When Michael Wolff, who’s known for stirring up a storm with his words, claims something new about Donald Trump, almost everyone in politics and beyond sits up and takes notice. They can’t help but listen, even if it sounds a bit out there. And his latest shocker is that Trump and Jeffrey Epstein had an intense, almost crazy, “abiding obsession” for going after supermodels back in the day, when they were tight buddies in the 90s and the early 2000s.
On Erin Burnett’s show, OutFront on CNN, Wolff spoke about his extensive interviews with Epstein. He bluntly stated, “I think it was probably the most important part of their lives. Women and money, money and models.” He went on to explain that both guys had started their modeling agencies and were regulars at fancy fashion parties.
They used to be “chasing models, figuring out how to be with models, figuring out how to get models to like them.”
Donald Trump was also the owner of the Miss USA beauty contest from 1996 until 2015.
Meanwhile, Jeffrey Epstein had a very close relationship with Les Wexner, the ex-billionaire who used to run Victoria’s Secret. It’s said that he took advantage of this connection to get to know a bunch of women. Wolff describes these two guys as being thick as thieves back when supermodels were basically America’s top celebrities.
Back in 1997, there were pictures of Trump and Epstein together, having a good time at a particular Victoria’s Secret party with a Belgian model named Ingrid Seynhaeve. Now, at that time, Trump was married to Marla Maples. But if you look at his past, it’s like he had a type, because he’s also known for dating other models like Kylie Bax and Rowanne Brewer Lane.
This all fits pretty well with the kind of stuff Wolff talks about in his book.
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It doesn’t take a genius to comprehend why a well known author as Michael Wolff could get away with saying this without being sued by Trump:
“Jeffrey Epstein showed photos of Donald Trump with topless young woman sitting on his lap. And there’s one I especially remember where… pic.twitter.com/liZwM1llWF
— Marlene Robertson🇨🇦 (@marlene4719) July 15, 2025
Michael Wolff’s statements might seem like the usual gossip you’d find in a tabloid, but they’re actually coming out at a time when people are looking into things more closely. The New York Times says that Attorney General Pam Bondi told Donald Trump a few months ago that his name pops up in some new documents about Epstein’s case.
The White House is quick to say that just because his name is there, it doesn’t mean he’s done anything wrong.
Well, the situation doesn’t look too good for him. Donald Trump’s past comments praising Epstein as a “terrific guy” who shares his taste for “beautiful women (…) and many of them are on the younger side” are definitely raising eyebrows now.
Too bad it’s figuratively and not literally…
Trump explodes at CNN as Jeffrey Epstein seen beside 12-year-old Ivanka and at president’s wedding in never-before-seen photos.#TrumpPedoFiles https://t.co/dg5dciotbL
— Sergeant Alvin York 🌻 (@acyork1887) July 23, 2025
And let’s not forget his odd defense of Ghislaine Maxwell, saying, “I wish her well.” It’s confusing, really.
NEXT UP: Is Trump’s DOJ Ready to Strike a Deal With Ghislaine Maxwell?
Even though he promised to make the Epstein files public during his 2024 run, his DOJ just announced that the investigation is over and done with. But the political drama surrounding this isn’t going anywhere. Wolff, who talked to CNN, said that “The White House is (…) looking to do anything to close down this story.”
