The late paedophile threatened to expose the Microsoft co-founder’s supposed affair with Mila Antonova if Mr Gates didn't reimburse him for tuition costs that Epstein had initially covered for the woman to attend a software coding school, the Wall Street Journal reported.
Epstein blackmailed Mr Gates in the form of an email in 2017, the report claims, after he failed to convince the world's fourth richest man to join a multibillion-dollar charity fund that he attempted to set up with JPMorgan Chase.
The bombshell report adds weight to longstanding speculation that Epstein may have been extorting his powerful network of friends.
According to the WSJ report, the implication behind the message was that Epstein could reveal the affair if Mr Gates didn’t keep up an association between the two men.
“Mr Gates met with Epstein solely for philanthropic purposes. Having failed repeatedly to draw Mr Gates beyond these matters, Epstein tried unsuccessfully to leverage a past relationship to threaten Mr Gates,” a spokesperson for the Gates Foundation told the Journal.
The Microsoft co-founder reportedly met Ms Antonova around 2010, when she was in her 20s. In a YouTube video posted that year, she spoke about meeting Mr Gates at a bridge tournament and playing against him.
"I didn't beat him but I tried to kick him with my leg," Ms Antonova said in the video.
According to the Journal, Ms Antonova was trying to secure funds in order to establish an online bridge tutorial business. She was introduced to Epstein through Boris Nikolic, a close adviser to Mr Gates.
Ms Antonova and Mr Nikolic met Epstein at his townhouse in November 2013 in New York City, where she reportedly sought $500,000 for her initiative to “promote bridge by creating quality tutorials for beginners and advanced players”.
Epstein did not invest in her project but she went on to stay at one of his apartments in New York a year later. He later paid for Ms Antonova to attend software coding school.
While she was looking to set up her initiative, Epstein was attempting to establish his charitable fund with JPMorgan, which would require the multi-billionaires to make a minimum $100m contribution.
Ms Antonova, in a statement to the Journal, said she didn’t know who Epstein was when they met. “I had no idea that he was a criminal or had any ulterior motive,” she said of Epstein.
“I just thought he was a successful businessman and wanted to help. I am disgusted with Epstein and what he did.”
The bridge player declined to comment about Mr Gates.
In 2006, Epstein was accused of sexually abusing minors as young as 14 and pleaded guilty in 2008 to procuring a minor for prostitution.
A so-called “sweetheart deal” saw him spend just 13 months in jail, and was allowed to return to his office during the day.
Rumors that Epstein had been blackmailing his wealthy friends have been circulating for years.
In 2020, the Netflix documentary Jeffrey Epstein: Filthy Rich claimed that the late paedophile had set up surveillance cameras in his Manhattan townhouse as part of a “blackmail scheme” to extort his powerful associates.
Virginia Giuffre told the documentary makers Epstein had said to her “people owe me favours and I’ll never get caught and I can get away with it”.
In his 2019 book Epstein: Dead Men Tell No Tales, author Dylan Howard alleged that Epstein had been a Mossad spy after being introduced to the Israeli spy firm by Robert Maxwell, the father of his longtime associate Ghislaine Maxwell.
The book claimed that Epstein and Ghislaine had lured prominent politicians and celebrities to his proprieties, and filmed them having sex with underage girls.
The tapes’ existence has never been confirmed by authorities.
Epstein’s network included former presidents Bill Clinton and Donald Trump, lawyer Alan Dershowitz, billionaire Les Weiner and Prince Andrew.
All have strongly denied any wrongdoing or knowledge of criminal behaviour.
Mr Gates reportedly started meeting with Epstein after he was convicted of sex crimes. The duo met on numerous occasions beginning in 2011, at least three times at Epstein's Manhattan townhouse, the New York Times previously reported.
“Mr Gates never had any financial dealings with Epstein. As Bill has said before, it was a mistake to have ever met him,” a spokesperson for Mr Gates told The Independent.
His ex-wife Melinda French Gates said that the clandestine Epstein meetings were a factor in their 2021 divorce.
In a 2022 interview with CBS News, Ms French Gates said she went to meet Epstein because she “wanted to see who this man was”, and that she “regretted it from the second I stepped in the door”.
She described Epstein as “abhorrent” and “evil personified”, and said she had nightmares about the meeting afterwards.
The charitable fund was supposed to be a way for Epstein to rebuild his reputation, according to the WSJ report.
Epstein, in emails sent to JPMorgan executives, tried to come off as a close adviser to Mr Gates.
“In essence, this [fund] will allow Bill to have access to higher quality people, investment, allocation, governance without upsetting either his marriage or the sensitvities [sic] of the current foundation employees,” Epstein wrote in an email in August 2011.
The next day he followed up, writing: “Bill is terribly frustrated. He would! like to boost some of the things that are working without taking away from those that are not [sic]."
In October, Epstein sent another email to JPMorgan executives after the company prepared a presentation, writing, “the presentation, is not tailored to [Bill]. He is the only person, the only one, that counts”.
A JPMorgan spokesperson said: “The firm didn’t need him for introductions. Knowing what we know today, we wish we had never done business with him.”
The Journal quoted a Gates spokesperson as saying that Epstein never worked for Mr Gates and “misrepresented their ties in communications with JPMorgan and others”.
In August 2019, Epstein killed himself in a New York City federal jail cell aged 66 as he awaited trial on sex trafficking charges.
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