The Big Flop - Weinergate: The Rise And Fall Of Anthony's Weiner with Alana Levinson and Dan O'Sullivan | 101

Episode Date: August 18, 2025

Anthony Weiner went from passionate congressional crusader to America's most infamous sexter faster than you can say ""Carlos Danger."" With a powerful wife, promising career, and path to the mayor's office, he had it all – until his compulsive need to share underwear pics cost him his marriage, freedom, and possibly the 2016 election. Alana Levinson and Dan O'Sullivan join Misha to scrutinize one of our bigger flops (pun intended.)Follow The Big Flop on the Wondery app or wherever you get your podcasts. You can listen to The Big Flop early and ad-free on Wondery+. Join Wondery+ in the Wondery app or on Apple Podcasts.Be the first to know about Wondery’s newest podcasts, curated recommendations, and more! Sign up now at https://wondery.fm/wonderynewsletterListen to The Big Flop on the Wondery App or wherever you get your podcasts. You can listen early and ad-free on Wondery+. Join Wondery+ in the Wondery App, Apple Podcasts or Spotify. Start your free trial by visiting wondery.com/links/the-big-flop/ now.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Picture this. You're lounging on your couch, ready to indulge in another hilariously disastrous episode of The Big Flop, but then, bam, an ad. Don't let that be you. With Wondery Plus, you can enjoy The Big Flop a whole week early and completely ad free. It's like having a fast pass to the front row of the VIP section. Upgrade your listening experience and join Wondery Plus in the Wondery app or in Apple Podcast. Your uninterrupted flop fix awaits. So some of y'all out there listening might be cursed with the last name that only a gym classful of 12-year-old boys could love. To make fun of. Like the last name, Weiner, as in disgraced Senator Anthony Weiner. You see, Weiner couldn't keep his Weiner in his pants.

which led to a fallout so horrendous, it not only affected his career, but basically the fate of the United States. So yeah, let's get into it, Besties. Please welcome former Congressman Anthony Weiner. Let's talk about the... Thank you very much. New revelations in the Anthony Weiner of Carlos Danger sexting scandal. Now getting the attention of federal prosecutors a subpoena just issued for the former congressman's cell phone record. Anthony Wiener has already lost so much his congressional seat, the chance to be New York City Mayor

and his wife. We are on a sinking ship. Navigating family matters can be tough. At Learners, we understand the challenges you face. Whether you need help drafting a pre-up, filing for divorce, or making

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wherever you get your podcasts. From Wondery and at Well Media, this is the big flop, where we chronicle the greatest flubs, fails, and blunders of all time. I'm your host, Misha Brown, social media superstar, so vote for Mish. Capish, at your bestie Misha. And y'all, I am so through. Because on the show today, we have pop culture writers and co-hosts of The Outfit. It's Alana Levinson and Dan O'Sullivan. Welcome to the show. Thanks for having us.

Oh, my God. What's been going on? What's coming up? What's new? We have a podcast premiering August 14th, anywhere you get your podcast, the outfit. We're talking about the mafia and how the mafia explains America. We have some incredible stories coming up, right, Alana? And a lot of big flops.

I mean, a lot of these mobsters are flopping their ones. way to jail. Tune in. Tune in. Yes, I can't wait to listen. Oh, thank you. So before we get into the topic of today, I'm just going to go straight in like an unsolicited dick pick.

What's the first political sex scandal that really stuck with you? I mean, you know, no pun intended, but the Bill Clinton, Monica Lewinsky thing, it was just all over the news when I was a kid and you learned a lot of stuff. from that, you know, I don't know, Alana, was there another one that comes to mind for you? That one, that immediately thought of that one. That sort of drowns out all the others, right? So formative.

I think I was in middle school. I think it was even earlier. Earlier, I think, yeah. Yeah, I think we're probably all around the same age. Yeah, yeah. 25. Yeah, right. Well, where to begin with Anthony Weiner,

the disgraced NYC congressman who had it all, a high-powered career, an influential wife, and a clear path to political stardom. Now, unfortunately, because of his predilection for getting up in people's DMs, Wiener's story gives rise and fall a whole new meaning. So let's go back. Anthony Wiener is born and raised in 1960s, Brooklyn. His mom is a public school math teacher and his father is a small-time lawyer. Weiner, like other local kids' age,

spends a lot of time bopping around St. Mark's Place in the East Village, watching movies with his friends, and rooting for the Mets. So he's not an exceptional student, by all accounts, but he goes to specialized high school Brooklyn Tech and then a respected state university, Sunni Plattsburgh, and that's where he becomes interested in politics when he runs for student government. Can you guess what his campaign slogan was?

Oh, boy. Something with Weiner. I mean, he has to lean into it, right? Like, he has to, this is the objection to overcome that his name is Weiner, right? Wiener's your dog? Something like that, you know. You're pretty close because he did use a pun that wasn't necessarily sexual. Vote for Weiner.

