Republicans who were iffy toward Trump, right? Trump took over the Republican Party. But now, like, we don't think of those terms exactly at all, do we? It's kind of like it back when Trump took over the Republican Party, won the primary, and then somehow won the presidency, it was a shock because of people like, like Milo, right, all around him. Like, these were, it was like whoever Trump could get to kind of speak on his behalf in public due events, spread the MAGA message. Like, however, it was a real

island of the misfit toys in 2016. And so that's kind of what I recollect when I think back, it was just like such a carnival. So many things that were like shocking, but now seen, not quaint exactly, but it's almost like, there were these like outside thing that was like, wow, this isn't normal. But now it's just totally, look who the secretary of war. is. Look who's like doing comms for the Trump administration. Look who is being elected to Congress in some cases. Like, Plyle himself has risen and fallen many times, but people like him have kind of triumph in terms of who's running the Republican Party, which is to say running the country right now. Totally, totally agree. I think back, like the alt-right initially came to be, meaning like,

oh, these are Republican identifying people who aren't afraid to say things that are just like brazenly racist or anti-Semitic. And I remember a lot of the objection to him at the time from people like Ted Cruz and Ben Shapiro. I mean, Ben Shapiro has always had a sensitivity towards anti-Semitism or at least anything he perceives as anti-Semitism,

which is funny because he's not to make this about Ben Shapiro, but he's always been very willing to be bigoted towards literally every other group of people, but when it comes to Jewish people, but in a way, I feel like the Republican Party before this 2016 era really fashioned it.

as like high-minded people that like weren't racist, that weren't anti-Semitic, that actually had an aversion to these things. And maybe it was just about tax policy and like being anti-abortion. But I do think that the alt-right and interestingly now MAG is the establishment, but the MAGA party that it gave way to was a more honest look at what these people were doing with their policy and the way that it affected people. I view like this era of Breitbar and sort of like the media project of Breitbart News. They explicitly positioned to themselves as the opposite of the

Huffington Post. I also see them as sort of like the counterforce to like Tumblr, which is where I was as a teenager in the 20, early to mid-2010s, like reading about social justice and like learning about all of these

concepts like feminism. On that side of the internet, there was just so much like progressive discourse happening, like bringing in a lot of young people, especially a lot like women and queer people and associating it a lot of the time with like fandom and like cultural properties that were more diverse and that people were like really leaning on at that time and like sort of coming out of that era Breitbart is doing it but the exact opposite way

I've I've taken some time out of my busy schedule being fabulous and they're doing my hair to prepare a speech for your well a few remarks really feminism is cancer thank you very much And Steve Bannon's sort of ideology around this was like culture is the gateway to bringing people into these political moments that they would otherwise shy away from. Like they were of course extremely Islamophobic. They were of course extremely anti-immigrant and xenophobic. They were of course overtly misogynistic, aligned with white supremacists, aligned with anti-Semitism. But I think that what Breitbart did really, really well is that they got people's attention with more like cultural stories. and more like shocking and salacious stories,

which is exactly the model that you see all of these now. Now the right-wing media ecosystem has splintered in so many different directions, and you have your Candace Owens's and you have your daily wires, which is already kind of itself on the way out. Like you have all of these different people and podcasters, but that style of being like, boom, Hollywood story, boom, you should support banning immigration. like that's what Breitbart did and it did it so well as a backlash to what more progressive places like BuzzFeed and HuffPost and Tumblr were doing.

And a backlash to kind of insufficient baseness in other parts of the right. You know, it's like we're not reading National Review and valorizing Ronald Reagan anymore. Someone like Bannon's like, I'm a Leninist. Claimed like a kind of radical like this was an insurgency, an ideological insurgency, not just a, against wokeness and progressives and kind of like the establishment in that sense, but against the establishment on the right, as I was mentioning earlier. And because Breitbart was founded by Andrew Breitbart. I forget what year he died, but it was, you know, one reason Bannon took over was the founder of Breitbart, like dropped out of a heart attack, like on a sidewalk in L.A., but he was very friendly

with like a lot of mainstream conservatives. People at National Review, they still speak highly of him. And it's almost like if Andrew Breitbart hadn't died, you know, dot, dot, dot, maybe we could have avoided all this. But it was a critique of the existing right, too. Because the existing right was anti-Trump for the most part, especially at the start. And it was the bright, like Bannon had this magazine, this publication that he could, you know, kind of wield as a MAGA weapon. Now, Milo was also openly gay the whole time.

And very much not in a if you know, you know, kind of way like how someone like Douglas Murray remains today. Milo was openly gay in a bombastic, hypersexual way. He would often half-heartedly reject accusations of his own racism by saying to crowds of people that he, quote, loves sucking black dick. Well, I'm not just that. I'm a gay Jew with a black fiancé. So attempting to crown me queen of this white supremacist movement is a bit of a stretch. I think, you know, I...

His 2015 and 2016 speaking tour was called The Dangerous Fagget Tour. Not a bad name. Not a bad name. Catchy. But I mean, what do you guys make of this type of character appealing to the right and in a social and professional circle populated by notorious homophobes? And I don't know. I think there's something here about how the 2010's alt-right,

but certainly not the traditional right, created a space for eccentric figures like this to survive if they were sort of loud and bombastic enough about their racism and sort of finger pointing towards other minorities. But I'm curious for your take. I do think that a lot of people in Milo's audience thought that he was really funny. Because I think a lot of this is like, oh, well, you're, you're owning it, but you're also, like, making fun of it and you're degrading yourself and you're degrading, like, your sexuality and what you do and you're doing it for art.

entertainment while also aligning with our worst and more serious, like, racist impulses. So, therefore, like, we think you're funny and we think you're entertaining and we're going to, like, just kind of support what you're doing without actually supporting anything, of course, meaningful, like, for your community. I don't even think they look at it like that. They just look at it as like, oh, Milo, he's, like, hilarious. And he says stuff that I agree with, like, 75% of the time. That's very good. I mean, Matt, this gets to the, the, the day. Faggot title, right, of his tour. Like, like the self-deprecating or self-insulting, I should really say nature of that, right? It's almost like saying, I don't, like you can laugh

at me. And that makes it okay at some level. But I think it's really the idea that the kind of alt-right, bright part, et cetera kind of spaces made space for these people is true. And it gets back to the island of the misfit toys. It's kind of like you could be black, you could be gay. you could be like a member of some group that the right doesn't like but if you were kind of absurd enough and and kind of almost self-deprecating the way we're describing myelo being like that was fine yeah and it served the purpose of what you know you can say as a gay man right i you kind of vouch for the right always does this right there's women black people gay people right there's always whatever kind of minority any group that the right you think why would someone

Who is this, be so supportive of, or these kinds of politics and policies? Well, I mean, that's very lucrative to be one of those. If you're the X, Y, or Z that the Wright chooses, that's always a lucrative job. There's a lot of money on the right. But I think especially in this 2016 kind of early moment, the Breitbart moment, it really wasn't Island of the Misfit Toys. And in some ways, it was only going to be those kinds of people, right? If you were more sober and kind of normal or mainstream, however you want to describe it.

Yeah. Right. You would not have gotten any traction or attention. And it was partly just the whole absurdity, just kind of like the spectacular nature of it all that was part of the, like we like to say on our podcast, MAGA is the mess. Right. Like think about Trump rallies. All the people, they're like a carnival, almost circus like sometimes even revival like atmosphere. Right.

But it's that sense of chaos, crazy people, stuff's going to happen. I don't know. That's all in the mix. And I feel like someone like Milo, his particular brand, the bombacity and the self-deprecating. nature of it too. I think that's that's very like of the moment and it it's not exactly shocking in some ways when you think about how the right operates in the ways I was just describing. I think people also sometimes forget that Trump won tolerated certain types of gay people like rather openly. Peter Thiel to me that's someone I mentioned a few moments ago. Peter Thiel. I mean Milo spoke at like I

mentioned the 2016 Republican National Conventions Gays for Trump Rally, which is a existed back then. You think there's a gaze for Trump rally in the upcoming 2028 RNC? Absolutely not. I mean, there was still a room for like earnest advocacy for gay people within the Republican party. And many of us back then were saying, well, that's going to go away, though. If you pursue this to its logical endpoint, that's going to go away. And what's interesting is that Milo says in many interviews at the time of the height of his fame, that discrimination against gay people was a thing of the past. Like, he would acknowledge that gay people were discriminated against.

And he said, well, that's over now. I'm going to put in clips here. And it's crazy because it's not. Yeah, but identity politics also comes from understanding people who have been marginalized in the past and did need protection and perhaps still do. In the past, for sure. I think as to whether or not they still do, gayes, I think we're doing fine. Gay people are doing fine.

