Epstein Alleged billionaire Bill Gates left ex-mistress penniless and sleeping on a couch

Supposedly, the billionaire’s famous philanthropy did not extend to his extramarital affairs.

Bill Gates is facing intense scrutiny for his relationship with Jeffrey Epstein following a tranche of files released by the Justice Department on January 30. In a 2017 email, Epstein claimed that Gates had left his Russian ex-mistress “broken” and sleeping on a friend’s couch — and that if her perilous financial situation had been made public, Donald Trump would have been in the headlines.

Gates, 70 – who is worth an estimated $104 billion, making him one of the 20 richest people in the world – has been one of the most prominent victims of the ongoing release of the Epstein files.

The Epstein files suggest that the financier (R) and Gates were closely related.

In an email sent from Epstein’s personal Gmail account to Gates adviser Boris Nikolic about the Microsoft founder, Epstein wrote in July 2017 that Gates’ “former bridge girl” — who appears to be Mila Antonova, a bridge player nearly 30 years younger than Gates — was “free” and “had little money.”

Epstein claimed he was “sitting on a friend’s couch” and “really needed money”, before adding: “I sent him some money.”

In the misspelled email, the convicted sex offender then mocked Nikolic’s “buddy bill” as “crazy,” saying “Gates’ ex-girlfriend…can’t afford air conditioning, can’t afford (sic) to travel to bridge.”

Epstein said: “The richest man in the world is so cheap, his ex-bridge girl and toy, he lives on a sofa with friends”, adding: “That story would take the front pages.”

At the time Epstein’s email was sent, Trump was engulfed in fury over the Trump Tower Russia meeting after Donald Trump Jr. released emails showing he welcomed “very high-level and sensitive information” from a Kremlin-linked lawyer about Hillary Clinton.

Gates (R) has remained close to Donald Trump since Trump became president and was part of a group of tech leaders who attended a dinner in the State Dining Room of the White House in September 2025. / SAUL LOEB / SAUL LOEB / AFP via Getty Images

Gates (R) has remained close to Donald Trump since Trump became president and was part of a group of tech leaders who attended a dinner in the State Dining Room of the White House in September 2025. / SAUL LOEB / SAUL LOEB / AFP via Getty Images

The episode dominated cable news and front pages as Robert Mueller examined whether the meeting violated campaign finance laws or conspiracy laws, though prosecutors did not bring any charges for the meeting.

Epstein’s email appears to refer to Antonova, who, according to a May 2023 report in the Wall Street Journal, had an affair with Gates around 2010, when she was in her twenties. According to the Journal, Epstein later met Antonova in 2013 after Nikolic introduced them and agreed to pay for her software coding course.

Gates and his alleged former Russian mistress, Mila Antonova. / IginiteNYC/YouTube

Gates and his alleged former Russian mistress, Mila Antonova. / IginiteNYC/YouTube

Four years later, in 2017, Epstein emailed Gates demanding repayment, in a move widely interpreted as an attempt to gain power over one of the world’s richest people, according to the Journal. The Daily Telegraph later reported in 2023 that Antonova was associated with “notorious” Kremlin spy Anna Chapman.

Chapman, a glamorous member of a Russian spy ring, was exposed as a sleeper agent and deported from the US in 2010. / Contributor / Getty Images

Chapman, a glamorous member of a Russian spy ring, was exposed as a sleeper agent and deported from the US in 2010. / Contributor / Getty Images

Gates said his meetings with Epstein were only about philanthropy and that they were “a big mistake.” A spokesman insisted that Epstein’s attempts to present himself as a Gates adviser were lies and that “Mr. Gates had no financial dealings with Epstein,” including regarding Antonova’s tuition.

“Mr. Gates met with Epstein solely for philanthropic purposes. Having repeatedly failed to woo Mr. Gates beyond these matters, Epstein unsuccessfully attempted to leverage a prior relationship to threaten Mr. Gates,” a Gates spokesperson told the Daily Beast.

Antonova previously told the Journal that she didn’t know who Epstein was when they met and thought he was simply a wealthy businessman offering to help her teaching startup. She said he later let her stay briefly in an apartment in New York, but they barely interacted and she is now “disgusted” by what she has learned about him.

Nikolic, a physician-investor who was Gates’ chief scientific adviser from 2009 to 2014, said he first met Epstein in his official capacity for Gates, now regrets the contact and denies having any business ties to the pedophile financier.

Bill Gates and Boris Nikolic pictured together in 2012. / Paul Morigi / Getty Images

Bill Gates and Boris Nikolic pictured together in 2012. / Paul Morigi / Getty Images

The Antonova memo is part of a wave of material released under the Epstein Files Transparency Act, which has forced the Justice Department to release millions of pages of Epstein-related documents, including emails, photos and videos.

Lawmakers on the House Oversight Committee also posted their own cache of Epstein communications while blaming the DOJ for withholding large portions of the files.

It’s the latest damning allegation to hit Gates in the files. On Monday, the Daily Beast reported on draft emails from 2013 in which Epstein appeared to write a message to Nikolic, accusing Gates of contracting a sexually transmitted infection after “sex with Russian girls” and plotting to get his then-wife, Melinda French Gates, antibiotics without her knowledge.

Gates’ spokesman called the claims “absolutely absurd and completely false.” French Gates later said that dropping the document brought back “very, very painful” memories of their marriage.

Bill Gates and Melinda French Gates divorced in 2021 after 24 years of marriage. French Gates said Gates' relationship with Epstein contributed to the breakup of their union. / Lou Rocco / Lou Rocco/Disney General Entertainment Content via Getty Images

Bill Gates and Melinda French Gates divorced in 2021 after 24 years of marriage. French Gates said Gates’ relationship with Epstein contributed to the breakup of their union. / Lou Rocco / Lou Rocco/Disney General Entertainment Content via Getty Images

Gates has emphasized in several interviews that he never visited Epstein’s island, never met women through him, and that the relationship consisted of a handful of dinners from 2011 onwards, which he now regrets.

In an interview with Australia’s 9 News that aired Wednesday, Gates was pressed directly about his ties to the convicted sex offender. He said: “The focus was always, he met a lot of very rich people and said he could get them to give money to global health.

Trump is also under pressure over his ties to Epstein. The president has repeatedly denied knowing about any of the financier's criminal activities. / Davidoff Studios/Getty Images

Trump is also under pressure over his ties to Epstein. The president has repeatedly denied knowing about any of the financier’s criminal activities. / Davidoff Studios/Getty Images

“You know, in retrospect, it was a dead end, and I’ve said it many times, but I’ll say it again: I was stupid to spend time with him. I was one of the many people who regret ever knowing him.”

Epstein, who died in a New York prison in 2019 at the age of 66 while awaiting trial on sex-trafficking charges, spent the last few years trying to monetize his connections to billionaires and world leaders — and, as this latest email shows, often bashing them in private.

The Daily Beast attempted to reach Antonova for comment.

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