What A Day - Donald Trump Dreams of Empire

Episode Date: August 31, 2026

In case you missed it, President Donald Trump announced a deal that would give the United States a stake in Venezuela’s vast oil reserves on Friday. And over the weekend, the United States and Iran exchanged fire for the first time in a month. The Bulwark’s Tim Miller joins What A Day host Jane Coaston to break down Trump’s increasingly imperial adventures! Jane and Tim also take a moment to say goodbye to a right-wing activist who cheered on deportations and then got himself deported.Show Notes: Check out Tim's podcast – tinyurl.com/yzx2wv22 Call Congress – 202-224-3121 Subscribe to the What A Day Newsletter – https://tinyurl.com/y4y2e9jy What A Day – YouTube – https://www.youtube.com/@whatadaypodcast Follow us on Instagram – https://www.instagram.com/crookedmedia/ For a transcript of this episode, please email [e-mail]

Pete Hegseth is very insecure in his role because he's unqualified for it. He knows it. And he likes people telling him he's doing a great job. He's just like a little boy out on the soccer field, turning to see if dad noticed the last shot that he took on goal. It's just he's a child that needs constant care and tending and puffing of his. A little ego. It's Monday, August 31st. I'm Jane Koston, and this is Whataday.

We're going to be diving deeper into the news each day with our guests. Today I'm talking with the bulwarks Tim Miller about President Donald Trump's imperial ambitions and some of his biggest fans. Tim, welcome back to What Today. What's up, girl? Happy to be here. So, Tim, let's start with Iran over the weekend, the U.S. How are things going? See, the thing about this is that we keep being told that, like, the mission has been accomplished.

Literally, Trump said that last week. The mission is accomplished. But over the weekend, the U.S. and Iran exchanged fire for the first time in a month. U.S. Central Command, I am seeing here, said it struck Iranian launchers after observing forces with Iran's Revolutionary Guard Corps, preparing to launch rockets with sea mines into the Strait of Hormuz. Sure. What's going on here? Like, this is the war that never ends. And it's interesting that there seems to be.

no real desire to wrap it up, just a desire to tell us all that it's wrapped up. Yeah, well, a couple of thoughts. On that part, on the propaganda part, I get a kick. It was a nice flashback to the spring when Axios was reporting, you know, every week that a ceasefire was near, that we had won, that the Iranians were ready to fold, according to their sources, Jared Kushner, inside the administration and outside in that case. And we had a little reprise of that last week where I believe it was on Thursday, the headline from Axios was, quote, that sucks. is open. U.S. gains the upper hand in battle for Hormuz, and then like 36 hours later,

we're bombing an island in the Strait of Hormuz, because that's how you know that things are open when you've got to just keep bombing, to keep them open. And that's very, very typical of other things like that in your life. So a lot of this is propaganda. Trump doesn't really care about the facts. He cares about what people think. But wars are different than, you know, lying about elections, right? Like you can see the actual results. in a tangible way. And I think the other, like, I wouldn't say more generous, but I think the other way, the reason why this is dragging on is because Trump doesn't

want to escalate. He doesn't want to just tucktail. And so I think that the option that he's been provided is we're going to try to create as much economic pain on Iran as possible and, like, hope that there is some internal, you know, issue within the Iranian leadership and that they, you know, protests come back up or they decide that they need to come back to the table because they're feeling so much pain. I don't see that happening. No.

I think that's the current thinking. Yeah. And I think it really goes to a lack of understanding from Trump and everyone around him about the Iranian regime, which is funny because we have been told for last 40 plus years that the Iranian regime is unreasonable, that they are hardliners. that they will never give in, that they, you know, they've responded to multiple decades of sanctions by not changing anything and continue to execute protesters. They've even been executing protesters at a more rapid rate. And the idea that, oh, we'll just put extra economic sanctions on them.