Matt, I have a question for you. Like, I remember the Twinks for Trump art exhibition gallery showing that you mentioned earlier. But I feel like as a gay guy, like I definitely knew about that. My friends knew about it. Even if they would text me the Lincoln in kind of ironical or joking about it or even critical ways. But I feel like there was a way in which as a PR campaign, it succeeded in some way in breaking through or at least kind of success might not be the right word. But as with all these, it might be self-defeating ultimately, but in terms of just the attention right away, what was your sense of that? So, yes, because Milo spoke at the RNC in front of huge prints of these Twinks for Trump naked boys wearing Trump hat photos, which is just so ridiculous to think about now. My memory of the Twinks for Trump thing was I had just moved to New York. I was 18 years old. I thought that moving to New York city from a suburb in New Jersey was going to be this moment where I'm like, I go to love is love paradise. And it's like all the gay people here are like cool and everyone's amazing and politically sound and everyone like hugs each other good night or something. And urban metropolis is

with a, you know, a big gay population. There is that. There is that. But I remember one of the first things I heard about was this controversy where a bunch of like downtown gays in the art scene had participated in this Twinks for Trump photo shoot. I think I thought then what I still think now, which is just like, what a bunch of losers seeking attention? Like, what a bunch of fucking losers seeking attention? You're not good artists.

The only currency that you have that you can work with is outrage. And what a fleeting way to exist as exemplified by the man we're talking about today? Like, yeah, I don't think it worked in producing any sort of meaningful Republican gay cohort. I just think it like, it's like, there's always this like downtown dirtbag culture in New York that I don't respect that does everything like ironically. And it's like, are we really Trump supporters? Are we just pretending to be Trump supporters and taking sexy photos? Who cares? Get a life. Make better art. Yeah. And the only other thing I want to add to this is I feel like in a certain sense, Matt, for just the reasons you described. But I feel like it kind of all held together too because Trump is kind of

the first gay president. Yes. Dancing to YMCA. Like, there really was a thing where, like, well, Trump, he's not going to be that bad for gay people because he's from New York. He loves Broadway show tunes. He's not, he's not like this visceral homophobic. And do you remember the incredible moment where the gays for Trump, like the homemade gays for Trump when one of the daughters spoke? Yeah, Tiffany, oh my God, Tiffany Trump wasted off her ass. Gave like the keynote speech. So let me just say how excited I am to be here in this room with probably so many of my friends that I see a few of you.

already in here. It's such an honor. I love you. It's truly, it's such an honor to be able to be here and speak truthfully, honestly, and from my heart. I know what my father believes in. Prior to politics, he supported gays, lesbians, the LGBQIA plus community, okay? And people, you unfortunately, you see social media, you see these fabricated lies, it saddens me. I have friends of mine who reach out and they say, how, they make up stories, how would you support your father? We know you, we know your best friends are, yay, we know your best friends are this, this, this. I say it's because my father has always supported all of you. Okay?

He's not doing it for politics and unfortunately, I think there's a lot of people out there and other politicians who do. do. Okay? When my father decided to run as for the Republican nomination, I can say I was, you know, I was a little bit worried just based on previous, you know, the past, the past Republican establishment and how, you know, their views maybe were towards this community, towards gays, lesbians. But guess what? My dad cannot be bought off. He's not going to let anyone change his views and he's done that. And I pray that you all see that. My mom's here in the audience, okay?

She flew down. I mean, some of her best friends when she was on Broadway, like unfortunately, one of her best friends passed away from AIDS. He said, my mom had so many friends in New York who were gay actors who all died of AIDS. Yes. And it was like... And she came on to like upbeat pop music and then she was like, all my mom's friends died of AIDS and everyone was like, oh. Yeah, because I do have a gay sense of humor.

There's something like darkly funny about that, like that particular like statement in that context, but it's darker in a worse way to do. Like it's, it's it's kind of like speaks to that like no matter how far you go with these people. There's they'll always remind you of the dark, dark kind of underbelly. I would like to take a quick break from the show to give a shout out to the sponsor of today's episode Factor. I present as cool, calm, and collected on this show, and I think that that's a pretty good representation of how I am in real life too. However, I also get overwhelmed sometimes by the seemingly never-ending list of obligations that we all have, friend obligations, family obligations, work obligations. obligations, health obligations, and one of the places where I would like to have as few obligations

as possible is in the kitchen. I want food easy, and I want food that tastes good, and that's interesting, and that is where Factor comes in. Factor is a meal delivery service with chef-made gourmet meals that are already to heat and eat in just two minutes. Factor has a rotating menu of over a hundred different meals every single week. So you are never going to have to get into the monotony of meal prepping chicken and rice every day, respect to the people who do it. There are a bunch of different menus that can help attend to your dietary needs and preferences.

If you want to shake up your home food prep routine without putting in really any extra effort at all, but reaping all the benefits of nutrients and delicious meals, you could try factor today and at a discount. Head over to factormeals.com slash fruity 50 off with the code fruity 50 off to get 50% off and one free breakfast item per box for a year while supplies lasts through October 31st, 2026. That is factor meals.com slash fruity 50 off with the code fruity 50 off. This episode is also sponsored by our last. longest running sponsor here at the A Bitfrutty podcast, and that would be Blue Land. I've been using Blue Land in my home for close to three years now, and in fact, when I filmed this very episode that

you're listening to, I was in a beach house that also had Blue Land products, unbeknownst to me upon arriving there, but it felt cosmic. Blue Land makes dish, laundry, and household cleaning products reimagined and designed to eliminate single-use plastic. Chances are, the cleaning stuff you're using right now has a ton of plastic that is ending up in landfills, whether it is plastic bottles or the film that coats your laundry pods. Blue Land is based around a tablet system and all of their tablets are 100% plastic-free. And trusted in over a million homes, including mine and the beach house that I just went to for five days.

With Blue Land, you just buy one forever bottle, pop in a tablet, fill it with water, and you're ready to go with your cleaning solution. And when you run out, you can just pop in another tablet. And those tablets start for as low as $2.25. So not just easier on the planet, also easier on your wallet. If you'd like to try Blue Land, you can get 15% off your first order at blueland.com slash fruity. That is blueland.com slash fruity. And now let's get back to the show.

from Milo's perch at Breitbart News, he became one of the primary aggressors of Gamergate, a massive online harassment event that allowed Milo to ride the wave of the culture war all the way into the heart of the United States. Kat, could you explain what GamerGate was and the precedent that it created for online harassment campaigns? TLDR on GamerGate. So Gamergate established the modern playbook for smear campaigns and harassment. And the phrase GamerGate is Everything has come to describe so much of our culture in particularly like the 2020s. But where it started was it started with this harassment campaign against women in the video

games industry, women game developers, women who made YouTube videos about pop culture. what this came from was it was a backlash against feminism and there were these like lies and there were these smear campaigns built around the idea that female game developers could sleep with men who covered video games as journalists to gain favorable coverage. That's where the phrase like it's about ethics in gaming journalism comes from. But of course this wasn't true. Like of course this was completely rooted in nothing. Like the woman who was targeted in the woman who was targeted in the beginning and the man who she was accused of being in this relationship with for clicks, like there wasn't even any real coverage that was happening. Like they just, they just invented it.

There's a lot. It goes into a lot more detail that we don't really have time for today. What is important about GamerGate is that I think it combined a lot of the key elements of like these types of campaigns, which is like disinformation, online coordination, which at that time was like bright bar and specific online forums, an online. slot that these days is conducted through like algorithm driven social media feeds, which were new and emerging at that time. It's like if you post enough about something, it'll start being put onto every single person's feeds and it creates this like cascading network effect. So that's a big part of what Gamergate was. And Milo and Breitbart were really bolstering and allowing this campaign to get as big as it did by covering it for

bright part. And I mean, I feel like Gamergate set the playbook for like online harassment to drive people out of public life, particularly like minoritized people through doxing, through death threats, through all of that stuff. And the Gamergate playbook has really been almost industrialized by things like Canary Mission, which targets anyone who is pro-Palestinian in public by Libs of TikTok who targets anyone who's LGBT in public in the same place as children. What's interesting is one year prior to Gamergate, Milo mocked gamers as, quote, unemployed saddos living in their parents' basements. But of course, that did not matter if joining their cause positioned him as having the

upper hand against online feminists and social justice warriors and women in general, then that's what he was going to do. From the Guardian, quote, Gamergate's activists and opponents both agreed that without Milo's advocacy, the movement would have fizzled out. I want to tell you guys Milo's core political tenets as I see them. This is how I summarize them. One, Trump is daddy. Two, feminism is cancer.

