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Politics

TGIF: The New School of American Diplomacy

Avery Collins
Last updated: October 16, 2026 10:51 am
Avery Collins
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Welcome back to another week in review with me, returned from a very understated eye lift. I initially said I want the White House Lady Lift but we settled on “refreshed” and “a young 40,” since my doctor said it was the most realistic. (Mom, if you’re reading this, it’s a joke. I still look like hell.)

In Free Press news, October supper clubs are coming up fast. The date is October 22. The location: 46 neighborhoods, 5 countries—this time including Australia! The last day to sign up is Monday, October 19, at 6 p.m. ET. Sign up here for a spot at a Free Press dinner in your town.

Now, onto the news.

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→ Oh, Kimberly: Kimberly Guilfoyle—ex-wife of Gavin Newsom, ex-fiancée of Donald Trump Jr., and as of this week, ex-ambassador to Greece—was offering to trade political favors for cash, according to The Wall Street Journal. I guess she didn’t deliver on the political favors, since now we have tons of her messages with Republican donor Eric Deters. They’re devastating. She sent messages to Deters saying things such as: “You could just send it here. It won’t show up anywhere if you wire money to American Express that’s all that will show. Please.” And: “Honey please I need you to get this done for me today.” And: “Eric, I really wish you would stop papering all these things. It’s really dangerous and not helpful to you or me while you could simply just call me on [S]ignal.” But it soured because according to Eric: “She never came through on anything.” Eric had little schemes of his own: He wanted the extradition of an Ohio doctor who fled to Pakistan after being charged with defrauding insurers. Complex, interesting. (Kim denies it all and claims the messages were AI-generated.) Now Kim is out as ambassador to Greece. Trump has shown little mercy, saying “she wasn’t a member of my family” and “I guess she dated my son a long time ago.” Which is brutal. She and Don Jr. owned a house together, Trumpo! They were engaged! And Trump is like, I think they made out at a bar once, who knows. The Wall Street Journal sums it up: “With two million Instagram followers and her constant travel companion, the stylist Fancy James, she became a potent symbol of the new school of American diplomacy.” The new school of American diplomacy is just asking for money on Signal and having a man named Fancy steam your blazer. We used to be a proper country.

The problem with ol’ Kimmy is that she tried to scam like the big boys, and she couldn’t. But a woman like Kimberly Guilfoyle requires ill-gotten riches. That’s the whole aesthetic. There’s no other career path for Kimberly Guilfoyle. Would a wealthy reader please marry her, accept Fancy James into your life, stick him in a guest bedroom, and just calm this whole situation down? She’ll do some light insurance fraud and you’ll be so happy together. She’ll tape up her eyelids for New Year’s and everything. America’s almost-Fourteenth Lady of West Palm may not deserve power, per se, but she’s at least earned the right to an afternoon of pinot and chopped salad at the club.

→ OpenAI’s bug: An OpenAI engineer allegedly tried to spy on the company by bugging a conference room television. According to authorities, after the bug was discovered, the suspect was then caught on a secret camera checking behind that conference room television to make sure it was still there.

The engineer, Abdulrahman Alfozan, is a well-connected Saudi national. He is reportedly a venture partner at Raed Ventures, a Saudi firm where a member of the royal family is also a partner. He allegedly had a one-way ticket to Saudi Arabia for himself, his wife, and another family member not long after installing the spy device, but alas, the FBI arrested him before he could get to sunny Riyadh. The best part is that he is suspected of plotting his spying using. . . ChatGPT. From The San Francisco Standard:

A chatbot account tied to Alfozan’s spouse, which shared identifiers with his own account, submitted prompts between Sept. 24 and Sept. 30 about building, installing, obscuring, and remotely accessing a recording device, prosecutors said. Queries included how to “build a continuous audio recorder” and “encrypt the SD card,” prosecutors claimed. On Sept. 27 and 28, the account asked about the specific device that was later found, including its unique MAC address.

It’s perfect. The image of his little face peering behind the TV. Using ChatGPT to help. No other nation has good ideas right now, so they just send their sons to California to steal ours. Also, the fact that OpenAI caught the suspect on camera? TGIF salutes OpenAI. Put a camera behind all the televisions. Bug the toilets. Wire the coffeemaker. And know that anytime you enter any space in San Francisco, you are being watched, on the record, and seconds from house arrest.

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