‘Playing with fire’: Epstein bankrolled Bill Gates’ reported ex-girlfriend for years—then asked Gates to ‘reimburse’ him five months before he died

“Playing with fire.”

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 charged with any wrongdoing.

Gates later confirmed the affair. In a town hall last month with Gates Foundation staff, according to the Wall Street Journal, he told employees he “had affairs”—including one “with a Russian bridge player who met me at bridge events.” He said Nikolic knew of the affairs and told Epstein about them.

How it started

On July 14, 2013—in the middle of negotiating Nikolic’s own exit from the Gates Foundation—Epstein brought up Antonova with Nikolic for the first time in their correspondence: “Ask the attorney that was helping Mila, for her status?” By November, Epstein had meetings scheduled with both Nikolic and Antonova, DOJ documents show.

Over the next year, Epstein funded at least part of Antonova’s life. On Oct. 9, 2014, he emailed his accountant Richard Kahn with wire instructions for an entity called Bridge Union Inc.: “Rich send 7k this month to Mila and again next month.” Emails between Epstein’s assistant Leslie Groff, Antonova, and building staff also show Groff sending apartment details and door codes to apartments Epstein maintained in the Upper East Side.

“Everything is great,” Antonova emailed Groff in late November 2014. “Thank you for accommodating me.”

Antonova’s attorney confirmed Epstein made “several unsolicited monetary gifts,” paid for her coding education, and provided use of his apartment “several times” between 2014 and 2018. The lawyer added that Antonova met Epstein in person only twice, that he was never present during her stays, and that she had no reason to believe Epstein was using her situation as leverage.

By mid-2016, Gates had stopped engaging with Epstein directly; his last email to Epstein in the DOJ documents is from December 2014. After that, all communications were filtered through Cohen, whom Epstein didn’t trust and described as “Melinda’s boy” in emails to Nikolic.

Epstein’s response was to make sure Gates knew the connection to Antonova was still alive. On June 15, 2016, he emailed Nikolic what appeared to be a message meant for Gates: “You can tell your boy that I still hear from Mila. I put her through computer school.”

A year later, on July 21, 2017, Antonova wrote to Epstein expressing gratitude: “You and Boris [Nikolic] have done an exceptional thing for me. Created an opportunity for me to grow and have control over my life.” Their help was pivotal in leading to where she was then: sleeping in a friend’s living room in Palo Alto, paying $700 a month for a couch, preparing for tech industry interviews thanks to her coding classes, all funded by Epstein. 

The next day, Epstein emailed Cohen, saying he had heard from “an old friend” of Gates and that they should speak. He told Cohen he planned to keep spending money on “his old friend” but added he had “received neither thanks nor reimbursement.” He gave Cohen a deadline: “If you think I shouldn’t, let me know by tomorrow night.”

‘Your friend Bill is nuts’

Privately, Epstein was dumbfounded about getting the cold shoulder from Gates. On July 25, 2017, he wrote to Nikolic: “Your friend Bill is nuts. His former girl. Can’t afford air con, can’t afford to travel to bridge… that story would take Trump off the front pages. The richest man in the world is so cheap, his former bridge girl and toy, lives on a friend’s sofa. WOWO.”

Cohen sent Epstein an email that said Gates would soon give the “nod” for them to talk. But by Aug. 6, Epstein emailed again: “No acknowledgment from Bill??” Cohen’s response: “He’s been off the grid for a while.”

The silence stretched into December 2017, and Epstein shifted tactics. “The phrase is, I’m about to run out of money,” he emailed Cohen. Cohen reached out asking to talk, but Epstein was done with pleasantries. He replied that he had also emailed Gates directly—“asking why I had no BG approval, nor offer to pay back what was advanced at his request. All odd.”

In April 2018, Antonova stayed in Epstein’s apartment again. Building staff emailed Epstein’s assistants to confirm a welcome letter had been left for “Mila Antanova arriving Thurs. April 26th.” Days later, on April 30, Epstein emailed Cohen with the message that opened this story: “FYI, I had to put up Mila in New York for the week. I was not there. Playing with fire,” he said.

Antonova’s attorney said she had “no knowledge of and cannot speculate about” Epstein’s communications with Cohen and no basis to believe Epstein was using her financial situation as leverage against Gates.

The final ask

On Jan. 5, 2019, Epstein emailed Gates directly: “I think at some point you want to reimburse me… I feel awkward asking.”

Four days later, he wrote to Gates and Cohen again, requesting a meeting: “I think best that when Bill is on the East Coast, we set aside an hour to meet.”

It’s unclear if Epstein ever received a response. Shortly after, he began assembling a paper trail, asking an associate to dig through “past photos and emails” to establish when Epstein and Nikolic had first met Gates at an airport in Washington, D.C.—an apparent reference to a meeting at Reagan National that Nikolic had helped arrange in December 2013.

On Jan. 20, 2019, Epstein emailed Gates: “I hope you follow Bezos’ lead.” It’s not clear from the emails what Epstein meant. Ten days earlier, Jeff Bezos had announced his divorce from MacKenzie Scott shortly after the National Enquirer reported on Bezos’ extramarital affair with Lauren Sanchez.

Five months later, Epstein was arrested for conspiring to sex traffic minors. A month after that, he was found dead in his cell at the Metropolitan Correctional Center in Manhattan. 

Gates, who has not been charged with wrongdoing, was called on last week to testify before the House Committee on his ties with Epstein.

This story was originally featured on Fortune.com