Even saying those three words, it brings me, it's like a shot of 2016 right into my system. Feminism is cancer. His big thing is like that he would literally say on speaking tours was like, would you rather have a child with cancer or a child who's a feminist? It's classic. Three, feminists and people of color and liberals are society's real oppressors and political correctness is the sword they wield to crush free speech. Four, Islam is bad because it's caused oppression for women and gay people, but Christianity is good despite having done the exact same thing. And also, women and gay people are bad anyway, but it's not racism, I promise.

Five, Muslims are an inherent threat to Western society. Thus, their immigration into the U.S. must be stopped. Okay, these tenets exactly as you have written them, are what Elon Musk fed into the Twitter algorithm to create X as it exists today. Like, to your earlier point, Matt, about how, like, this is just what the whole right is now. Like, this is, if you could distill Elon Musk, the world's richest man who controls so many of our communications platforms, like, this is, this is him now. This is what Elon is now. I want to make one more point that follows from GamerGate specifically. And Matt, it goes to a number of the, you know, distilled, Milo beliefs you mentioned, which is, I kind of think the sequence of the misogyny and anti-feminism at the heart of Gamergate. What years would you say the height of Gamergate would have been?

2014, 2015. Okay. And do you remember, Trump, one way he broke through, the very first Republican debate, remember his attack on Megan Kelly? Mm-hmm. She gets out and she starts asking me all sorts of ridiculous questions. And, you know, you can see there was blood coming out of her eyes, blood coming out of her, wherever. Making those comments going after Rosie O'Donnell. You've called women you don't like fat pigs, dogs, slabs. and disgusting animals. Your Twitter account.

Only Rosie O'Donnell. Very dated reference. Although she's back on TV. Everything old is new again, apparently. But like the misogyny at the heart of the Trump campaign, I think in some ways the Gamergate, the massagy and anti-feminism at the heart of that was a way of like priming the pump for someone like Trump, who very first debate, before we knew his opponent even would be Hillary, right, was talking about,

the debate moderator's menstrual cycles, right? And making fun of Rosie O'Donnell. And it turns out, this is the man who wins the nomination and then defeats the first women candidate for, you know, of a major party. Like I don't, I think that kind of trajectory and linkage is not accidental. Trump was, Trump was riding a wave that was maybe not started by Milo, but that Milo was instrumental in kind of churning up. That's exactly right. And that's why you saw so much of the same Gamergate architecture around Deppie Hurd in 2022, which then paved the pathway for Trump to come back into power, riding the wave of denying, you know, abuse allegations and, and using cultural Darvo on this massive scale. Following the success of Gamergate in not only bullying a number of

women into years-long solitude, but also turning Milo unopoulos into a folk hero of the online right, Milo thought, why stop there? And so, with his celebrity on the rise in 2016, when a Ghostbusters remake was released featuring an all-female cast, which included Leslie Jones, online alt-right wingers levied a misogynistic and racist harassment campaign

against the film and its cast, specifically targeting Leslie Jones for being a black woman. Milo led his hundreds of thousands of followers on Twitter to dog pile on her and posted a barrage of tweets himself, calling her, quote, barely literate, a black caricature, and a black dude. This led to Leslie Jones leaving Twitter, which, of course, the goals of campaigns like this,

which, by the way, are the real cancel culture, might I add, Milo's own account was then suspended by Twitter for violating rules around harassment back when Twitter still had those. L-O-L-O-L-L. Throughout 2016 and 2017, Milo spouted his beliefs in the most incendiary possible way at anyone who would give him a microphone and accused anyone who did not give him a microphone

of being insufficiently devoted to the cause of free speech. If you don't let me speak on your campus and give me money, you are against free speech. It's so fucking ridiculous. I think it's relevant to discuss here something that I feel very passionately about, which is that Milo's fame was not inevitable, but in my opinion,

manufactured by a media apparatus that simultaneously treated him like a mean gay joke and like a serious person who represented free speech itself. Similar to other previously obscure figures like Barry Weiss or Dasha Necrosova in the later 2010s, working on a bonus episode about Dasha right now,

subscribe to the person. Patreon if you want, mainstream media outlets profiled Milo endlessly, thereby conveying to the rest of us that this is someone worth taking seriously. And one of the reasons why mainstream media outlets were so obsessed with Milo and comparable figures is because he was their Walloigi. But he was the anti-Huffington Post, therefore you can create this ecosystem where it's like they're playing off of each other.

It's like, oh, Milo says all the naughty bad things that we're not allowed to. So we're going to profile him and give him more ammo to use because there's this like mutual effect to that. That's why the media ecosystem, why Milo became such a darling because it was like at the end of the day, all of it was run off of this same desire to get clicks and to get attention online. And because he was so good at that. And specifically in a genre that mainstream media was very responsive to, which was politics, that, in my opinion, is one of the reasons why Milo became this little media darling for that period. I also think as someone who has a whole podcast thinking about right-wing politics, intellectuals, and so on, I've noticed that for sheer, like, content creation purposes, more mainstream outlets have to find some right-wing figure to profile, inevitably in a way that, It might not be overtly sympathetic, but it always ends up being kind of a win for them at some level because we all know the right wing. Like it's kind of priced in some of the nastiness.

So what they're gaining is wider exposure. Their ideas are being, you know, for every person like us who reads a profile of Milo in year whatever and is horrified, there's people who say, oh, wait, I never heard of this guy. This is kind of interesting. And it's kind of a tricky problem because it feels wrong somehow to ignore people like Milo because they are spreading vicious, hateful things. Their politics are notches. But if you cover them too much, it's kind of a win for them because it's, it's, you know, kind of in-kind contribution to their PR campaign. I just think if you are going to cover these figures, as I do, as both of you do, on our respective, very established media properties. But like, if you're going to cover these

figures, you have a responsibility to do it honestly, to weigh the harm that they're causing, to not treat it like a joke or, I think perhaps even worse, something like serious and fashionable. And that brings me to one particular profile of Milo Yanopolis. He was put on the cover of Out magazine in 2016. Out Magazine is probably the biggest LGBT, like media property. And it wasn't like how horrible is this person. It was like, this is a relevant gay guy. So we're going to do a fashion photo shoot with him. And I want to look at some of those photos.

The article, the accompanying article, was titled, Send in the Clown. Internet supervillain Milo doesn't care that you hate him. It's so annoying. Internet supervillain itself is a bullshit term. Yes. Or descriptor. Like that makes it seem.

a little cool or at least like something you don't have to take that seriously. Yeah. Right? Yes. Yeah. Ooh, super villain. Could you just describe the photos that we're looking at? And if you're watching the video version, I'll throw it on the screen.

I mean, I literally gasped when I saw these pictures because I was just like, you have got to be fucking kidding me. They are like glamour shots. Like they have put him in these elaborate costumes. In the first one, he's dressed as a clown. and he has like the classic like clown makeup with like the blue diamond face paint on his eyes like little red hat and like retro clown suit on but even in this photo it's like they're shooting it like he's a movie heartthrob they're shooting it like he's like a sexy like clown I hadn't I hadn't either didn't see or didn't remember that photo shoot and Matt when you sent them around beforehand like I was like what the How is this even? Like, it's bizarre in a way that I, words are failing me. Like, it's just very strange, the clown, but it does have the effect.

Whatever else you think about these bizarre photos, the clown get up is a way of saying, yeah, this isn't that serious. It's so annoying to me. And also for Patreon, Kat and I did an episode about Barry Weiss. And it was like New York Magazine or like one of these, like very fashionable, trendy publications, did a similar piece and a similar photo shoot of Barry Weiss, where I'm like, this photo shoot and all of the people you paid to create it and the makeup artists and the set designers and everything cost thousands of dollars.

They look on top of the world like someone you would want to be. And interestingly attached to this article about Milo Unopoulos, Out Magazine put a disclaimer that was like, just because we're covering someone does not mean we endorse everything that they've ever said. And I'm like, well, based on how you've presented, of the material, it sure looks like it. The fact that they had to say that. Yes.

Someone felt compelled to insert that is kind of like the tell, right? That's their conscience or something peeking through. I have included a passage from the article. I want someone to read it. Enter Milo Yanopolis, a 32-year-old, shamelessly gay, British Catholic of Jewish descent, who now lives in Los Angeles. He stands over six feet tall and has a lanky soft build. When he's not dressed in tailored English suits, he's usually sporting tank tops, flowy textiles, straight-legged jeans, and a thousand-dollar Nike basketball shoes.

Quote, I wear these because the guys I want to fuck know what they are but can't afford them. Dark sunglasses, his signature strings of Bahamon pearls around his wrist, and a pair of gold crucifixes about his neck. He has poor eyesight and is constantly reaching for his glasses. When he speaks, he lowers his chin and leans in intently, fixing a gaze with dark eyes that are at once dough-like and cutting. Shut up! They're all like, he's at the airport. Someone screams at him, but he doesn't care and flicks through Instagram on his phone. I'm just like, shut up.