He'll be frank. Oh. That's a better second draft of mine. I feel like at some point later, before the sex scandal, he did make jokes about. Sure. the last name. And then when he was running for mayor, like, Weeners, cleaners. I don't know. He's like, I'm going to clean up the city, you know? It's like, okay. Unfortunately, he doesn't win in this race, but a kid who does get elected drops out, and then the president of the student

government has to pick somebody else. And the president actually doesn't want to pick him, but Weiner lobbies all the members of the student senate to get this appointment and they give it to him. What an inspiring story of democracy in action, right? And not to besmirch student government officials, but I already knew when you mentioned he was a Mets fan that he's a nerd also. So this is, I'm seeing the monster forming already, you know, from just this dark origin story. Yeah, it's sort of God loves a trier kind of energy. He never takes the L, which is like, do I respect that? Or is it really deeply sad?

I don't know. I don't know, but it's amazing. I know. It's a fine line. Now, I mean, it is clear that Weiner likes a fight. He's a good talker. He's even better at capitalizing on opportunities when they present themselves. And after college, in 1985, Weiner goes to work as a congressional aide for Chuck Schumer, who is a representative at the time. And Schumer is Weiner's first and only political mentor. Weiner quickly picks up that even though there are hundreds of members of Congress, there are only a handful that actually run things. So if he can figure out who's really in charge,

he might actually be able to move the needle on a national scale. And over his six years, as Schumer's aid, Weiner develops a reputation for being both scrappy and combative. And dare we say, dangerous. That'll come back later. That'll come back later. Stay tuned. So now, in 1992, after the New York City Council adds extra

seats. Weiner sees an opportunity to level up and hold office himself. And he wants to do good for his city, but his rivals have more name recognition. His slogan this time is much less cheeky than his college days. It's no promises, just hard work. No promises, just hard. What do we think of that? It's a little madmanish, like when they have the first poster and Don Draper tears it apart, I feel like. You know what I mean? Yeah. What's hard work? No one likes hard work. You know, um, sorry, that's my really good Don Graper. What? It's just like, I tried really hard. Sorry it didn't happen. What? Can you think of a better slogan for him? I would go the opposite. I would say, if you vote for me, your wildest fantasies will come true. Yeah. Like, just promise the moon.

Don't promise. No one likes hard work, you know? Say whatever you want, I'm going to get it for you. You can't keep a good weaner down. Was that it? You have that ready. You have that at the ready. Well, wouldn't people respect that? I think so. I think so.

Well, since Weiner is green, he doesn't have a lot of money, but being plucky is not enough to win, right? So he has an idea. And it's a sketchy one, okay? In the primary, someone anonymously drops leaflets around the predominantly white district he's running in. and the leaflets tie his main competitor to two prominent and controversial black leaders, the Reverend Jesse Jackson, and the city's first black mayor, David Dinkins.

Now, neither of these two men are especially popular in these predominantly white areas, and the smear tactic is what works, and Wiener's opponent loses the primary by less than 200 votes. So in turn, at age 27, Wiener becomes the youngest New York City councilman in history. That's really interesting history because I remember I was growing up on Long Island at that time and remember that that kind of really racist sort of politicking, we associate, or I tend to associate with one of the parties, but it can be a bipartisan issue that everyone agrees on, you know. Now, he does start to win people over, gaining a reputation as a true champion for the people and the city. He helps revive the struggling sheep's head bay neighborhood.

in Brooklyn by encouraging grocery stores to come back to the area. He fights for more public funding for parks and beaches. He investigates fatal stairway fires and gets the city to use safer paint in their housing projects. And he even starts a program for troubled teens who go around cleaning up graffiti. Alana, you remember the name of these cleaners, don't you? How could I forget? The weiner cleaners.

But I mean, those are good. don't see any red flags about him recruiting a bunch of teens to be his weiner cleaners. I don't see any, you know, issues there. But no, you're right. That's a little surprising to hear because I guess I always had an impression of him as being a bit of a lightweight when it came to actual, you know, political work. Maybe that's later. Like the food desert stuff with the grocery stores, that's what the current mayoral nominee is running in large part on, adding these city run grocery stores, right? Absolutely. So when Schumer then runs. for Senate in 1998, Wiener makes a grab for his old boss's seat in the house. Now, he's got more

experience now, and yet he still doesn't have the kind of financial backing his opponents are getting, but he runs a stellar grassroots campaign and having the newly minted Senator Schumer at his side doesn't hurt, and he ends up winning the seat. So out of the gate, Congressman Wiener is tagged as a rising star in the Democratic Party, and he quickly gets added to powerful committees and task forces, where he continues to bring that New York energy to stuffy procedural debates. Now, for the uninitiated New York energy just means you yell, because you care. Yeah, you're just slightly abusive, but for the cause. Yeah, all of your staff is going to quit.

You're going to have, like, the worst retention. I believe, I forget, but he had a very bad retention rate of his staffers. It's because he works, they always have the same excuse, too, It's like, I demand too much of myself and my staff. And it's like, probably you're yelling about your lunch, but, you know, whatever. Yeah. You know, what we see in these episodes all, like a lot of like problematic figures. So many of them, they abuse their staff because they say, well, I work just as hard.

You know, I work 23 hours a day, so you should too. It's so different when you're the boss, though. I know, exactly. You get to snap your finger. Like, all right, maybe that's working, but you're snapping your finger. and saying, fetch me a binder so I can throw it at you. It's like, okay, that's work, I guess. You go draft up my ideas. Right. Yeah, it's also like, yeah, you're working to elect yourself. Right. Cool. You should be working around the clock. Absolutely. And it's working for him, though,

because in Wiener's public and private life, the middle class Brooklyn kid just keeps moving up in the world. At a function with Hillary Clinton, one of her aides, Huma Aberdeen, catches his eye. Now, Abedine is a rising star, a big draw for Wiener, and he asks her out on a date. Abidine Demure says she's too busy because of her work schedule. So he very loudly asks Clinton, the newly elected senator of New York, to give Aberdeen a night off. Now, totally embarrassed. Huma declines for now.

Yeah. It's funny that that still didn't work. He's like, O'y, Clinton. Give her a night off. I want to take her out. She's like, don't. No, I would rather come to work. Unfortunately, this is the first but not the last time Weiner will leave Abidine totally embarrassed. We'll get into it. But in time, as he continues to navigate the New York political scene, he convinces Abid need to give him a shot. So he finally wears down Huma. And after eight years of flirting and courtship, he proposes and she accepts. They become Washington's it couple

it's a D.C. fairy tale, okay? And in the summer of 2010, they're married with Bill Clinton officiating. Wow. If that's not an omen that your marriage is maybe headed towards trouble, you know? Oh, that's so real. I am a little inspired that you can annoy a woman for eight years until she marries you. Like, that's... Just got to wear them down. That's that 90s romantic comedy sort of thing where it's like, if you just stalked the woman enough. It'll work out. There'll be a montage. It'll all, you know, end with Bill Clinton marrying you. I feel like, yes, that's a cute way that they spin it. But she was a big political player. And, like, the fact that she married him showed that she thought he was going to be the next

president. Like, I truly believe that she was like, I am going to be the next Hillary Clinton. And I'm going to pick my partner very wisely. Oh, sure. So let's take a look at their wedding photos. Can you describe the picture for the people who are listening only? I mean, she looks gorgeous, as usual, as she always does. But you know what's funny is, like, even before we knew about the sexual predator stuff, he really does look like one. And I don't know if we're projecting that back on, but it's like his hair and like the suit. The suit is like a men in black suit, right?

Yeah, it's a classic ought sort of, is it oversized? It looks too big. It's a little big. Yeah. It's a little big. But what about her dress? It seems like it's a sort of Western wedding dress, but maybe is including some elements of her Indian heritage with the beating. Yeah, she looks great.

He looks like a congressman named Wiener. That's what he looks like, right? I mean, he does look like he's just going to go do a filibuster. Accidents happen daily, but there's nothing routine about the damage they cause. The right personal injury lawyer understands the physical and emotional challenges. you face following an injury. While we can't take away your pain, learners' experience trial lawyers

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is famous for sun, sand, sea and sex. But lately, life on the coast has taken a strange turn. The town's mayor, a respected pillar of the community, has been arrested for corruption. His wife claims he's been bewitched by a beautiful clairvoyant. Then there's a mysterious phone calls that local people have been getting. I am the Archangel Michael. The whole town has been thrown into chaos. As the mayor is unable to carry out his duties, I would like to address.

address you all. Legal proceedings have been initiated. Join me, Anna Richardson and journalist Leo Sheik for The Mystic and the Mayor as we investigate a story of power, corruption and magic. Binge all episodes of The Mystic and the Mayor exclusively and ad free right now on Wondry Plus. Start your free trial in Apple Podcasts, Spotify or the Wondry app. With his wife, Aberdeen by his side and having powerful friends like the Clintons at his wings, Wiener gets a jolt of bravado, shall we say. Just two weeks after his wedding, when Republicans try to stop a bill that would provide health care to 9-11 first responders, a video of a very feisty weiner goes viral.

Let's watch a clip of how he became a national figure. It is a shame! A shame! If you believe this is a bad idea to provide health care, then vote no! But don't give me the cowardly view that, oh, if it was a different procedure. The gentleman will observe regular order and sit down. I will not. The gentleman will sit. The gentleman is correct in sitting.