And now they'll do what we want, especially after you have a new Ayatollah who has witnessed the death of his father and multiple members of his family as a result of U.S. Israeli, irstrikes. Like, it doesn't, I mean, none of this has ever made sense, but it makes less sense now. I mean, there's that saying about war that in a war, the opponent gets to have a say. And this is a moment, like, why would Iran give in now? Why would they? What is their motivation? What's the point here? Yeah. I think the theory of the case of the administration is that they can be so crippled economically. They have no choice, especially with the blockade on oil, but it's just, it's hard to believe that, especially with now, I believe it's this week, where, you know, the Iranian prime minister is meeting with Putin and Kyrgyzstan, the Chinese

that are there for, you know, a summit. This is kind of like a, you know, kind of Austin Powers, Dr. Evil Summit and Kyrgyzstan. And I don't, you know, they're going to get support from these other countries that want to help them continue to weaken us. And they're succeeding. and continuing to weaken us. I mean, just last week in the Washington Post, think about how shocking this is. There was a memo that was leaked that had the leaders of the Air Force Army and Navy

and additional four-star commandants saying, we're in real danger here if we have to keep this level of troops and keep spending this amount of munitions in the region because it means we're going to not, you know, be prepared to deal with things in other parts of the world or here at home. And so if that leak is coming out of the Department of War, you know, they can read the newspaper in Iran.

Like, you might say it they're in caves, but let me tell you it, they can read the newspaper. Like, this is not, you know, all the things the administration is saying about the Iranian regime is not been true. And so they know that Trump is facing pressure. So why would they fold? You know, it's a match of chicken. They're looking across at Trump and being like, this guy's going to be the one that folds. Right. Exactly.

Because it's not like, you know, they're not really. worried about a midterm election exactly. Like, they don't care. And so Treasury Secretary Scott Besson is hosting meetings of the G20 finance ministers in North Carolina today and tomorrow. As Washington wants to make other countries pressure, Iran and economically isolate them, two weeks ago, the UAE is suspended all trade with Iran after saying he had come under fire from Iran. So, like, Iran is very economically isolated, but also Iran has been economically isolated for a pretty long. time. And now that you have, as you mentioned, you have China, Russia and India all meeting together in Kurdistan and Putin having talks with the Iranian president. It seems as if this is driving

Iran towards our enemies, even while being at war with us. It doesn't make sense. But also something else that doesn't make sense. Do you remember Venezuela? Oh yeah, that's a country that in Central America, believe we did a coup there. Yeah, I believe that there was something about democracy. I seem to remember that very vaguely. It was like, you know, the beginning of January. We had all just come off a Christmas break. A lot of it happened.

But on Friday, the Trump administration dropped a plan to develop a vast amount of Venezuelan oil reserves through a deal with a private Venezuelan company that is controlled by an ally of Venezuelan president, unelected president and Maduro ally, Dulcea Rodriguez. The U.S. will take a 35% stake in that company, and the U.S. would get 55% of this oil. Trump called it the, quote, biggest oil deal in the world, which, sure, per NPR's reporting, this is not going to do very much for U.S. oil prices. The larger oil fields involved in the deal aren't developed, and that would take a really long time. And I presume the next administration, hopefully a Democratic administration would say absolutely not. we want nothing to do with any of this. But it's interesting how we were talking beforehand about like Trump's clearly imperial ambitions where it's just like, we'll just take it. Like we don't care who runs Venezuela. We pretended to care. We said nice things about your

Nobel Prize winner, but we don't care about that. We just want your oil, which we can't even really use. Yeah. Just to self-cruction, Venezuela is famously in South America. We're doing coups everywhere. We're cooing. In the Americas. So it's like getting them mixed up in my head. But look, there are a lot of ways to critique what we're doing in Venezuela. There's the imperialist angle as you laid out. I think that there are kind of unpredictable consequences to that. You know, like the Venezuelan people are not going to be so thrilled, I don't think, that we're coming in, doing a coup, and then raping their natural resources and taking them for ourselves. Like, you know, allegedly, when all of this nonsense started, one of the, you know, fake reasons for our actions in the Caribbean and Venezuela is that we were worried about Trenda Aragua was one of the reasons where we had the jail.