These people aren't that cool or interesting, but you're telling us that they are. Oh, he reaches for his glasses? Yeah, he reads He's just like me I remember in the Barry Weiss profile They were like She couldn't believe that she had accidentally gotten pen on her shirt Oh my God, she told me

I have pen on my shirt Who cares? That's incredible It gives the game away that they like him It really is revealing that they think he's cool And sophisticated and interesting and intriguing And it's like they don't care Whoever wrote this piece, I find it very difficult to believe, would actually care about Leslie Jones getting harassed off of the internet as a result of this man.

Which, by the way, this was published two months after the Leslie Jones harassment campaign where Milo called her a man. Like, this was two months after that. Wow. That's incredible. How much of this, I do not intend to derail us with this, but Americans falling for any, with a semi-charming British accent remains undefeated, it seems like. Well, actually, that's a good segue

into the next time we're going to talk about. Because in his earliest days, despite all of the abhorrent shit he was saying, he was charming. And he could charm the pants off of a live studio audience. And he did that very thing when he was invited to speak, of course,

on Bill Maher's show. A few months, after this Out Magazine profile, Bill Maher was one of many people who gave him a sort of primetime interview. I think that that interview is instructive for a few reasons, and I want to play a couple brief clips. The first clip is just an excuse for me to lay into Bill Maher. I'm for it. You look like Bruno. You know, I told her to dial down the contouring. She didn't listen. Your makeup lady was just crazy. All right. About a year ago, people started.

started to tell me, are you going to get this guy, Milo, you know, on your show? And I started to look into, you know, what you're saying. And look, I think you're colossally wrong on a number of things. That's okay. But if, exactly, if I, if I banned everyone from my show, who I thought was colossally wrong, I would be talking to myself. Bill Maher is like, I need to talk to people who I disagree with. Otherwise, I wouldn't have a show. Bill Maher, when's last time you talked to a leftist? Bill Maher, when's last time you talked to a Palestinian about Israel-Palestine? It's so fucking, again, this is nothing to do with Milo Unopolis. It's just so fucking bullshit because Bill Maher loves to create an aesthetic of like, I'll talk to anyone.

But I'm like, no, you won't. You will only talk to people at least as right-wing or more to the right than you are, because that's who you're most comfortable talking to. And he does this thing with this specific Milo-Yanopoulos interview. where he sort of creates the aesthetic that, like, they have nothing in common and they are so different. But not five minutes into the interview. They're bonding over how much they hate Muslim people. No, I like to think of myself as a virtuous troll.

But if somebody gets hurt because of truth needs to be said, like religion. I've always attacked religion. Well, your sound on Islam, unlike most of the people on your side. Yes. Right. That's true. Milo is, like, grinning from ear to. to ear during this televised interview because this gives him everything he needs. Matt, you, I think,

made this point earlier where it was like, if you are giving these people a platform, then they can sway nonbelievers, even if the people who are watching think they disagree with them from the outset. He's doing his whole charming, funny schick in the beginning. And then he's like, it's okay if you disagree with me. It's okay if you disagree with me. Is manipulating the audience and Bill Maher is giving him a massive platform to do it. And by the end of this appearance, many people watching are going to be like, you know, I may not agree with Milo Uniopoulos on everything, but what a, what a charming little man. Like, what an interesting guy. Maybe I actually do agree with him on some stuff. And maybe the media is wrong for saying all

these things about him. Yeah, Matt, I like to say, I really love your Bill Maher hate. You know, there was, there was a, there was a, I know, I know. There was an old writer for The Nation magazine who every summer when he did get a new intern, you know, he would ask them, like young man, young woman, is your hate pure? And your hate for Bill Maher is pure. I'm glad you played that clip because Milo is very charming in that clip. This is part of the, why he's such a dangerous faggot. He lives up to the name. He lives up to the name.

And I want to play another one for you. So let's start with the contradictions about you, which is pretty crazy, because you're gay and your... Spoiler alert. Oh, come on. You can do better than that. What tipped you off? I've been reading about you. I mean, your mother's Jewish.

You have a black Muslim boyfriend. No. But I haven't heard one now. You did. Still black, not Muslim. Not Muslim. But he was Muslim? There was somebody once.

Okay. But you spoke about... We don't talk about it. You've spoken out against all these people. Like, you say, you don't hire gay people. Oh, no, you can't trust him to shop to work on time. Too much drugs, too much sex. They never show up to work.

Always making excuses. No, no, no. I mean, not as bad as women, but no, I don't hire kids. But you know, that's not... I mean... Oh, there we go. But, you know, that's just... Just kidding.

You're easy. You're very easy. Very easy. easily triggered. It's pathetic. I mean, it's the same thing. It's like he's funny and then he'll like push it a little too far and then he'll be like, oh, but I'm just joking. You guys are so triggered. He's not joking. It's not funny. His actions and rhetoric that he spread, we can now see with the benefit of 10 years in the future, how many horrific consequences they had for actual people's lives. But this studio audience is just like eating it up. I know. That was, that was, I

just as mad at them. It's like, listen to those piggies eating up the slop. Terrible. Again, this just circles back to how much I hate Bill Maher. Yeah. Most things do, in fact. As it should. Milo's having fun, right? He knows what he's doing. He's very good at it. Like I said, he's charming this audience, which if he just came out and said, you can't hire women or gay people because they'll never show up for work or do the job, that's horrifying. But Milo's presentation is very convincing. So he knows what he's there to do. And so does Bill Amar, and it's good TV, and this video got 7 million views on YouTube. And this is how people worm their way into the culture. And, you know,

Bill and Milo, despite Bill going great lengths to define their aesthetic differences, do have a shared goal, which is getting attention. And this is also after the Leslie Jones incident. Like, man, shout out to Leslie Jones. And just all of the people who were, overlooked during the rise to this man's fame as just people who are worthy of being sacrificed at the altar of like, but he's so cute and funny. Yep. Vute is completely disposable. And then people like Bill Maher get to act like they're so different from Milo Yanopoulos, like get to frame this whole thing as like, I really disagree with you and we're on opposite sides of the issue. What, what sides of the issue do you not agree on? What is he saying that you disagree with? That's such a,

That's such a great point. It ends up being this weird way in which Bill Maher, like, having Milo on is proof of his principles and virtue or something actually. Like in his telling, like that actually is what that proves. It's not that you're platforming this odious bigot. It's that, no, see, I, Bill Maher, I talk to people I disagree with. In this age of, you know, polarization, look at us having conversations across the divide. Fuck off. Sorry.

Such fucking bullshit. No, no, no. Get into it. Get into it. This is where we yell. It all comes back to the imaginary victimhood versus real victimhood that we talked about at the beginning. So as Milo's star continues to rise, he does sort of become a MAGA darling. Milo was good at generating press about himself and his movement, speaking at campuses across the country and working to legitimize the alt-right within what was becoming mainstream MAGA culture.

One such speaking event at Berkeley College in California famously drew 1,500 protesters and became violent with many people getting beat up and injured. But this was good for Milo, because his fashioning himself into a warrior for free speech absolutism earned him credibility within members of Trump 1.0 and a speaking opportunity at CPAC 2017. This was, you know, of course during the era when Republicans claimed

to be the party of free speech in opposition to the cancel culture-obsessed liberals. Nowadays, those rules have decidedly been reversed. His invitation to CPAC was supremely controversial from the outset regardless. Traditional Republicans, like Ted Cruz, tried to eschew Milo from the movement, finding him cruel and obscene. But the movement was decidedly gravitating towards the brashness and outward race. of figures like Trump and Milo, so they fail to stop him. I want to give a content warning now because we are about to talk in some detail about child sexual abuse. In 2017, Milo Yanopolis

was preparing to speak at CPAC when video surfaced of YouTube interviews from the year prior, where Milo had argued that some 13-year-old boys could consent to sex with adult men because some of them are, quote, emotionally mature enough to consent to sex with adults. The law is probably about right. That's probably roughly the right age. I think it's probably about okay. But there are certainly people who are capable of giving consent at a younger age. I certainly consider myself to be one of them.

People who are sexually active younger. This is one of the reasons I hate the left. I remember this sort of stupid, you know, one size fits all police. of culture, this arbitrary and oppressive idea of consent which totally destroys, you know, the understanding that many of us have the complexities and subtleties and complicated nature of many relationships. You know, people are messy and complex and actually in a homosexual world, particularly, some of those relationships between younger boys and older men, some of those relationships are some of the most...

It sounds like... It sounds like... Yeah, well, you know what? It sounds like Catholic priest molestation to me. You know what? I'm grateful for Father Michael. I wouldn't give nearly such good head if it wasn't for him. Oh my God. This was a bridge too far.