That's a spicy wiener. Some jalapenos on there, you know. So I have a little slight insight into this. I was working in D.C. at that time. I remember I had an internship at a political news outlet, when that happened. And what I remember hearing about that time was Wiener had a reputation as being like a show horse, not a workhorse, as they say. Like he wasn't really in depth on the issues and he liked the PR. But that went viral. Like YouTube had really only started the year or two before that.

And so that was one of the first political things I remember going viral. So that was my one insight on that, that that, I think that this moment honestly destroyed him because he finally got the attention he wanted and it just absolutely went to his head, you know, at this point. Sure, sure. You know what I'm thinking, though, watching that is like, I think we could use a little bit of that today. Exactly. And that was, it would have been interesting had all, had this flop not flopped, you know, I do think that people really responded to that. Yeah. I mean, that's a winning strategy, as we know now. People love it when like the guys banging the gavel saying, order, order, and you're going anyway? You're like, not listening to that guy, you know? Yeah. Well,

thanks to his relatively young age, his penchant for making a scene and rapidly changing tech landscape, Wiener becomes one of the first politicians to effectively use social media. Come on, influencer era. And he tells a bar crowd in Manhattan, quote, I follow Twitter for the Tea Party and show up just to F with them. Oh, boy. He's going down a dark path here. Yeah, yeah. The second you bring up Twitter, I'm like, delete your account.

Yeah. He blows up on Twitter. This is so funny to me, with 45,000 followers by the spring of 2011. Yeah, that was blowing up back then. That was great. I mean, that was, who. That will become his Achilles heel or Achilles penis, you might say. Not only does Weiner have Ant,

in his pants when it comes to getting stuff done in Washington, he's got other things in his pants that he can't seem to keep to himself. On May 27th, 2011, less than a year after Weiner and Abedine's wedding, a picture of a crotch bulge appears on Weiner's official Twitter account. Would you like to see it? Yeah, we have to. Okay, just wanted some consent here. Yeah. I was trying to find it last night. All right, there we go. Okay, so there it is. Okay, bro. I mean, could be worse, could be worse. Looks like Haynes Boxer briefs.

I was a little surprised by that. That's what I clocked it as well. And that seems a little, I mean, that seems like something I would buy, not high-powered Anthony Weiner, you know? That's for losers like me. What is this guy doing with it, you know? I'm thinking politicians, they're just like us.

Yeah, yeah, for listeners only, he hangs to the left if you were wondering. I'm sorry, but did he put, like, an early, like, Instagram filter on this photo? It's giving Paris filter, whatever. Like, he's trying to be artsy. Yeah. Is he playing a song under it, too? Like, Time of Your Life by Green Day or something? You know.

Oh, that's ridiculous. So, now, the post is quickly taken down, but not before news outlets notice. And of course, the story and PIC go completely viral. Now, sidebar, there are a lot of pictures of Anthony's Weiner out there. They're usually aroused crotch shots. Now, we're not going to show every single one. If you've seen one, you've seen them all, right? But Weiner tries damage control and claims he's been hacked, of course. Spoiler, he has not been hacked. He tweeted a photo. he meant to text, but here is his post defending himself. Do you want to read his tweet for the audience?

Yeah, this is a throwback, okay? TiVo shot, FB, Facebook hacked. Is my blender going to attack me next? Hashtag the toaster is very loyal. This guy is such a nerd. And I love that Tivo and Facebook are brought up, just to really signify this is from May 20, 27th, 2011, you know.

Yeah. I don't even understand what he's saying. This is a different language. These are ancient texts. Ancient texts. Scribes, scrolls. And he's doing schick, right? Like, what is my blender going to attack me next? What's funny about it is I feel like when you are hacked, it's not them then posting, you know,

filtered bulge picks. That's not what they do when they hack you. They usually like just go on a tirade that is like the opposite of your politics. Yeah. Does that make sense? It's like they're not interested in that, the hackers. I feel like a hacker would be like, Democrats are lizard people, you know?

Exactly. And then they're like, what? Right. Yeah. Anthony Weiner said, he's a lizard person. And then, yeah, right. That's what I mean. Like, they're not interested in his weiner.

I'm wondering who the first person was that had this excuse. Was it him? Like, I don't know. There was probably someone else, but it's like. It was Abraham Lincoln. He had a carrier pigeon with a photo of his penis. And he said it was from the south, actually. It wasn't me.

