Susan Glasser: Trump Has a Man Problem

October 8, 2026

AI Summary

5 min read

Trump Has a Man Problem

The Trump administration's self-styled macho men are running ads quoting Biggie Smalls ("If you don't know, now you know") and threatening enemies with "fuck around and find out" — but the war they started in Iran is now seven months in, American bases across the Middle East are destroyed and abandoned, and the president keeps falling asleep during photo ops. As Susan Glasser put it: "The self-styled macho men of this administration seem to have a man problem."

The Corruption Machine Keeps Humming

The episode opens with the latest installment in what Glasser calls the "classic genre" of Trump-world scandal: Kimberly Guilfoyle, Don Jr.'s former partner and current ambassador to Greece, texted a Trump donor asking for $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," she wrote, with a prayer hands emoji. The donor, Eric Dieters, said he'd already given her $300,000 over the years for favors — getting him on Tucker Carlson, connecting him with the IRS head — and gotten nothing in return.

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What you'll learn

1 (01:40) **Welcome and Setup** - Tim Miller introduces Susan Glasser, New Yorker staff writer and co-host of the Political Scene podcast, as she returns for her 20th appearance on the show.
2 (02:11) **Kimberly Guilfoyle's Ambassador Scandal** - The Wall Street Journal story breaks that Kimberly Guilfoyle sought $100,000 from a Trump donor to pay her American Express bill, asking for no paper trail.
3 (06:51) **The Trump Kids' Corruption Network** - The conversation expands to Don Jr. and Eric Trump's financial dealings, including a Kremlin-connected oligarch paying for Don Jr.'s wedding.
4 (09:40) **Marco Rubio's Strange Athens Speech** - Tim plays audio of Rubio in Greece, lecturing Europe about "awakening from its slumber" and referencing ancient Persian crimes, while his own administration is mired in corruption and war.
5 (16:48) **Trump Operatives in the Balkans** - A New York Times story reveals Trump political operatives James Blair and Chris LaCivita spent days in Republika Srpska helping a pro-Russian party ahead of local elections.
6 (19:49) **Taxpayer-Funded Propaganda Ads** - Miller plays a U.S. government-funded ad featuring Marco Rubio quoting Biggie Smalls, bragging about the Venezuela mission, despite Trump claiming his super PAC would cover such costs.
7 (23:26) **The Disastrous Iran War** - The conversation shifts to the spiraling conflict with Iran, with the Times reporting that the U.S. is closing bases across the Middle East and limiting power projection.

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Show Notes

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. But Trump also has another corruption problem, courtesy of Trump Jr.'s ex-fiancée, Amb. Kimberly Guilfoyle, who seems to have a habit of calling in very expensive favors. Plus: Rubio is laying the groundwork for 2028, Hegseth is lobbying to keep his job after the midterms, the Democratic establishment is coming together for El-Sayed, Bibi has been very bad for Israel, and Trump has created a long-term security crisis for the West as a result of his Iran war.

Susan Glasser joins Tim Miller.

show notes: