Michael Wolff, the best-selling author, has detailed the “oh-my-God moment” that unfolded the first time he met Jeffrey Epstein.
Wolff said on his Howl Substack that his introduction to the pedophile came on a flight from New York City to the TED conference in Monterey aboard Epstein’s now-infamous private jet in 2000.
The 72-year-old author said Epstein—then still years out from his conviction for soliciting prostitution from a minor—welcomed him and a set of other TED attendees alongside “three model-tall young women.”
“The dodginess could not be missed,” Wolff wrote.

Things got dodgier when Epstein, then 47, began telling one of the passengers, New York architect David Rockwell, about an island he was developing in the Caribbean, asking him to review the blueprints, Wolff recalled.
“He clearly became more confounded as he looked more closely, and as Epstein chattily describing the extent of his other-worldly seeming project. ‘What are these little rooms here?’ a puzzled Rockwell finally asked, pointing to an area that might seem to resemble a medieval cloister,” Wolff wrote.
According to the author, Epstein responded flatly, “That’s where the girls stay.”
Wolff wrote that when Rockwell asked about a “large open area” on the estate, Epstein told him, “That’s where they comb each other’s hair.”
The Daily Beast has reached out to Rockwell for comment.
Wolff noted that the exchange reads as an “oh-my-God moment” in hindsight, though it already struck him as odd at the time. “Okay, this was weird; this was outside the norm—not least of all because whatever it was, a genial Epstein was treating it as perfectly normal,” he wrote.

Little St. James Island has become known as “the hub” of Epstein’s sex trafficking. Epstein bought the island for roughly $8 million in 1998, according to CNN, and shuttled scores of young girls to the island, where they would be sexually abused.
A lawsuit filed by government attorneys in the Virgin Islands alleges that Jeffrey Epstein began his sex trafficking operation on the island 2001, continuing until 2019, when he faced federal sex trafficking charges and later died in jail. According to the lawsuit, victims were as young as 12 years old. Some reportedly attempted to escape the island by swimming.

Wolf wrote that at the end of the TED conference, which Epstein attended, he “hitched another ride” on Epstein’s plane as they were both headed to Los Angeles.
The author recalled that with just Epstein, his three pilots, the three young women on the plane, the pedophile asked him whether he wanted to join him in the “petting zoo.”
“‘Do you want to ride back here in the petting zoo?’ I thought I heard him say, without immediate comprehension, and, very slowly, second-guessing if I could have possibly heard him correctly—and, if I had (long before the interpretation of this might have been obvious), what could this possibly mean. ‘Or up in the cockpit with the pilots?’” Wolff wrote, adding that he opted for the cockpit.
Like the so-called “Pedophile Island,” Epstein’s plane—nicknamed the “Lolita Express”—was a site of the disgraced financier’s crimes. Many of his victims were ferried between his residences in Manhattan, Palm Beach, and the island aboard the plane.
Wolff, who is co-host with Joanna Coles of the Daily Beast’s hit podcast Inside Trump’s Head, has faced scrutiny over his correspondence with Epstein. The veteran journalist has said his goal was to “get the story of the convicted pedophile” and uncover the truth about Epstein’s ties to Donald Trump.
Wolff is publishing a Substack series on his interactions with “the devil in real life,” covering only what he says he “personally saw or heard.”
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