That's hilarious. Well, Anthony does double down, calling reporters jackasses for even suggesting he do something so stupid. He even tells CNN that he's hired a law firm to investigate the matter. But just five days later, he holds a press conference. Let's watch a part of it. Over the past few years, I have engaged in several inappropriate conversations conducted over Twitter, Facebook, email, and occasionally on the phone with women I have met online. I've exchanged messages and photos of an explicit nature with about six women over the last three years. For the most part, these communications took place before my marriage, though some

have sadly took place after. To be clear, I have never met any of these women or had physical relationships at any time. Oh, that was really difficult. I got a feel for the guy, however arrogant he is to stand up there and say, I talked with a bunch of girls online. Like, you're a grownup, man. That's brutal to see, you know? Now, Wiener's justification is that he's addicted to the attention, very much like you are saying, Dan, you know. He's a little nerd. He's finally getting the attention that he so desperately wants. And he claims people online reach out to him to tell him he's awesome. Then they might flirt with him a little bit, yada, yada, yada. He's juggling multiple digital side pieces.

I mean, like, yeah, what do you think about that explanation? Would you reach out to Anthony Wiener because you saw him on the daily show and you were just floored by him? No, but do I doubt, I don't doubt though that there are people that do that. It doesn't really matter, though, because what it shows is a complete lack of impulse control. Like, if you need the attention that bad that you'll torpedo your professional career and your marriage, it's a way bigger, probably. than that, right? Yeah. You know, it's funny, because if this happened now, again, I do think he would be like,

I'm a sex addict, you know, I have a disease and I need help, which maybe he does later. But I don't think being addicted to attention is really a thing. So, I mean, Wiener, he says he's very, very sorry, but he does not resign. No, he's going to keep him job. And even though he's an elected official, most people are more concerned about what his actions will do to his wife's career. Being now, Secretary of State Clinton's most trusted advisor, Aberdeen is a well-respected and powerful fixture in Washington.

Even though it's been reported that Aberdeen experiences a good amount of discrimination, she's liked by politicians from both sides of the aisle, which makes her a valuable liaison. And meanwhile, Wiener, because of his actions and the unfortunate coincidence that his name is synonymous with male Janitalia, it's a complete laughingstock. Now, while her husband makes a mess of things back home, Abidine is Clinton's chief of staff

traveling the world with one of the world's most powerful women. And the non-stop barrage of dick jokes is literally hindering high-stakes diplomacy at this point. What do you think is worse? The cheating or the humiliation? Ask somebody who thinks that all politics at this level is inherently evil. I go back to Alana what you said,

that I can't imagine that there's not some sort of like, even from Huma Abidine's side, that she chose him because of status and power and the potential of where they could be in the future, not love and affection and joy, you know. Yeah, I mean, I see it's similar to Hillary, right, where it's like her choice to stay with him. There's a lot more that went into that choice than just, I love him so much. Similarly here, I think she thought he can rebound from this. She was probably counseled that he could.

And it's like, it's like, you know, I'm not saying that she didn't love him and the relationship. It wasn't a personal betrayal. I also see it. I would be like, this is a business deal we got going. We're going to, you, we had a deal. We're going to be present. I'm going to be the first lady. And you know, there's also that element.

Well, they had plans, though. They got out of it because in June, the New York Times reports that Aberdeen is pregnant. Oh, wow. Yeah. I mean, she convinces herself that Wiener didn't actually cheat because all of his indiscretions were online, not IRL. Now, abandoning her first and only love seems unthinkable, especially with a child on the way. But compromising her career also is impossible. So something's got to give.

The longer Wiener stays in the spotlight, the harder it is for Abedine to focus on her work. You know, for the greater good, Wiener needs to retreat. And then, a few days later, another photo leaks of Wiener. Let's take a look. Oh, man. That is not a watermark you ever want over a photo of you. You never want the TMZ watermark.

Yeah. Do you want to describe this one really quickly for the listeners? So this is Anthony Weiner in a... I'm going to guess it's the Congressional Gym locker room. Yep. I'm willing to bet. and he is

draped with just a towel around his midsection, shirtless. A TMZ watermark is covering most of his upper half. So I can't actually judge his definition and tone. But yeah, he's taking a photo. It looks like a Blackberry. Another sign of the Times.

And there you have it. Also, I just realize he's kind of grabbing his crotch. Okay, so that's a little more explicit. That's very right. Grabbing our crotch. And yes, TMZ confirms that the leaked photo were sexted from the House of Representatives, Jim. So, yeah.

Cornered now, Wiener holds another press conference, this time to announce his resignation. He claims his actions have created a distraction, too great for him to continue to do his job, and that he needs time away from work to heal his marriage with Aberdeen. So, I mean, is this the right move? Yeah.

I think so. I think so, too. I think everyone would say, you need to go underground a bit, Go out on the farm, don't talk to the media. Chop your penis off. Yeah. It's your man, Nick Cannon, and I'm here to bring you my new podcast, Nick Cannon at night.

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you've always wanted. Introducing get a grip. So, if you're done with holding back, this is your space. Listen wherever you get your podcasts. Aberdeen and Weiner, they enter therapy, and a few months later, their son is born, and for two years, the couple seems to be making progress, and Weiner stays out of the limelight. By 2013, Weiner feels like he's been a good boy for long enough, and it's time to redeem himself. So he suggests running for mayor of New York City again. And Aberdeen, she thinks this is a brilliant idea.