Wow, that's a callback to January this year. But it's like, okay, so if we're so scared about the Trenda Aragua gang that has infiltrated the country, it just seems like a risk that there might be some backlash with Trendaarauga now that we've done a coup in their country and we're stealing their country. oil. So there's that. I mean, there's obviously the principle of this. There's the fact that this is a socialist plot with like a corrupt Venezuelan oligarch. Yep. It also goes against, I mean, I know we don't care, but it strictly goes against the Venezuelan constitution. It does go against Venezuelan constitution. So did the coup, by the way. But I just, you know, this game is kind of silly at some point, but like imagine if Barack Obama had done like a coup in a foreign country, then did a deal with a socialist communist dictator and had their buddy, like, sign us up to

to be a state-run enterprise along with the socialist leader of this country and their friend. I mean, you know, you could not, like, douse the fire that Fox News, you know, the flames that would be, you know, blowing off of the Fox News headquarters on the Avenue of the Americas. I mean, there'd be no amount of firefighting that could stop it. They would be, they're so pretend outraged about that. Or who knows whether outrage. But there's just nothing about this. Like there's no, it is not right morally.

The principle is not right. And it's probably also just not going to happen. No. Like to your point that it's like, okay, this is going to take a while. It's like, all right, is the next American administration, as Delcy Rodriguez really that secure of a leader in Venezuela? Is the next leader of Venezuela really going to be thrilled to give away 35? percent of their oil to America? I don't really believe so. I don't see that happening.

Yeah. The Wall Street Journal said, quote, the U.S. government is essentially getting in bed with a foreign dictator and her favored capitalist, which like, yeah, that seems to be happening. But you made a point about people being fake outraged. And there's a group of people online who are often fake outraged on behalf of the Trump administration. And I mean that, like, literally on behalf of the Trump administration. Because, um, You and I spend a lot of time on the internet. We should stop. We should really stop.

And there have been a host of like online right wing influencers who have been around for a long time and who have always been like woo-woo, woo-woo military, woo-woo. If you're a Democrat, you're obviously an evil troupeater. Woo-woo-woo. Pete Higseth is so great and cool and handsome. And it turns out that a host of them, as revealed by the Washington Post on Sunday, are literally being paid by the Pentagon. According to reporter Dan Lamoth,

the Pentagon has hired multiple conservative veterans with big followings on Twitter as special government employees or my favorite, highly qualified experts. I wanted to ask you, what does the Pentagon think that this is going to do for them? I think that Pete Hegseth is very insecure in his role because he's unqualified for it.

He knows it. and he likes people telling him he's doing a great job. You know, he's just like a little boy out on the soccer field, turning to see if dad noticed the last shot that he took on goal. Right? It's just he's a child that needs constant care and tending and puffing of his little ego. And so I think that mostly this is that, like the team that monitors the Internet

inside the Department of War can send reports to Pete and be like, look at the engagement we've had for the compliments that you've received online. So I think that is a big part of it. I don't know that there's really that much of a strategic objective beyond that. I think it's a pretty good deal to get taxpayer dollars to tweet about how great the Secretary of Defense is, if you're one of these guys. I mean, Kurt Schlichter, for one example, is somebody that I've dealt with online for a long time. He was very obsessed. I was talking about. I was talking about. I was talking about how the number number number trumpers are cucks and have been cuckolded and how people with big penises are sleeping with our wives and i don't know um he just he's thought a lot about

other people's penises and he's tweeted at me about other people's penises quite a lot which says to me something about what's happening in his own home but uh that's neither here or there i'm not really thrilled about the fact that like this man is now being paid by me yep it's like armin it's like he's being paid by me to tweet ahoy at people which is a very insular national review related remark, which I think that gets to something I keep thinking about, which like, you're paying conservative influencers to tweet about you on a platform owned by Elon Musk, which is kind of like, it's like influencing to the already heavily influenced. Like if you were trying to like change hearts and minds or get more people to be supportive of the Pentagon,

