Looking for another reason to steer clear of convicted sex offenders? They can and will blackmail you, a lesson Microsoft co-founder Bill Gates may have learned the hard way according to a new report from the Wall Street Journal.

Disgraced financier and convicted sex offender Jeffrey Epstein allegedly attempted to blackmail Gates after learning he had reportedly had an affair with Russian bridge player, Mila Antonova.

Though Gates and Antonova first met around 2010, when they were respectively in their 20s and 50s, Epstein met the bridge star in 2013, before later paying for her to attend coding school.

In 2017, roughly four years after he first met Gates, Epstein reportedly sent a pointed email requesting Gates reimburse him for Antonova’s tuition, an ask that was likely more than just an IOU between the billionaires, who had “met” on “numerous occasions” since 2011, per the New York Times.

“The implication behind the message, according to people who have viewed it, was that Epstein could reveal the affair if Gates didn’t keep up an association between the two men,” explained Khadeeja Safdar and Emily Glazer, who penned the article.

Epstein, who died in prison while awaiting trial for sex trafficking charges in August 2019, sent the message after Gates declined to work with the financier on a “multibillion-dollar charitable fund with JP Morgan” designed to “pool money from some of the world’s wealthiest people,” per the Wall Street Journal.

Looking to benefit from both the fund’s fees and the optics of such an endeavor  – Epstein who was convicted of soliciting prostitution from a minor and soliciting prostitution back in 2008 – needed Gates’ backing on the project.

Unlike his associate, Gates’ once strange reputation had undergone quite a transformation. By the late 20-teens, Gates, to the non-conspiracy-peddling majority, had been crowned as one of the pop finance world’s most wholesome figures. He regularly dominated headlines for his philanthropic achievements (Bill Gates walked so MrBeast could run), his status as “billionaire besties” with Berkshire Hathaway CEO Warren Buffett and his tidbits of professional advice, tips that appeared wholesome against the incoming wave of social media “hustle porn.”

Even Gates’ past mistakes were frequently reported through the rose-colored lenses of his later achievements. His penchant for dropping f-bombs in meetings, memorizing employees’ license plates to track their whereabouts, and sending pointed “flame mail” all hours of the night were rebranded as comical anecdotes in one man’s success story, sometimes even heralded as a shining example of motivating workers.

Shortly after Gates and his wife announced their separation in May 2021 – a decision that allegedly stemmed from her concerns surrounding her partner’s connections with Epstein –  several of his purported indiscretions and “reputation for questionable behavior,” as the New York Times called it, seeped from the confines of his inner circle and into the press. Stories detailing Gates’purported habit of pursuing women who worked under him at both Microsoft and the Bill and Melinda Gates Foundation, the sexual harassment claims against him, and of course, his friendship with Epstein began swirling.

Giving convicted sex offenders your email: not even once.