Surely two years is a long enough penance for accidentally tweeting a picture of your underwear, right? She will publicly say that she's forgiven him and that he's a great candidate. And this is probably the only way that he will be able to win, but Aberdeen, by doing so, she's risking a lot. Even her boss, Hillary Clinton,

tries to talk her out of endorsing wiener, but Aberdeen, she's in love and she's not going to listen to her mentor. If Hillary Clinton said, drop out. Okay, this is too bad an idea for me to endorse. I would be, I would really take it under advisement, you know? Yeah. Not to mention, all of this happens while a film crew follows Weiner and Aberdeen around documenting his redemption arc.

Yeah, it's kind of hard to feel bad for her now. Like, I'm just like, I actually do believe people can change, right? Like, let's say he came back and he actually had, you know, stop, like, had healed or whatever. But what I want to know is why is that never the case? It just is never that case with the public figure. Like, they're always like, I'm different now. Please forgive me. And you're like, okay, sure.

And then, you know, I mean, we'll see what happens. I think it's because, like, they can't, like, in order to do that, they would have to kind of go away maybe forever. Right? And give up this pursuit and, like, realize, oh, there's more to life than. attention and power and all that, and I'm going to go be with my family, not get a film crew to film my own destruction, which is about to happen. Yeah. Yeah. And, you know, his comeback, at first, it was going well. He does well in early polls. His campaign is flush with cash, and New Yorkers seem to be warming up to the idea of Mayor Weiner. He even promises,

if elected, to set up a single-payer health care system, aka a publicly funded option. In the city, as a pilot program to prove that it can work, but then a damning detail of Wiener's past suddenly pops up. TMZ, again, publishes screenshots of sexy conversations between Wiener and multiple women from 2012, and Wiener is forced to admit he sexted with as many as 10 women under an alias before and after he left Congress, which means before and after he begged his wife for forgiveness.

Now, I remember the name, one of the great names of U.S. political history. Please let us know what was his alias. Let's all say it in unison. Okay. Okay. Three, two, one. Carlos Danger. Oh, my God.

It's so good. It's really, it's just delicious. It's one of the best names ever. Mitt Romney's fake name on Twitter was Pierre Delecto, which I honestly also love, But he didn't put the work in like Carlos did. Obviously, nobody can let Carlos danger slide. And now the fact that he has a funny name is somehow overshadowed by a sillier name, which is funny. Now, the camera crew captures all of the marital betrayal and political meltdown in real time,

including the story of one woman who deliberately trolls Weiner for having sexed at her. Like, she appears on talk radio, is photographed for the press, and shows up to confront him in person. As a result, Wiener's campaign manager resigns. That's too hard of a job. And in September, when the primary results come in, Wiener earns less than 5% of the vote. Bill de Blasio wins the primary and then wins the mayorship. But, I mean, at least Wiener has the happy family to fall back on, though, right?

Oh, I'm sure it's really happy. I'm sure. She's thrilled. He's going to be around the house more. Yeah. That's, you know. Hooray. No, obviously that's a big no, because once again, Aberdeen is not only personally embarrassed as Wiener's life partner,

but she's now tarnished by association and her career is on the line. So she has to decide whether to stay or go. And her friends and associates think she needs to leave Wiener, but she does hesitate. Aberdeen reportedly does privately request a separation from Wiener in 2014, but they don't divorce and they don't even move out of the same house. They continue living together and co-parenting their son, so, you know, Seems like a marriage of convenience. And while Aberdeen helps Hillary Clinton mount her presidential campaign,

Wiener says he is happy to be a stay-at-home dad. Honestly, like at this point, who are you feeling worse for? I mean, this guy, the last thing he wants to be is a stay-at-home dad. He wants to be out there hitting the streets, you know, not watching Bluey. Honestly, if this happened today, he'd set up an only fans. You know? That'd be, that he wants the attention. Anthony, if you're randomly listening, you still have time. Yeah, it's still time.

You still have time. So, yeah, iced out of a career in politics, ashamed to have a social life, Weiner retreats into the corner of the internet that he's not supposed to go to. A month after Clinton wins the Democratic nomination for president of the United States, Weiner warns Abidine, who's now vice chair of Clinton's campaign that the New York Post is about to publish a photo of him and their son. And no, it's not them hanging out at a museum or a park, because believe it or not, we have not yet hit rock bottom. On August 29th, 2016, the Post reports that Anthony Wiener has been secretly texting with another woman, who, side note, happens to be a Trump-supporting Republican. Not a good look for his wife or her boss. Now, among their messages is a snapshot of his son,

except the child is not the point of the photo. The point of the photo is Wiener's grotch. To be clear, this isn't an exploitative or inappropriate photo of his kid. His son just kind of happens to crawl into the frame while his dad is chatting back and forth with this woman. It's basically like, look, here's a picture of my cute son, but, oops, made you look. Now you've seen me in my underwear. It's cringe on a million different levels. And when it leaks, strangers start calling child protective services on Wiener. Yikes.