like, why would you do it there? Unless all this really is is so Pete Hegseth can see it. I think it goes to like so many members of this administration demand to be high on their own supply. Yeah, there's one other thing that they are doing that may be having some influence is that Pete Hagsuthy's using it to go after the people that are, that make him insecure in his job within the administration, like the Army Secretary Dan Driscoll. And like you've seen, if you kind of look at the paid accounts, you notice a lot of them went after Dan Driscoll, who was kind of more and if you will, like the Vance camp of the internal feuding within the administration on foreign policy matters. And so Pete is like using our

money to pay people to like go after, you know, his own personal foils within the administration, which, you know, it's a nice deal if you can get it. He also might think he's running for president. So there's like a little bit of laying the groundwork for that using our money to help the draft Pete Heggseth, 2028 campaign. It's pretty outrageous, really. And they did it in secret is the other thing. Like this was leaked. And my colleague Will Summer, I kind of noticed that this was happening a little bit just based on this spat that's too complicated to explain that burst out into the scene online. And then, you know, over at the Washington Post, they did additional investigating on that

and found that the program was like much wider than we had thought. We'll get back to my conversation with Tim Miller in a moment. You follow the news every day. Now put it to work. Running mate is the all-in-one organizing platform that lets anyone run a real field program. voter data, canvassing, phone banking, and goal tracking all in one place. No operative experience required. Whether it's a local race, grassroots cause, or a registration drive, Running Mate gives you everything you need to run it in one accessible, affordable platform.

Built for organizers, buy organizers. Try the free simulator at running mate.comate.io slash day. That's running mate, one word, dotio slash day. What a day is brought to you by dose. The most underrated organ in your body? Your liver. It's doing 500 plus functions every single day, filtering unwanted elements, supporting digestion, helping with energy, but we never think about it until there's something wrong.

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placebo-controlled studies showing its positive impact on liver enzyme levels. Ready to give your liver the support it deserves? Head to dosedaily.co slash wad or enter code wad to get 35% off your first subscription. Your body does so much for you. Let's do something for it. That's D-O-S-E-D-A-I-L-Y dot CO slash Wad for 35% off your first month's subscription. Let's get back to my conversation with Tim Miller. I want to go back to the draft Pete Hegsaf thing because I'm kind of, so Hegseth has denied any interest in running for president. But he went to Iowa. Yeah, he went to Iowa during a war to campaign for somebody else, you know, like defense secretaries do.

But I had to ask you, have you ever seen someone who is a prominent part of an administration with a third. 32% approval rating think, I should run for president. Like, I went back. Back in 2008, you have one person who is a member of the Bush administration, the George W. Bush administration, who even attempts to run for president, that's Tommy Thompson. And he hadn't served in the Bush administration since 2004. And he dropped out before the primaries. Like, why?

Why would you think you have the juice? John Ashcroft wasn't in there, you know? Weirdly, John Ashcroft did not try to run for president. You'd think that the, you know, I covered up a nude statue thing would have done really well in New Hampshire. But like, how much juice does he think he has? It's a different world. I mean, it's funny to like think about this. For any listeners or viewers who came to politics in the Trump era because of the horrors and don't remember the things before, you might be surprised to learn that when Hillary decided to run in 2016, she had like a 70% approval rating at the same.

State Department. She was very popular as the lead diplomat of the country. And then, you know, kind of things went poorly after that. Most people remember how that ended. But like, Hague Seth is starting from such a lower baseline. Obviously, the thing is the juice. I think the reality is that all of these guys, back to your only comment, are high on their own supply. They're like, if Trump can do it, why not me? And I think that if you're Hague Seth, I don't know. You look around. You like, sure, you have a low approval rating, but who are you scared of? J.D. Van Mr. Charisma. And I think that someone is going to have to run in the more, you know, kind of muscular,

military, we do TRT and do push-ups, Lane in the Republican primary. Why not Pete? So one right-wing influencer, we have lost over the weekend because he's been deported, is at Milo Unopolis. I wish you would have warned me about this. I would have brought my 40, you'd have poured one out for Milo. I could play the song from the seventh Fast and Furious movie. We will see you again, Milo Unopoulos.

