This reporting is featured in this week’s edition of Confider, the newsletter pulling back the curtain on the media. Subscribe here and send your questions, tips, and complaints here.
Gossipy provocateur and author Michael Wolff has long been accused of being too chummy with his highest-profile subjects, which at one point included Jeffrey Epstein. New documents obtained and reviewed by Confider reveal the extent to which the pair spent time together—even after Epstein was found guilty of sexually abusing a 14-year-old girl.
According to newly unearthed scheduling records and emails from the U.S. Virgin Islands attorney general, Wolff and Epstein (who were close in the late ’90s and early ’00s, at one point partnering up to try to buy New York magazine) had at least nine planned meetings between 2012 and 2015.
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These previously unreported meet-ups—which were not disclosed in Wolff’s most recent book Too Famous and its chapter title “The Last Days of Jeffrey Epstein”—provide a unique window into just how much the two socialized even after Epstein served jail time in 2008 and became a registered sex offender.
The first scheduled hang was dated Feb. 16, 2012, a breakfast in New York that listed both Wolff’s cell and email. Confider could not verify whether the meeting took place but confirmed the listed cell number and email do belong to Wolff.
On July 30, 2013, Wolff was listed as having a scheduled lunch with Epstein at 12:30 p.m. in NYC. In early 2014, Wolff was slated for a January breakfast in the city with Epstein as well as a dinner—where Woody Allen, his wife Soon-Yi Previn, and former J.P. Morgan exec Jes Staley, among several others, were listed as attending—followed by two meetings in September and another lunch in October that year. By 2015 they had plans to meet in January for breakfast and on April 8 for a late-afternoon appointment.
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While such engagements could ostensibly be characterized as “source meetings” for a reporter like Wolff, they are certainly curious considering the long-running questions about their connections. New York magazine notably killed Wolff’s rehabby profile of Epstein in 2019 over “fact-checking concerns,” which were later alleged to include the author allowing Epstein to “dictate” the piece and field all fact-related questions, according to Alex Yablon, the fact-checker on the piece.
Wolff did not respond to Confider’s multiple requests for comment about the purpose of their scheduled meetings or what was discussed.
And while Wolff’s book includes that 40-page chapter about Epstein—largely centered on the convicted sex offender’s relationship with Steve Bannon—he curiously made no mention of his own extensive association with Epstein.
However, Wolff has never been shy about sharing his thoughts on Epstein. “He has never been secretive about the girls.” Wolff told New York in 2007. “At one point, when his troubles began, he was talking to me and said, ‘What can I say, I like young girls.’ I said, ‘Maybe you should say, ‘I like young women.’”
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