Simon and Schuster canceled plans to publish his autobiography called Dangerous, which he had previously received a $250,000 advance for. He resigned from Breitbart under pressure, and CPAC canceled his speech. In the wake of all of this, yet another 2015 interview clip emerged where Milo told Gavin McInns, the co-founder of alternative media outlet vice, who himself turned out to be a neo-Nazi, the 2010s were crazy, that child sexual abuse is, quote, really not that big a deal.

You can't let it ruin your life. But as far as I can tell, it did ruin his life. I want to play you guys the apology, the rare, the exceedingly rare apology that Milo made in the wake of these clips resurfacing. and here's what he said. Between the ages of 13 and 16, two men touched me in ways they should not have. One of those men was a priest.

My relationship with my abuses is complicated by the fact that at the time I didn't perceive what was happening as abusive. But I can look back now and see that it was. I still don't view myself as a victim, but clearly I am one. My experiences as a victim led me to believe that I could say almost anything on this subject, no matter how outrageous.

But I understand that my usual blend, of sassy gay British sarcasm, provocation and gallows humour might have come across as flippancy. A lack of care for other victims or even worse, it seems to have been the case in reports. Advocacy. I'm horrified by that impression. I would like to restate my disgust at adults who sexually abuse minors. I regret the things that I said. I don't think I've been a sorry about anything my whole life. And this isn't how I wanted my parents to find out about this either. But let's be clear about what's happening here. This is a cynical media witch hunt from people who do not care about children.

They care about destroying me in my career, by extension, my allies. They know that although I made some outrageous statements, I've never actually done anything wrong. They held this story back. They held the footage back. Footage that's been out there in the wild for over a year because they don't care about victims. They don't care about children. They only care about bringing me down. Additionally, Milo told the New Yorker, quote, I don't believe sex with a 13-year-old is okay.

When I mentioned the number 13, I was talking about myself. I was talking about the age that I lost my virginity. I think anyone who is tuned into politics or was like watching the news a lot at this time remembers that Milo defended pedophilia. And that was the story. I did not know until I went back and looked at all of this for this episode that he later explained it this way. And I think it colors in so much of what we know about his life.

My first thought when I hear him talk about this and sort of his rationale behind it is that it's not super uncommon. And in fact, over the past couple of years in my reporting, something that I've gotten really interested in is this phenomenon where people who are victims of abuse, whether it's childhood, sexual abuse, like the type that Milo is describing here. or whether it's, you know, intimate partner violence, domestic abuse, I've noticed that a lot of times people will come out of these situations and they will develop really, really victim-blaming attitudes in response to being victims. And I was like, where does that come from? Because I see it all the time. And the refrain usually is not as horrific as Milo's commentary on children. It's usually something like, oh, well, I'm a victim of abuse and I don't believe her or him or them because I don't think what they went through is that bad or that's not how I would have acted

or yada, yada, yada. And I actually spoke to a sociologist about this last year who told me that one of the reasons she thinks this is is because when you are a victim of something, very rarely do you get anything even resembling justice? Like that rarely. That rarely ever happens. We live in a very backwards world when it comes to abuse. Typically, abusers don't really face any consequences and sometimes they even assume benefits as a result of them abusing others. And so as a victim, and I think particularly as a child victim, how do you internalize that and how do you grow from that and what does that do to do your mindset? I think a lot of times in order to cope, people do flip it and say, like, well, I'm not a victim. And I'm not a victim. And

actually what happened to me wasn't even bad. And that's exactly the way that Milo was describing these incidences. It's just that that doesn't justify or make it okay for you to spread that type of victim blaming language further. But I think that that internal sort of psychology around this is really, really, really common. And the sociologist who I spoke to found in her research that it happens more often than not. So that was kind of my first impulse here. I also suspect that that at the time he was making like this press conference, there's no way that he would have actually been able to like heal and reprocess all of this stuff from the time that the podcast resurfaced and he got fired and the time that he was making those statements.

Like it's not that he was being coerced into saying like, actually I am a victim and actually like what I said was wrong, but I doubt that he actually believed it, which I think helps provide color as to what will happen next in this timeline. The last thing I'll say is when he mentions that people bringing this up, actually care about children and it's all a very cynical like media ploy. There is some truth to that. I literally wrote down in my outline, that is true. That is true.

There's definitely some truth to that. Like some of the people who were outraged about this online and I remember this happening. And to your point, Matt, I don't really remember like all of this, but I remember him making these comments. A lot of people were justifiably outraged about it. But you think about him getting pushed out of Breitbart, Steve Bannon's operation. And just recently it was revealed that Steve Bannon, and had a very close relationship with Jeffrey Epstein throughout all of this.

And it was working behind the scenes to help try to, like, allow Epstein to have a comeback into polite society. So it's like, yeah, what Milo said in that podcast, the language he used and the framing he used was notable. It was something that you don't hear every day. But the attitude he's espousing is not that abnormal. And it is deeply interwoven into the conservative movement and beyond. Yeah, and held deeply by many of the people who sought to push him out. And so much of this was about aggrieved conservative media figures who thought that Milo's brand of conservatism was going to make them irrelevant. Kat, could you say what when someone like Milo says, I am not a victim? What does that do for them?

Or what is that compensating for? Yeah, obviously, you know, I can't speak for him directly or for every person. but the sociologist all, like, cited the person who's research into this, I find really helpful. It's a book called On the Wrong Side. And the sociologist in question is Nicole Bedera. And she did these interviews with people going through the Title IX process where she would interview them before they started the process, like after they had just been assaulted or abused. And then they would go through the whole Title IX process. Every single one of them unanimously in the entire school system that she studied over the course of a year, every single one of them was filled by the system.

which is striking on its own. And then she would interview them again at the end of it. And a lot of them, what happened to their thought process was they kind of determined that they weren't victims. Because the alternative to saying like, if you say like I am a victim and I was filled by the system, that is really haunting and difficult to carry with you. And victims who internalize that they are in fact victims, which is true, often suffer more consequences. than victims who flip it around because the people who went through this system and were failed and who knew that and continued to believe that, a lot of times they would drop out of school, they would struggle to complete their degrees, and they would just struggle to be able to move on

because they knew they had been failed. But victims who decided that actually it was their fault, and actually they weren't victims at all and the school was correct to fail them in this way, those are the people who would be able to stay in school and, like, complete their degrees. So it's almost like a survival mechanism. Yeah, I was going to say that that's exactly where I was going to go. It's like there is something almost empowering about saying, I'm not a victim and moving forward. But the problem then is the actual stuff is not dealt with.

And that's not being critical. It's hard. It's obviously just beyond difficult to handle those things. But it does mean like someone like Milo, as he was going through his life, it was all kinds of undelt with traumas and difficulties that we can sympathize with, but also kind of saying I'm not a victim. It means it's kind of like you're moving forward but without healing at all. And that's.

Yes. It's probably going to lead into what you might want to say next or where this tale is going to some degree. I mean, I want to provide compassion with the caveat that a lot of people do experience things similar to what he experienced and don't end up doing this. But at the same time, like, the compassionate part of me is like, well, maybe if he wasn't abused by a priest when he was 13, maybe he wouldn't have flunked out of school twice, you know, and maybe he would have gotten a normal job instead of filtering into this like shock jock conservative media persona thing. And if that had all happened, maybe he would have had space to deal with this in a healthy, way that could actually allow him to heal. But he didn't have any of those things. And perhaps because

he was already down this right-wing media persona career path and this is all he could do and perhaps also as a genuine coping mechanism that felt good to him at the time, in 2018, the following year, when Milo is decidedly out of work, he self-publishes another book called Diabolical, how Pope Francis has betrayed clerical abuse victims like me, wherein he attempts to assert the discredited link between homosexuality and pedophilia. Milo blames systemic child abuse in the Catholic Church, not on closed-rank power structures

or a culture of Christian sexual shame, but on a Pope, he views as overly friendly to gay people and progressive bishops, he refers to, as the Lavender Mafia, which is another good name. This comes up again in 2024, when he still seems to just be really upset about the things that he said and I think specifically what they did to his career. He tweeted, at 13, I was raped by a priest. His name was Father Michael. He died years ago. I said some stupid shit trying to make sense of it, which was used against me in 2017. The idea that this translates to Milo is a pedo is so warped and dark that anyone who says it

is dead to me forever. Well, I mean, to me, when Milo said that these people in the media don't actually care about abuse victims, what is he doing there? So I can honestly say when I was an editor to Catholic magazine and the summer of, I believe, 2018 is when the sex abuse crisis really reemerged in the news because Cardinal McCarrick, right, who was a very faith, he was the Archbishop and Cardinal of Washington, D.C., very major figure in the American Church, his decades, long abuse, especially of like young seminarians or like priests in training, came to light. And Francis happened to be Pope, who did not make Cardinal Mcaric a bishop or an Archbishop or a cardinal, right? He was, Cardinal McCaric was retired basically by the time Pope Francis, this time

period we're talking about. But I can honestly say no experience of mine in media has made me more depressed, despairing, just, just almost sick to my stomach than using priests abusing children to try to do a coup against Pope Francis because you didn't like the direction Pope Francis was leading the church. That to me is just unfathomably evil to try to take out a Pope who he has flaws. And when it comes to handling of sexual abuse by Catholic priests, I've written about that. I've written editorials about that. I'm not letting Pope Francis off the hook, but he was not the heart of this problem.