We won't and we will not miss you. So if you were online around the 2016 election or ever, Mila was kind of inescapable as being, he went on a college tour that was entitled, and I quote, the dangerous faggotte tour. He was among the, I'm just going to go to college campuses, say things that are purposely going to make people mad and then complain when people get mad at me

because I am now a victim. And then he said a bunch of stuff that it turns out even the people at the conservative political action conference was like, okay, that's enough. Then he worked for Kanye. He was hanging around with Marjorie Taylor Green. That's how Laura Lumer,

this is a cursed series of words, by the way. All of these words are not in the Bible. Laura Lumer is claiming credit for getting him deported. And she's a terrible. person, but Milo is also a terrible person and also somebody who was a giant enthusiast of mass deportations. He said, quote, we, including him, who is not an American, as we know, have got to deport millions and millions and millions of people, basically adding like nothing else matters but doing so. But he did not mean himself. He told Joe Rogan in 2016, quote, I mean bad immigrants, adding, quote, I don't mean handsome, charming, successful, blonde-haired British.

immigrants. Should I feel... Not a natural blonde. No. Should I feel bad? Many things to object to there, but... No. Should I feel bad for him at all? Because I don't.

No. You should not feel bad for him. I mean, he posted also once, I thought you were going to read about this, about how asking whether it was appropriate to masturbate while watching ICE detentions because they give him so much joy to watch people be detained that it got him horny. And so I've got to tell you, I am taking immense pleasure. not to that degree, and Milo's deportation. And I feel no guilt about it at all or no sadness. And every once in a while, people get things right. You know, broken clock is correct twice a day. Maybe

that's true on the deportations. And look, these guys are all hypocrites. It's important for people who are on the right, I think, to see what's happening, right? Like the people are being deported who are not violent criminals, whatever you say about Milo. He's a lot of bad things, but like... Immoral. Terrible person. Right, but it's not like... We might consider him to do the worst of the worst for his ideology,

but not in the sense of, oh, we're going to deport the drug dealers and the criminals that people bring fentanyl in. Like, that's not him. So I think it's important for people to see it. And I don't know. The worst part about the whole story is that Laura Lumer gets credit for it. Because I got to tell you, I was there for maybe about the origin of their feud because Lumer and Milo had been close friends.

And then they got into a few. you'd basically, like everything else over on the right these days, over Israel. Like on the left, for that matter, where Laura, you know, Milo was kind of siding with the anti-Israel, right-wing kind of Tucker crowd. And I was, I famously was at a bar in Arizona at a mega cocktail hour of some kind. And Carrie Lake came up to me, accosted me, and got right in my face. It looks like she might be right to hit me. And Laura Loomer was the peacemaker. intervened and told Carrie to calm down. And I asked her why she did that.

And she said, I've got a bone to pick with a different homosexual at this party. And then proceeded to sprint over to Milo and start screaming in his face. And then they got into a fight. So, you know, that's what happens when you go to MAGA, you know, drinking events. These people have the control of the federal government. Seriously. Complete control. Complete control.

the federal government. They're deporting people based on like internal feuds. Yep. Right? And it's like honestly. It's like if you put Cartman in charge of the deportation, and he's like, I want to get Kyle out of the country.

Like that's what that is basically the equivalent of what's happening in the government. I'm stealing this, but someone joked that this is like the night of the long knives, but if it took part in like the parking lot of a Walmart, I want to end on something very important to me personally. Great. Which is that Republicans don't know ball. They do not. So over the weekend, Democratic Michigan Senate candidate, Abdul Al-Said, was on television, as he is. And he talked about how he was looking forward to college football season. And he mentioned the phrase, he's a Michigan graduate, a Michigan man, as we call them, beat Ohio. And then went on to talk about Ohio, J.D. Vance, did attend Ohio State University. And a bunch of right-wing.

influencers decided that Abdul is the stupidest person in the history of time because they don't know the Michigan Ohio State rivalry in which Michigan has been calling Ohio State Ohio for like a long time. Like beat Ohio is like a thing that we've been saying for maybe like 15, 20 years. It's like a pejorative. It's kind of like the madman. It's like I don't think about you at all. No, no. It's kind of like this is a rivalry.

