When the late sex offender and financier Jeffrey Epstein heard word of an affair Bill Gates had with a 20-something Russian bridge player, he held it over the Microsoft co-founder’s head, sources familiar with the matter told The Wall Street Journal. Although Gates and Epstein previously met to discuss philanthropy, Epstein had an interest in roping Gates into a proposed multibillion-dollar charitable fund with JP Morgan Chase—which ultimately failed. The resentment appeared to boil back up in a 2017 email exchange between the rich men over Gates’ mistress, Mila Antonova. Epstein met Antonova in 2013, three years after Gates’ own encounter, and later financed her enrollment in software coding school, The Wall Street Journal reported. Gates then received an email in 2017 from Epstein requesting he be reimbursed for Antonova’s course, which sources said was a subtle threat from the financier to leak the affair if he didn’t agree to keep up a relationship with Epstein. “Having failed repeatedly to draw Mr. Gates beyond [philanthropic] matters, Epstein tried unsuccessfully to leverage a past relationship to threaten Mr. Gates,” a spokesperson for Gates told The Journal. Antonova declined to comment on Gates.