Nothing that happened to Milo had anything to do with Pope. Francis. Pope Francis was a normal straight guy, which is why he didn't give a shit about when he said, who am I to judge? He was almost like a straight guy saying, I don't get the big deal because he's not neurotic about it, right? That's why Pope Francis was able to be somewhat normal toward gay people compared to many other popes, because I think he just, it didn't, you know, it didn't trigger any kind of his own neuroses or repression like it might have with Pope Benedict the 16th and his red Prada loafers and such, right? So that's one thing I just wanted to say that the very thing Milo was criticizing that statement, you know, he was doing, he was using the, you know, survivors of abuse to try to take out a Pope who his ideological allies hated no one more than Steve Bannon. Like Steve Bannon hated Pope Francis with a passion. He viewed him as like the er globalist enemy of whatever he was trying to achieve politically. And so I find, I just wanted to say that. Like I have no tolerance. when it comes to sexual abuse in the Catholic Church. But I find leveraging the suffering of victims and survivors that way, really disgusting. And of course, Matt, as you pointed out, the link between pedophilia and homosexuality is discredited. The link between gay priests and abuse is not real. None of these things are real that he's claiming.

There are problems in the Catholic Church, including with gay priests and the kind of culture and secrecy around that. But that is not, that's like an institutional structural problem, not a gay problem. problem. And so I just want to say, as someone who has thought about and read about these things far too much, please do not take anything Milo says seriously. If I can convey one point on the Catholic question, he's almost every single point. It's just the opposite of the truth, in fact. And I do think like the Milo Catholic media tour, kind of this phase of his career, which seems very connected to Catholic matters, I remember, I mean, again, going back to the 2016 era, When I started as an editor to Catholic magazine, I became aware of this gentleman named Michael Voris, who I always thought seemed very gay.

And it turns out, like, as his story came along, he was, like, formerly lived the gay lifestyle, right, the homosexual lifestyle, but then stopped. And he ran a media operation called Church Militant, which the SPO Southern Poverty Law Center describes as a ultra-Orthodox Catholic propaganda ministry that pushes an anti-LGB. agenda on the episode entitled The Pope and the Homo Mafia. The two, meaning this guy, Michael Voris and Milo Unopoulos, discussed the book you mentioned, Matt, diabolical. And it's just one of those moments where, like, as a gay Catholic, I've made a promise to myself, to be honest, when, like, I've told Cardinals, important ones that I'm gay, like at a cocktail hour. Like, I take every opportunity I have, every priest I meet, every kind of Catholic, you know, prelate people in the hierarchy. I tried never to hide it. And so I found it especially appalling that these two gay men,

right? We're sitting there talking about how they're not really gay or they've stopped being gay and how the gays are the problem with the Catholic Church. It was just like a distinctly Catholic form of absurdity, actually. Like probably you're only really going to get that these days with any regularity in religious context where the guys who are white knuckling it saying, I'm not gay, I prayed away the gay, whatever it might be. right. They're continuing to build the cage that they're trapped in, you know. And it's just, it's both kind of comical and absurd, but also deeply sad because they're lying about themselves and they're lying about the church. And when you're building your life on lies, it crashes out

in the way it has with Milo, among others. Speaking of, the 2017 pedophilia scandal was the effective end of Milo's short-lived relationship with the mainstream right. Since then, he's bounced around looking for work, working underneath figures, including Kanye West, who he served as chief of staff for in Kanye's short-lived 2024 political career and for Marjorie Taylor Green. Unpaid intern, correct? Was Milo unpaid under Marjorie? I read that in preparation. He was in like 2022, he was an unpaid intern for some amount of time with Marjorie Taylor Green. What I do know is that he lived in her house.

Crazy. Oh, man. Room and board was included, but no excitement. I know. This is a great premise for a sitcom. Yeah. Yes. A Milo-like character and a Marjorie Taylor Green like character, you know,

two's company. I'm a fascist woman and here's my gay live-in intern. It's awesome. Yeah, yeah. Milo claims that he helped orchestrate the infamous Mar-a-Lago dinner between Trump, Nick Fuentes, and Kanye West to get back at Trump or putting him in political exile, knowing correctly that the dinner would be a PR fiasco for MAGA. Milo has also traversed the podcast circuit to advertise his conversion out of homosexuality,

and it's up to you to decide whether that is an attempt at sustaining relevance and pivoting the brand or a product of genuine religious psychosis. talk about his sexuality. In 2017, when things were still going well for Milo in his career, he married his husband, a black gay man. And there isn't much known about his husband. And Milo posted photos from their wedding, where his husband is turned around in every photo. Wow. Which is bizarre and also speaks to Milo's just ongoing objectification. of black gay men, even on his own wedding day. But I also understand that this guy probably wanted anonymity because...

I would if I was married to my... Right. I mean, it's like I understand why we're doing what we're doing here. Yeah, yeah, yeah. But despite his marriage and his flaming homosexuality in general, Milo insisted throughout this entire thing that homosexuality is a sin and criticized the Catholic Church's loosening attitude towards it, saying, quote,

I wouldn't dream of demanding that the church throw away her hard truths just to lie to me in hopes I'll feel better about myself. And if it's no longer a sin, then your whole shtick is kind of blown up, isn't it, Milo? I feel like this is sort of like a progression that you see happen in conservatism, where it's like not by any means all conservatives are stemming from the root of like unresolved abuse or trauma in their lives. Hashtag not all conservatives. But some certainly are. That is why I believe that Trump as the abusive father figure for all of America has taken on such an important like cultural symbolism in the new right. Like we're all treating Trump as our abusive father.

What I feel like is kind of happening with Milo is like he really internalized this idea that he wasn't a victim. Then he was forced to confront the fact that he was a victim and take that on as an identity that he didn't actually believe or was like processing. And now we have this phase where it's like, it's so much easier to blame the Pope and gay people punching down or up, like in a weird way, like tokenizing in one direction and like punching out in the other direction.

And it's like that's so much easier than actually having to process and understand like rape and abuse culture, which is all around us and deeply depressing. And for Milo likely the root of a lot of unresolved issues internally. So it's like now we've entered the ex-gay phase because we're just, he's constantly moving from one form of disassociation around that childhood trauma to the next. Yeah. And that is exactly why I said. It's like, is this religious psychosis in dealing with trauma?

Is this just where you are in your career, which you would also have to throw away if you admitted that why what happened to you happened to you was not because of gay people. It was not because of a, you know, relatively liberal Pope. It was because of all of these institutional structures of power that we are constantly criticizing on the left. Yep. In 2019, Milo was a still openly gay, but also the Grand Marshal for a straight pride parade in Boston. Throwback to that era of the culture were, remember when they were like trying to make straight pride a thing? Yes.

In 2021, Milo declared himself ex-gay. He said that he was opening a conversion therapy clinic in Florida, not sure if he ever got around to that. He said that his husband, which he still had, had been, quote, demoted to housemate. Oh. They are currently an active divorce. I cannot imagine why.

Ex-gay is back. I mean, we've talked about this before, Matt. Like, we've talked about this on the channel. Yes, we have. X gay is back with a fervor and a passion. And it is quite frightening the number of people. Even just, I think, like a reality TV star just this week came out as ex gay. Or like he said he was renouncing being gay and now he's a girlfriend.

It's just like it's happening all the time. It's making a comeback. But then also like talking about, you know, people who supposedly believe in free speech. It's like they're making like a free speech, free association argument. know why perversely, like you should be able to send, like, I don't understand how it's free speech to make sure your like 14 year old son can be stuck in, you know, therapy with some lunatic who tries to get him to pray away the gay. But it is like, again, like hypocritical free speech arguments among other things are in this tune. But they're actually winning like court battles now as Trump reshapes the judiciary, like certain states, yeah, like practices that had been banned or outlawed, right? Or severely curtailed in terms of reparative therapy are back.

