‘Playing with fire’: Jeffrey Epstein bankrolled a woman tied to Bill Gates—then asked to be repaid

“Playing with fire.” Recommended Video So read an April 30, 2018 email Jeffrey Epstein sent to Bill Gates’ chief of staff, Larry Cohen, according to files released by the Department of Justice. Epstein had just put up Mila Antonova in one of his Upper East Side apartments for the week, he told Cohen. Antonova, a Russian bridge player who told Fortune through her lawyer that she had “a relationship” with Gates around 2010, and has been reported elsewhere to have been his mistress, had been receiving financial help from Epstein for years. Epstein wanted Gates to know. In fact, Epstein had wanted Gates to know for a long time. Documents released in January by the DOJ show that between 2013 and at least 2018, Epstein helped organize Antonova’s visa, wired her cash, housed her repeatedly in various apartments he kept in Manhattan, and paid for her coding education. Later, Epstein referred to those payments and pressured the billionaire founder of Microsoft to reimburse him, the emails show. In one exchange, Epstein invoked the “sanctity of friendship.” In a July 29, 2017 email to Cohen, he quoted what he claimed were Gates’ own words: “If you can help push this out three years that should be enough” — a reference, Epstein said, to housing and bankrolling Antonova after her relationship with Gates ended. Three years had now passed, Epstein wrote. He had “paid for school, helped organize visa,” and Antonova had “to stop bridge tournaments, living day to day on a friends couch with no air con.” “I know you and Bill share my views on the sanctity of friendship,” he wrote to Cohen. The pressure campaign around the payments to Antonova was part of an extensive and complex effort by Epstein to bore his way into Gates’ inner circle and to benefit from the Microsoft cofounder’s contacts and influence. Fortune reported on that effort earlier this week. Antonova’s attorney told Fortune she had neither knowledge of Epstein’s efforts to pressure Gates, nor provided “services, information or any other assurance or act in exchange” for his support. The lawyer said Antonova “naively accepted” Epstein’s help, believing he genuinely wanted to assist her. Five months before he was arrested for conspiring to sex-traffic minors in 2019, Epstein was still emailing Gates asking to be repaid. “As Gates has said consistently, he regrets meeting with Epstein,” a spokesperson for Gates wrote to Fortune . “The files show just how extensively Epstein worked to insert himself into Gates’ life—both directly and through others in Gates’ orbit—and how Epstein continued in these efforts even after Gates stopped meeting and communicating with him. To be clear, Gates never witnessed or engaged in any illicit or illegal behavior.” Cohen, who was then not only Gates’ chief of staff but also a managing partner at Gates’ private office, Gates Ventures, did not respond to Fortune’s request for comment. (Cohen is now at venture firm Biomatics Capital.) Antonova’s attorney confirmed in a letter to Fortune that Antonova met Gates at a bridge tournament in 2009 and “maintained a relationship with him for a time.” ‘Mila happened’ Epstein’s relationship with Antonova began with Boris Nikolic, then-Gates’ chief science adviser at the Gates Foundation and at his investment firm, Bgc3. Nikolic was also one of Epstein’s most frequent correspondents, with the two exchanging thousands of emails in the decade between 2009 up until Epstein’s death in 2019. On May 23, 2013, Nikolic—then still at the Gates Foundation—emailed someone who appeared to be an immigration attorney about Antonova, describing her as a Russian friend who had “overextended her stay in USA” on a boat crew visa. The case, he wrote, would “need to be VERY creative,” adding he was “willing to cover the cost.” Antonova’s attorney confirmed to Fortune that Nikolic referred her to an immigration attorney but disputed that he offered to cover the fees, instead saying Antonova and her “then-husband” paid. Antonova’s last contact with Gates, according to her lawyers, was in May 2013—around the time Nikolic reached out. That summer, according to the documents, Nikolic’s own working relationship with Gates began to collapse. By September, he exited the foundation with a $5 million advance. In a late-night email to Epstein that November, Nikolic tried to piece together a timeline from his inbox of what had happened between himself and Gates. On May 22, the day before he emailed the immigration attorney, he wrote, “Mila happened.” Three weeks later came a Paris meeting between Epstein and Gates that both men mention in the DOJ emails. A month after that, Nikolic said, Gates sent him an email about “Melinda finding out” and that their working relationship had to end. Epstein’s reply came just after midnight: “He cries because he knows it is wrong. Not because he is sad.” “Epstein was a master manipulator, and I deeply regret associating with him,” Nikolic wrote in a statement to Fortune . He has not been char