I can't even dignify you by getting me. No, no. Why would I say all of those words? Why would I do the whole the thing? No, I'm not doing that. But what struck me was like Ted Cruz and a host of other like. Like the RNC account. The R&C.

Like a million people. Mary Catherine Ham like mainst like Fox commentators, a bunch of people in a very smug way. Yeah. Like, oh, how could he not know that it's Ohio State? And then my favorite part of this is all the replies of just being like, you dipshits. Like you absolute idiots. And I think that it goes to like the. you know, the upper echelon of the American right has long purported to have like this,

like, deep tether to American culture and they understand America. But like, they're as, you know, siloed and elitist as anybody else is. And so all of their understanding of college football is generally like they've kind of gotten some like SEC something, something, something, because they spend a lot of time on the internet. But like when it comes to real deal college football rivalries or talking about the sport in a way that isn't supposed to just, I don't know, infuriate people or punish minorities, they can't do it. Like they have no idea.

They don't, you know, they don't know ball. And it, it upsets me personally. They don't know ball. This is a big Pablo Torre thing as well. Trump doesn't know ball. He pretends to. He goes to all the sporting events. But like his knowledge is stuck in like 1987.

Right. And he last actually paid attention. And by the way, that's fine. If you're a viewer and you don't pay attention to sports, nothing wrong with that. Yeah. What is upsetting? And what was driving me crazy. is that all of these like MAGA influencers and up to including Ted Cruz were like posting

about this in the most condescending matter to Abdul, like the brown guy doesn't know anything about football like I do. I'm a real American and this guy showed that he's an idiot. And meanwhile, they were wrong. Yeah. And like none of them to my eye like changed it, updated to be like, oh, you know what? Hey, we didn't realize that. I'm more of a Georgia fan.

I'm more of a Texas fan. I didn't know the intricacies of the rivalry and the insults. That's allowed. You don't have to know exactly what insult USC calls UCLA. I don't purport to know that. I'm familiar with the LSU Alabama rivalry. I've got my Get the Nat t-shirt on right now. Well, I'm taping this.

Get the Nat. And people watching this don't even know it Get the Nat references. And good for you for not knowing. But the like just stupid, condescending, I'm a real American, you're not. It is off-putting, has a hint of racism, but it also kind of makes me happy that they showed their ass that badly. I know.

Because they don't know ball. I know. Mary Catherine Ham did say, like, you know, this is a blind spot for me. I pay attention to SEC Georgia football. And I'm like, sure. But also, I am going to send you like 97 videos of people chanting beat Ohio at various sporting events. I will do that. That is my right.

That is deserved. And you well should. Tim, as always, thank you so much for joining me. Thank you, Jane. We'll see you soon. That was my conversation with Tim Miller, host of the Bullwork podcast. That's all for today. If you like the show, make sure to subscribe, leave a review, tell Todd Blanche to get a hobby and tell your friends to listen. And if you're into reading, and not just about how the Attorney General has issued a new subpoena in the long, long, long Trump administration effort to get former FBI director James Comey,

What Today is also a daily newsletter. Check it out and subscribe at crooked.com slash subscribe. I'm Jane Koston and Todd Blanche. Join a run club. Take up pottery. Try Krav Maga. What Today is a production of Crooked Media. Our show is produced by Caitlin Plummer, Emily Forer, Erica Morrison, and Adrian Hill.

Our team includes Haley Jones, Greg Walters, Matt Berg, Joseph Dutra, Johanna Case, and Desmond Taylor. Our music is by Kyle Murdoch and Jordan Cantor. We had helped today from the Associated Press. Our production staff is proudly unionized with the Writers Guild of America East.