And it's really, quite frankly, it's very depressing to me as a gay man, especially for the poor guys, you know, whose nut job parents are going to make them suffer through that. Yeah, my first boyfriend when I was in high school, his parents put him through conversion therapy. Mine too. Do you guys remember that Bill Maher interview I showed you and how Milo was, despite all of the insane things he was saying, like, charming, playing to an audience, coherent, aware of all of his camera angles. in December 2025, eight months ago, Milo went on Tucker Carlson's show to discuss his turn away from homosexuality. And I'm going to add another content warning here for some graphic descriptions of modes of conversion therapy. Let's watch a clip. I just woke up one day and I was like, and I was married to a dude, to my shame.

And I, who's now like the ex-wife from hell. Oh my God. Look, if there's no other reason. to like not be gay. Just imagine like how bad a black homosexual ex-wife is. Oh, like, I'm not even going to go there. You don't even want to know. It's like, oh, sorry, it was two sports cars a year, it wasn't enough. Okay, all right, okay, all right. Don't even. But when I woke up one day and I,

I woke up one day and I looked over, and I was like, oh, no, I don't want to do this anymore. Like, hell is real. I don't want to go there. And it just hit me like all after, it was growing. You know why? I was just like, no, no, I really don't want to go there and I know. What am I doing? And the way that I started to address this, I kind of stumbled upon a crude version of what the enlightened, like they don't call it conversion therapy anymore. They call it reintegrative therapy because it's reintegrating those shards and those and those broken and those broken bits of like memory that lead to the wrong output. Well, you're talking about detail if you want to, but I, I, I, I. I stumbled upon kind of like a crude version of that.

So when I was trying to stop myself from doing this stuff, I was using like hot oil on my thighs. I was like doing things, you know, like like, like the hurt. And I was trying to rewire my brain. Because I read a lot of, you know, psychology, anthropology books or stuff like that. I thought, I don't know what. Sex urge is such a basic and powerful urge. It's got to be hard. I thought I knew what I was doing.

So I was like every time I get aroused, I'm going to go and do something that hurts. Matt, how many views does that have? 250,000. That's pretty bad. It's pretty bad. And there are thousands of comments on it being like he's clearly like struggling, may God grant him the power to get through what he's going through, et cetera, et cetera. Matt, is that struggling what you kind of are referring to when you pointed out how kind of articulate and aware of the camera angles and kind of on point he was in the prior interview? Are you, were you kind of like juxtaposing even his manner? Like there is a decomposition. even if you hadn't seen the Bill Maher clip from earlier, you just watched that clip. He's not a well person. And I don't mean that in a mean way.

I just mean he doesn't talk the same way. His thoughts are more broken. He's clearly been going through some stuff in a way that is like that, that Milo is not nearly as compelling as the clips we saw earlier. And I say that, again, just because I think that was one of the things you're driving at. Absolutely. And it really struck me because I, you know, before planning this episode, like I haven't watched a Milo Unopoulos interview probably since 2017 when he sounded a lot like how he sounded in that Bill

Marr interview. And when I was watching this Tucker one from more recently, it struck me like, you know, I can't say definitively if someone's on drugs or I don't want to armchair diagnose anyone with anything. But clearly, a great deal has happened. And this person, is broken. I mean, the sort of irreverent, cruel, one-liner humor that many people once found charmingly offensive in the 2010s now just feels sad. I mean, even when he is clearly trying to make a joke about having a black gay ex-wife, Tucker is like not laughing. He's like, I don't even want to go there. Do you know what you have to say for Tucker Carlson to say, I don't want to go there? Yeah. Literally. Yeah. I mean, seeing this and knowing that

a quarter of a million people watched it and that many of them are agreeing with this direction that he has taken is just a really disturbing reminder of one of the reasons why the X-Gay movement takes on a lot of steam right and out. Back in the 90s, which I think was the original, like, peak. Yeah. Like, certainly pre-internet was the original peak of the X-Gay movement. Then it was like books and speaking tours and like mega-churches and like a religious movement. But now it's an algorithm-driven movement that is held off by like podcasters with massive platforms like Tucker Carlson. It can reach so many more people. And as depressing as this is to us, it's sending a terrible message to like closeted or gay people who are watching this who are in this audience who are like, you know, seeing it as something that's being presented as like admirable and part of a struggle that is necessary.

Yeah. And I actually want to amend to that number. because I was referring to Tucker had just posted that clip, the full episode that he did with Milo titled, Why Are You Gay? Milo Yanopoulos explains has 1.3 million views. Yeah, that's really bad. And I mean, like, I get this stuff on my Reels.

My Instagram Reels, I get like ex-gay and ex-trans stuff. And I'm like, why is this even being targeted to me? Like, I'm not ex-gay. I'm more gay than ever. Yeah. And I want to add, too, it's interesting. how much his story of like waking up one morning, right, and almost in an instant having a specifically religious insight, right, not wanting to go to hell. That is so, he may talk with a

British accent, but that's so American, right? Being in a moment, you can change your life around on your deathbed, right? You can ask Jesus into your heart. And especially if you ever want to get away with something in our culture, you say, I was wrong, but I found Jesus. I'm forgiven, and I'm moving forward. It's the Russell Brand move. It's the last Christopher Hitchens. 15 years ago in December will be when he died. After Jerry Falwell died, he had the great line. He said, if you can just get yourself called Reverend in this country, you can say stuff

that no one else could get away with. And I thought of that line when Milo basically, you know, it's the ex-gay and the religious conversions, they're kind of like two sides of the same coin or often they go together. right or whatever your sin might be but it's i found jesus i'm a new man so quit complaining about me and let me continue to sell you now religious artifacts or whatever that russell brand you know the russell bible or his necklaces with pendants it's just all kinds of you know it's the beef tallow yeah yeah yeah yeah it all fits it's also like with him being like i don't want to go to hell hell hell is real I'm like, baby, you're in hell right now.

You're in the realest hell you're ever going to experience right this second. Yeah. It's very Dante, right? The people in hell who don't realize they could leave. Yep, exactly. Well, one thing about leopards, they stay hungry. Throughout all of this, Milo's support for banning immigration has never, ever, ever, ever, ever wavered. This has been one of the tenets of his politics from the very beginning,

and, you know, I should say not banning immigration in general, but banning immigration of brown people. That's what it's always been. In I believe 2017, he gave one of his many campus speeches at Boulder, Colorado, where he held up a sign that said, Dear Trump, please deport fat people. But then more recently, in 2025, he tweeted, California needs ice checkpoints at supermarket entrances,

gas stations, strip malls, intersections, and government buildings, with on-the-spotation for anyone who can't prove they are in the U.S. legally. And then in September of 2025, total legal immunity for ICE agents when they're on duty. Milo Yanopoulos, an immigrant, was arrested by ICE on August 27, 2020. at the Louis Armstrong New Orleans International Airport, where he was arriving ahead of a scheduled Kanye West concert because I believe he is still working for Kanye West.

I mean, you do what you got to do. Never before heard sentence. The Department of Homeland Security announced his arrest over Twitter and shared his mugshot where he doesn't look like the Milo you remembered. Unrecognizable. Now, almost immediately, fellow right-wing provocation. Tour Islamophob, pro-Israel sycophant, and friend of the president, Laura Lumer, claimed responsibility. Writing on Twitter, breaking, illegal alien Milo Yanopoulos has been detained by ICE.

I was the first person to report on the fact that Milo was in the U.S. illegally, where he incited violence against President Trump and worked for Marjorie Trader Green. Recently, Candice Owens invited this illegal alien into her home. When Milo called for me to be assassinated, I reported him to ICE and the FBI. I told you all that Milo was an illegal alien. He was detained in Louisiana by at ICEGov. Milo is going to be deported back to the UK where he can live among the Muslims he has recently chosen to embrace. Today is a great day for America.

Now, it's worth noting that Milo and Laura Lumer used to be great friends, But in recent years, that relationship has soured both politically. As I said, Milo became an ally to Marjorie Taylor Green and the burgeoning anti-Maga America First Right, which is critical of Israel. Israel is something that Laura Lumer has hitched herself to. But they also seem to have had a personal rift. Milo claimed on a podcast that Laura Lumer wasn't really Jewish, that she was just claiming to be. He claimed that Laura told her friends that she'd performed a sex act on the president. And he claimed that Laura had been 5150ed, which is an involuntary psychiatric hold when she was younger by her father, which is the real reason she can't own a gun. Why any of this is anyone's business, God only knows. And so it's just like, these are all pitiful, spiteful, shameful people with entirely too much power. I mean, I just, people were like, you know, this is the one time I can support ICE, I guess. And it's just like Laura Lumer has the power to get him deported because she's personally had it with him. That's crazy.

