In late January, the U.S. Department of Justice released what it described as its largest batch of files related to Jeffrey Epstein, the financier and convicted sex offender whose network of connections to high-profile figures has fueled ongoing investigations and public scrutiny. The documents, totaling three million pages, 180,000 photos, and 2,000 videos, were made public amid the second Trump administration, shedding light on Epstein's interactions with celebrities, politicians, and business leaders. While much of the release has drawn attention to serious allegations of misconduct, the files also include a range of miscellaneous correspondence and details that reveal Epstein's social orbit in unexpected ways.
Epstein, who died in 2019 while awaiting trial on federal sex trafficking charges, maintained ties with numerous entertainment industry notables, as evidenced by emails and records in the latest disclosure. According to reports from Slate, these files highlight casual interactions that range from dinner invitations to gift exchanges, offering a glimpse into Epstein's efforts to cultivate relationships despite his criminal history. The release comes years after Epstein's 2008 plea deal in Florida and subsequent federal charges, underscoring the persistent interest in his case.
One prominent figure mentioned is filmmaker Woody Allen, who lived near Epstein in New York and exchanged frequent correspondence with him and his wife, Soon-Yi Previn. In 2015, Epstein arranged for Allen and Previn to tour the White House, though he himself was excluded due to perceived risks associated with his reputation. White House counsel Kathy Ruemmler extended the invitation to the couple, according to the files. Epstein also spent lavishly on gifts for Allen, including $9,858 on shirts and boxer shorts from the Swiss luxury brand Zimmerli, as reported by the New York Times. Additionally, Allen and Previn received DNA kits from Epstein, among other friends on his list.
Soon-Yi Previn, adopted daughter of Mia Farrow and wife of Allen since 1997, emerges in the files with pointed remarks about actor Timothée Chalamet. In a 2018 email to Epstein, Previn wrote, “I’m glad that prick Chalamet’s movie did not get a good review,” referring to Chalamet's role in Allen's film A Rainy Day in New York. She added, “No I’m not vindictive,” in the same message. Previn also sought Epstein's assistance in 2018 to help get her and Allen's child into Bard College, a request Epstein fulfilled. These exchanges occurred amid broader #MeToo discussions about Allen's past accusations of abusing his daughter in the early 1990s, which he has denied.
Chalamet, an Academy Award nominee for Best Actor, appears indirectly through Previn's grudge and comments from publicist Peggy Siegal. Siegal, a frequent Epstein associate, emailed that her “friend Timothy Chalemet” [sic] was forced by his team to publicly regret working with Allen, despite not wanting to. Chalamet had expressed remorse in 2018 for starring in the film amid reevaluations of Allen's history. The files portray Chalamet as largely uninvolved, with Siegal's account unverified.
Magazine editor Tina Brown, known for her work at Vanity Fair and The New Yorker, is noted for resisting Epstein's invitations. In 2010, Siegal attempted to lure Brown to a dinner hosted by Epstein for Prince Andrew, also attended by Allen and journalist Charlie Rose. Brown recalled screaming at Siegal, “What the fuck is this, Peggy? The paedophile’s ball?” as she revealed in her newsletter. The files show Epstein and Siegal scheming to “neutralize” Brown's criticism, efforts that failed. Brown, who has seen her reputation bolstered by the disclosure, did not attend the event.
Wellness author Deepak Chopra exchanged emails with Epstein discussing personal matters, including women and celebrity connections. In one thread, Chopra asked Epstein, “Did you find me a cute Israeli?” They also explored linking Leonardo DiCaprio with Woody Allen. A particularly bizarre anecdote involved Marla Maples, former wife of Donald Trump: Epstein claimed he lost a $10,000 bet to Trump when Maples announced her pregnancy, sending Trump a “truck of baby food” afterward. He added that Maples could recount a story about a friend “who was caught having sex with her shoes,” likely referencing a 1990s scandal involving her publicist on trial for stealing 70 pairs of her shoes and engaging in other inappropriate acts, according to the Daily Beast. Chopra has since apologized for his “poor judgment” in associating with Epstein but denied any wrongdoing.
Late-night host Stephen Colbert was mentioned tangentially when an unidentified Epstein friend sent him a clip from The Colbert Report. On this week's The Late Show, Colbert joked, “Well, there’s no such thing as bad publicity!” while displaying a mock Times Square billboard with the friend's endorsement: “It’s really funny. Think Jeffrey will enjoy watching.” The interaction appears innocuous, with no evidence of deeper ties.
Journalist Katie Couric attended a 2010 dinner at Epstein's home, later describing it as “creepy” in her writings. She thanked Epstein afterward, calling the lasagna “ROCKIN” in an email. The following year, Couric ironically emailed Siegal, saying the invitation had landed her in a “world of trouble.” Siegal forwarded this to Epstein, warning of a “witch hunt going on against you and Andrew,” referring to Prince Andrew. Couric has previously discussed the event publicly.
Skateboarder Tony Hawk's name surfaced in an FBI tip included in the files, where a tipster claimed Hawk held a wedding on Epstein's Little St. James island. Hawk clarified on Instagram that none of his four weddings occurred there, though his third was on an island photographed by Mark Epstein, no relation to Jeffrey. The tip remains unverified.
Filmmaker Mira Nair, mother of New York State Assemblymember Zohran Mamdani, attended a 2009 party at Ghislaine Maxwell's townhouse after a film premiere, according to an email. Epstein was reportedly not present. Circulating AI-generated images depicting Nair, Epstein, and Mamdani together have been debunked as fake.
Author J.K. Rowling was referenced when Siegal sought an invitation for Epstein to the 2018 Broadway premiere of Harry Potter and the Cursed Child. Siegal did not disclose Epstein's name in the correspondence, and Epstein was denied entry upon arrival. Rowling has denied any involvement, consistent with the files.
Skincare entrepreneur Peter Thomas Roth sent Epstein a 2018 care package with moisturizer and masks. His brand stated on Instagram that Roth knew Epstein from high school at the Dalton School, where Epstein taught, and they maintained casual contact. No further implications were suggested.
Publicist Peggy Siegal stands out as a key connector in the files, frequently name-dropping elites like Julianne Moore, Henry Louis Gates Jr., and George Lucas in emails to Epstein. In return, Epstein provided her private plane rides and financial advice. Siegal's role bridged Epstein to Hollywood, amplifying his social reach.
Comedian Jon Stewart was floated in discussions about rehabilitating Allen's image, with Epstein and associates considering “someone like Stewart” to narrate a comedy special. Stewart responded humorously, saying, “Excuse me? I am offended. Somebody like Jon Stewart, or Jon Stewart? My point is, do I have the offer, or is this an audition?” Lifestyle figure Martha Stewart shared Epstein's contact details in 2013 and was invited to dinners with Allen and Previn. NFL quarterback Russell Wilson was approached in 2019 by Epstein's pilot about buying his Gulfstream G-IV jet. Wilson denied any knowledge on X, stating, “Not TODAY satan! … Some Random plane broker tried to sell me a plane. I had no idea whose plane and never bought the plane.”
The release of these files continues to ripple through public discourse, prompting statements from those named and renewed calls for transparency in Epstein's network. While many connections appear peripheral, they highlight the breadth of Epstein's influence before his death. Officials have not indicated further releases, but legal experts anticipate ongoing analysis could yield more insights into his operations.