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Susan Glasser: Trump Has a Man Problem artwork

Susan Glasser: Trump Has a Man Problem

The Bulwark Daily

October 8, 2026

The king of the birther conspiracy knows he needs to round up the white male vote, so he's serving up one of his old faves—straight-up anti-Muslim bigotry. And he's added a new one: Making Americans pay for another political ad, this time about what a tough guy he is.

Speakers Tim Miller, Susan Glasser, Alyssa Slotkin, Marco Rubio, Mike Rogers

TopicsPoliticsNewsSociety & Culture

Tim Miller (0:13)

Hello, and welcome to The Bulwark Daily. I'm your host, Tim Miller. Delighted to welcome back to the show, 20th time, a gold jacket guest, staff writer at The New Yorker, co-host of its Political Scene podcast. Her most recent book is The Divider.

It's Susan Glasser. What's up?

Susan Glasser (0:28)

Wow, I want a gold watch or something. That's amazing.

Tim Miller (0:32)

We're working on it. I need a 25 guest appearance present. I'm on it.

Susan Glasser (0:39)

I can hardly wait.

Tim Miller (0:40)

2027 It'll happen in 2027 We'll come up with something. I've got some great news for you. I do think an article this morning from The Wall Street Journal is a little bit of a preview, that the best is yet to come when it comes to hilarious stories of Trump friends shivving each other in the news.

And this one is Kimberly Guilfoyle, former partner to Don Trump Jr, former romantic partner. She was preparing for a congressional hearing to become US Ambassador to Greece, was going through her finances, realized she had some problems. So she texted a Trump donor saying she needed $100,000 sent to her American Express in a way that wouldn't leave a paper trail. Honey, please, I need you to get this done for me today. Prayer hands emoji, she sent to Eric Dieters, former congressional candidate and Trump donor. She asked him to draft a letter saying he owed her $250,000 back payments for consulting services. Not sure what those services are, but very flirty texts.

Past texts included things like, Eric, I wish you would stop papering all these things. What a nightmare. You'll literally cost me my life. I'm going to have to go to the embassy and the embassy will stop writing as they're exchanging about their financial relationship. That seems bad.

Susan Glasser (1:58)

You know, I'm still recovering from the Don Jr. Wedding scandal which I'm, I guess Kimberly Guilfoyle is also still recovering from. But, you know, look, Tim, this is the classic genre of in any other administration, dot, dot, dot. This would be a gigantic, huge, enormous scandal, right? But, I mean, come on, you know, Jared Kushner's father, the convict, is the US ambassador to France. You know, our most prestigious ambassadorship, aside from the position in Great Britain, that's a man who literally hired a prostitute, according to prosecutors, to entrap his own family members in a business dispute. So, you know, I mean, $100,000 AmEx bill, not good, I'll admit. I have to say that I woke up this morning and what I was wondering was, how do you spend $100,000 on an AmEx bill? Is that like, is that all makeup?

Tim Miller (3:02)

I mean, I assume that private jet companies take AmEx, probably that, you know, you don't want to be with the riff-raff.

Susan Glasser (3:11)

The private jets, I mean, isn't she like getting rides from people for that?

Tim Miller (3:15)

I think that we're going to learn that she's getting a lot of things.

Susan Glasser (3:18)

Okay, so I would first of all like an itemized bill. Second of all, in the category of the Jeopardy, you know, category of, you know, Trump family and associates corruption, you know, where is this one going to rank? I will say this, prosecutors and investigative journalists know one thing once they've been doing it for a while, and that is that a story like this doesn't just land out of the blue. There's no way that was the first time she asked somebody for a favor like that. I think ask any editor when they see someone who's been caught for plagiarism, for example.

It's not the first time that it happened, the time that the person got caught.

Tim Miller (3:57)

Yeah, I mean, I've never asked anybody for 100 Gs. So, you know, I don't have any expertise here. But yeah, my understanding and feeling is probably, once you get comfortable, just send in signal chats. Honey, baby, send me six figures.

You're probably doing that.

Susan Glasser (4:12)

She could even call.

Like, I mean, I feel like for $100,000, that's a huge amount of money, at least in the world. Like, maybe worth a phone call.

Tim Miller (4:22)

Yeah, maybe worth a phone call. He told her later that over the years, we should say she did not get this $100,000 from him. He said it would cost him his marriage. Another interesting thing to say. $300,000, though, he said that he had given her in the past for various favors that he wanted. He wanted to go and talk to Carlson Show. He had a tax dispute. He wanted to talk to the IRS head. And so he paid her $300,000 in the past. Close says he didn't get anything for it. But I don't know. We will see. He's kind of an interesting character himself. This whole world is insane. And he was a snappy tomato pizza. Have you ever had a snappy tomato pizza?

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