Yes. Can I read from my great friend, John Gans, who did his great substack, unpopular front, great name. But he summarized it this way, which I think is really important to underscore. Here's where the wry smile of Shaden Freud must give way to the furrowed brow. On its social media sites, ICE publicized its deportation, a mugshot of Milo. Think about it. The security state is being used to settle factional disputes in the ruling party. And apparently, at the behest of a person who makes the screeching gobbles seem like a paragon of steadiness, manifestly insane and idiotic people are running our government.

They're using its tools to punish and humiliate their enemies. What country are we living in? I could not have put that better myself. I think that's the key point. The ruling party is using the security states to settle its factional disputes, which is what arresting and deporting Milo, what its kind of substantial meaning is. And I would just add, he's still getting special treatment. Why was he not in some Honduran jail? Why was he sent back to the country? He's actually from, right? Which is not something most people ICE is arresting something we can say they're doing. Oh, no. Oh, no. Oh, we lost Matt. He'll be back. I hope his laptop is a Okay. I'm going to text him. I'm going to say, okay. Oh, oh, there he is.

My laptop fell off of the pasta box and closed. Fuck me. Like, I... Anyway, upon returning to the UK, Milo gave Pierce Morgan a TV interview where he said, quote, I wouldn't wish this on anyone. I didn't really understand the physical reality of how institutionalized the brutality is in America. The manner in which they arrest you, they put your manacles, your hands, your feet, chain it together. I mean, like, everybody is arrested is like an MS-13 gang member, and it hurts a lot more than it looks like on television. You know, I was put from, you know, detention facility to a correction facility. You know, every three hours, they were sort of trying to keep ahead of my lawyer, so I couldn't. You know, so whatever. But no one would tell me anything.

It was, it, I mean, I know it's designed to be like that, but it's, it was, sure, it was humiliating and it was disorientating the rest of it. It was physically degrading. It was frightening. It was frightening. I don't think I've ever been frightened like that before. Just not, how emotional have you been through this period? I've never been like this before.

I tripped and kind of tumbled downstairs a night or two ago and, you know, and, you know, you you know, I'm a clumsy person so that it's not the rarest thing in the world. But it set something off from when I'd been kind of, you know, shoved down a couple of steps. And I was weeping like an old woman for an hour. And I was like, oh, I really have to get this out of my system. I think maybe in the past I've been a little bit, a little bit blaze when people talked about their trauma,

a little bit kind of cavalier when people talked about, you know, stuff kind of kind of lingering with them, but I get it now. and I wouldn't wish it on anyone. I mean, what is there to say? Yeah. What is there even to say? You spent 15 years making as much money as you could by specifically wishing this on everyone you thought was beneath you.

You did wish this on people. And like, I don't think that Milo Yanopoulos should have been deported because of a personal TIF with a colleague who has entirely too much. much power. But the situation you have here is one where, like, the machine that you very happily helped construct has set its sights on you. Yeah. I mean, how many times can we say the leopard ate my face? I think for me, part of this is going back to the question of like, at the very beginning of this episode, it was like, why are conservatives like so comfortable with this guy who was so flamboyantly gay, even though they don't like that? And I think part of the allure is, you know,

the idea that you can be conservative and you can benefit from these power structures, even if you can't. Like, that is why you have people from minority groups who are targeted by this ideology, throwing their full support behind it, profiting from it and pushing it further than it's ever gone before out of the hopes that they too can be a part of the ruling authoritarian class and crush everyone beneath their boot and that they won't be crushed. Like they want that domination and I think that appeals to people on like a very Intrinsic level where it's like oh well if this flamboyant gay guy can be a part of the the right wing ruling class then maybe I can be too But the end of this story is that you can't you can't be a flamboyant gay man who is so messy

You can't even renounce that and and be a part of the winners table there is no winners table like that's that's what people in the Trump administration tend to find out at the end of it. Is they're like, oh, it's not real, this, like, fantasy that I, that I've built by, like, wanting to crush all of my enemies. Maybe it's real for, like, Trump himself. But it's never, it was never going to be, like, what Milo pretended it was. And even the consequences that he's living with now, to your point, Matthew, are still nothing compared to the hell and the torture that he has put thousands of other people.

through. Have either of you heard this great definition of conservatism by Frank Wilhoits called Wilhoits law? Let me read it to you. Conservatism consists of exactly one proposition to wit. There must be in groups whom the law protects but does not bind alongside out groups whom the law binds but does not protect. But as Milo's finding out, you know, unless the law does protect everyone. No one is bound, right? Unless it's, unless it's, if, unless it's universal, both in terms of the binding and the protecting, it will eventually turn on you. That screw will turn. That worm will turn. Right. This is the universal politics we started the conversation talking about, right? Someone like Milo really thought there are some people whom the law should basically fuck over, bind, right?

Control, dominate. And those who should be free permitted to do the dominating, right? And, and, you know, punishing, basically. And he just found out, and if you start, once you start making exceptions, you will eventually be that exception yourself. It's like Lincoln's line in his letter to Joshua's speed, right? You start out by saying, all men are created equal except black people. Then it's all people are created equal except Catholics and Jews. And it's all, you know, you just, once you go down that slope, it just, you keep sliding. They don't stop because I say, oh, Milo's one of the good ones. So we're going to give him a pass. No, the machine he built chewed him up to. As I mentioned, I read so many of those glossy profiles they made of him in 2016, 2017,

and in one of them from Bloomberg, they talked about how much money he was making and how he would drop $12,000 in a single day on bespoke suits. And Miler Yanopoulos is now allegedly more than $2 million in debt. he owes hundreds of thousands of dollars in unpaid legal fees. He owes even more than that to investors at his various media properties that didn't work out. And he is in further debt to Cartier, the luxury jewelry company. Wow. It's bad for her.

That's what I have loved to say about this. It's bad for her. I don't know. I just kind of think, you know, there's the macro political picture, which you two so eloquently described. And then there's sort of the micro picture of what was Milo Yonopoulos past tense. Like, what was Milo Yanopoulos? To me, I don't see him as someone who ever really planned this out in a long game sort of way. I suppose if he had, he would just be doing something entirely different. But like even someone like Candice Owens, who I find to be like very, very. strategic, very savvy, always getting ahead of the next thing. Whereas, like, Milo strikes me as

someone who from the beginning was just always trying to string along one controversy to the next to sort of juice out one or two more years of relevance. And eventually, it just gave out under the weight of its own ridiculousness and sort of political stupidity. It was not sustainable. No. No. No. I don't think he ever really had, like, a grand. plan for where it was all going to go. And I don't know if Candace Owens has a grand plan, I'm almost too scared to ask. But Milo, this story is like depressing on an individual level. At a systemic level, it's just really dystopian.

Also depressing. Yeah. Matt, I think like in the next day or two, I'm just going to send you like a wellness check DM to say after, after imbibing all these glossy, photo essays and profiles of Milo. Are you holding up or is your brain just totally, you know, are you in a dark place yourself now from convening this, convening this conversation? I think I might lean into like these like loose fishnet tops and I don't know. I might throw a couple crucifixes in there. Why not? Kat and Matt, thank you so much for going down this road with me. What a journey we've been on. There's that saying of like Milo Yanopolis was a Harvard study.

and it has concluded, thank you for participating. I do feel like, I do feel like Milo Unopolis has decidedly ended. Whatever that was feels over. And with it, an era of U.S. politics by gone. And so I like to cover these things almost like historically. Because, I don't know, I think there's lessons to learn from it. If you're a gay guy, don't do this. That is a really good takeaway, honestly.

Do not do this. And Matt, I just want to say how honored I was by the invitation because I have enormous respect for you over your recognition of the humanity of Palestinians and the atrocities in Gaza. And I know you've taken some flak for it. And so I was very chuff to be invited on this particular podcast. So thank you. Oh, that's kind of you. And no, as far as I'm aware, everyone is only nice to me on the internet. Same.

Same. And I'd like to keep my very limited knowledge of what people say about me there. But you both do excellent work. Where can people find more of it? Well, I mentioned the podcast I co-host, know your enemy. You can listen to that wherever you listen to podcasts. And if you really were stirred by this, my contribution to this conversation, you can subscribe on our Patreon.

Patreon.com slash know your enemy. And I'm on Twitter at Matthew Sitman. And that's probably the best ways to follow what I'm doing. I recently started my own YouTube channel. You can find it at Kat Tembarge. It is going well. I am very grateful to all who have listened and subscribed. You can also read my newsletter, SpitfireNews.com. And you can find me on Instagram, Blue Sky, and a few other places at Katte. to barge. Thank you so much for listening to this episode. It's a long one. I don't even know why I say that anymore. They're all long ones. I know. I feel you, Matt. You either enjoy it or you don't listen to this podcast anymore. I don't know what to say. But I'm so appreciative, you know, I like, I like dipping my toes into gay hell. And this is gay hell. I'm glad that you take trips into it with me. I so appreciate you. I love you so much. And until next time, stay fruity.