Dad of the year material. This is, I mean, this is like, Lana, you alluded to this earlier. I mean, this is addiction in some form. right? He's a deeply sick person. Yeah. I mean... Yeah. It's a compulsion, for sure. Now, for his wife, Huma Aberdeen, this incident with her son is the absolute final straw. Weiner will later admit to his wife in therapy sessions that he wasn't just texting women. He was having real-life sex with them in their family home while she was away. Now, even though privately their marriage has essentially been a husk since

2011, Aberdeen announces in 2016 that she's decided to separate from Weiner and third gross him out of their apartment, but the scandal is about to blow up even bigger than either of them could possibly imagine. Like, realistically, let's pretend like you don't know what's about to happen. How much worse can things get for this guy? I mean, I don't recall anything happening in 2016 involving Hillary Clinton or the news. I imagine, you know, he's going to have to leave Brooklyn. That was tough. Yeah. So in September of 2016, just two months before the presidential election between Hillary Clinton and Donald Trump, the Daily Mail, publishes a story that Wiener may have sexted an underaged teen. Now, since the issue involves a minor, the FBI

seizes Wiener's laptop. This all happens in the midst of Clinton's email server controversy, you know, the but-her emails thing? Republicans are eager to comb through the laptops of anyone who might have anything on her. And what if there just happens to be something on Wiener's device? Two weeks, before the election in a bombshell decision, the director of the FBI, James Comey, announces that he's reopening the investigation into Clinton's emails because he's found classified information sent from Aberdeen to Clinton on Wiener's laptop. Here's Wiener talking about how it went down. They had my laptop. They had it for weeks and weeks and weeks. They knew that wasn't anything on it that was relevant to the campaign. That was relevant to the investigation. The prosecutors in

New York said, why are you guys just sitting on this? He's never. answered exactly why it was he held on to this so long until 10 days before the election. They had it weeks before. The inspector general that looked into this asked the same question. Yeah. People in the FBI, the FBI was pulling against Hillary Clinton and Giuliani was getting leaked all this information. They had it for a long time. Why did Comey wait till 10 days before to talk about it? Do we believe him on that? When is he telling the truth? I mean, this is probably what happens a lot of the time with guys like this, right? For a long time, I was an editor of a men's magazine and we sort of examined toxic masculinity and covered a lot of, you know,

disgrace male figures in the Me Too movement. And unfortunately, obviously this is anecdotal data, but I would say it's almost always worse than what we think it is. Like, oh, do I wish it was just like, oh, he sent his bulge in the gym shot, like I said, and then that was it. It's like normally something like that reveals such a deep sort of lack of judgment. that is often far worse. It's like the tip of the iceberg.

Yeah, yeah. If you're that sick, crazy, whatever, that you would send that pick like from the Senate gym, it calls into what else are you willing to do? You know? Yeah.

Where does it stop? Well, but it does turn out that Weiner's laptop doesn't hold any incriminating evidence against candidate Clinton, uh, but the damage nevertheless was done. Clinton is dragged through the mud one last time.

She's shady, corrupt, under investigation. and Trump supporters gleefully chant, lock her up. Trump, spoiler, wins the 2016 election, arguably in large part because of this specific controversy. And from that point forward, historians will always wonder what could have been if Weiner had just kept it in his pants. Man, one of those inflection points, like in history, you know,

Lincoln gets shot, you know, and we don't get reconstruction. Anthony Weiner photographs his penis the last time, you know, know. And I don't know. That's a bummer. The Clinton campaign blamed a lot of different people for the reasons why she lost. I mean, this is obviously a very kind of legit one, although I do think there were many, many reasons. But I do think also, though, if Huma had dumped his ass when he did this the first time, then that also wouldn't have happened. You know, it's kind of, it's kind of an ultimate fuck around and find out. It's like, give him another chance. But, you know, down the line,

he might do something and then completely undermine your life's work, your boss's life's work. Yeah, literally. So in the fall of 2017, Weiner waives his right to a trial and pleads guilty to transferring obscene material to a minor. And he's sentenced to 21 months in prison. In 2020, Weiner is released from prison into a halfway house and is then forced to register as a sex offender. His first job out of prison is running a company where ex-convicts build countertops out of recycled glass. And when that company turns into a co-op and no longer needs a CEO, he gets a gig as the token lefty on a conservative talk radio station. He tries to rebuild his life, claiming that now, since he's been in prison, he's finally and truly learned his lesson. Weiner openly discusses his chaotic political history and his battle with sex addiction, saying he's,

he's in recovery. Some people want to believe him. Many refuse to trust him. I mean, after all, Abidine made the mistake a gazillion times, and it did not work out well for her. So, let's do a little where are they now? In late 2024, Wiener, now 60 years old, made a shocking announcement. After publicly claiming he'd never do it again, he did it again, he ran for office, entering the primary for his New York City Council District. Now, although Huma was not involved, she was apparently supportive, supposedly telling her ex-husband,

quote, this is kind of what you were born to do. God, the eye roll. Dude, she's so down bad. She's so down bad years later. Sick. It's sick. I think, obviously he's a sex addict. I think his primary addiction is to running for all. office. Like, that is what he needs to be working on. You cannot stop running for office no matter how

many times your penis gets telegraphed to the world. Why don't you, I don't know, go become like a sex addiction advocate or like, I don't know, do some community work that doesn't involve you being the face. Right. Now, in the primary election on Tuesday, June 25th, Anthony Wiener lost by a landslide. Huma Abidine published a tell-all book in 2021, where she finally discussed what it was like to live through Wienergate while juggling her high-stakes job and new motherhood. She still works for Hillary Clinton, who's a prominent public figure, obviously. And Abidine hangs out with celebrity activists like Amal Clooney. Since her divorce from Wiener, her love life has rebounded, she briefly dated actor Bradley Cooper

and is now married to Alexander Soros, son of George Soros. And the conspiracy theories will end there. No more right-wing. paranoia, right? Totally normal situation. So here on the big flop, we try to be positive people and end on a high. So are there any silver linings that you can think of that came about from Anthony Wiener? I would have to say, you know, I think Buddhism would teach us, right, that losing everything is the path to enlightenment, you know? All these worldly pleasures and desires. And if it is not sinking into his head now that he has lost everything, nothing will do it. My hope is that now, after losing however many times, having however many scandals,

he actually has a chance to stop messing around and just go be a dad somewhere, you know, and get some help, you know. But the rest of us are screwed, unfortunately. A lot of any silver linings? I don't know. I mean, I think it taught me. This story teaches me, if you don't deal with your personal problems, they're coming out. And they're going to... And it's going to hurt Hillary Clinton. Yeah, exactly. Exactly.

You know, for me, I was thinking the silver lining is it was just really nice to remember that Twitter used to be kind of fun. Yeah. Misha, that's so real. And 40,000 followers was like, you were doing good. He blew up. So now that you both know about the rise and fall of Anthony's weiner, would you consider this a baby flop?

a big flop or a mega flop. I mean, I have to go there and say, given the domino effects that happens from one man's perpetual horniness, possibly leading to us electing American Hitler, this is a mega flop. It's insanely mega. For what it is,

it is remarkable that it could have this effect. A butterfly lands here, a tropical storm goes there, you know? Also, we just have to say, like, the amount of chances, he got that so many other people from different backgrounds, uh, races, gender would not have gone. It's like, I still can't believe it. Well, thank you so much to our guest, Alana Levinson and Dan O'Sullivan, for joining us

here on The Big Flop. And of course, thanks to all of you for listening and watching. If you're enjoying the show, please leave us a rating and review or subscribe. We'll be back next week with another flop. They were a group of privileged L-18 to desperately needed a hobby. What they choose? Robbing the homes of celebs. Hold on to your wallets because we're talking the bling ring. Bye. Bye. Bye. members can listen ad-free on Amazon Music. Before you go, tell us about yourself by filling out a short survey at Wondery.com slash survey. The Big Flop is a production of Wondery and At Will Media, hosted by Misha Brown, produced by

Sequoia Thomas, Harry Huggins, and Tina Turner, written by Anna Rubinova and Luke Burns, engineered by Zach Capone, with support from Andrew Holtzberger. The video podcast is edited by Olivia Vessel. Managing producer is Molly Getman. Executive producers are Kate Walsh and Will Mnati for At Will Media. Legal support by Carolyn Levin of Miller, Korsenik, Summers, and Raymond. Senior producers for Wondery are Adam Azaraph, Matt Beagle, and Jennifer Klein Walker. Managing producer is Sarah Mathis, and the senior managing producer is Callum Pluze.

supervisor is Scott Velasquez for Friesong Sink. Theme song is Sinking Ship by Cake. Executive producers are Lizzie Bassett, Dave Easton, and Marshall Louis for Wondering. Report suggests that Canadian taste buds are bored to tears. My mouse can't handle another dull drink. Summertime smoothie experts everywhere are recommending a watermelon wake-up from booster juice. It's so smooth, cool, and refreshing. And ridiculously delicious. Enjoy the watermelon wave and watermelon explosion smoothies available all summer long at a booster juice near you.

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