For more than two decades, Jeffrey Epstein methodically worked his way into Microsoft’s highest ranks, embedding himself in the company’s inner circle through charm, money, and strategic social relationships, The New York Times reports.

One critical unanswered question from the Justice Department’s unredacted Epstein files is whether that access enriched J. Epstein & Co.

Epstein’s first known Microsoft connection dates to a 1996 gala dinner at the Seattle Zoo hosted by Nathan Myhrvold, then a senior technologist who would become Microsoft’s chief technology officer.

Epstein attended as the guest of telecom executive Lynn Forester, according to Linda Stone, a Microsoft executive who sat next to him.

From there, Epstein methodically built relationships.

He stayed in touch with Stone, later a Microsoft vice president reporting to CEO Steve Ballmer.

In 2002, Epstein funded an artificial intelligence symposium Stone helped organize in St. Thomas in the U.S. Virgin Islands — part of his broader strategy of courting elite scientists with promises of financial backing.

He later hosted scientific gatherings in the Caribbean and pitched himself as a benefactor to researchers.

Stone told The New York Times that Epstein was “charming and persistent” in seeking introductions to scientists.

Myhrvold became a key bridge. The former CTO developed a two-decade relationship with Epstein and even contributed to Epstein’s 50th birthday book in 2003.

“A few years ago somebody at a party asked me, ‘Does Jeffrey Epstein manage your money?’” Myhrvold wrote. “I replied, ‘No, but he advises me on lifestyle.’”

Myhrvold included safari photos in the book, including images of animals mating, saying they “seemed more appropriate than anything I could put in words.”

Crucially, Myhrvold vouched for Epstein to Bill Gates.

By 2010, Gates agreed to meet Epstein, writing to aides that “Nathan had agreed with you that I would enjoy meeting with him and that it is a fine thing to do.”

Gates would later call the relationship “a huge mistake.”

Epstein was equally deliberate in exploiting romantic relationships to deepen his access and influence.

In the early 2000s, he supported Melanie Walker, whom he had recruited as a model and later helped through medical school.

Close Tabs on Gates

Walker began dating Steven Sinofsky, then head of Microsoft’s Windows division, and joined the Gates Foundation in 2006. Through Walker and foundation adviser Boris Nikolic, Epstein kept close tabs on Gates.

Nikolic later said he regretted the association, stating Epstein “used lies to pursue his own agenda.”

By 2011, Epstein was receiving inside updates about Microsoft’s CEO succession battle as Steve Ballmer faced pressure amid struggles in mobile and search.

Emails show Epstein got play-by-play information and offered advice during the search process — giving him access to sensitive corporate deliberations.

He portrayed himself as close enough to Microsoft’s leadership that in 2013 he emailed billionaire Tom Pritzker asking, “Any interest in running microsoft?”

Epstein’s influence extended to Sinofsky during Microsoft’s troubled Windows 8 era. As Sinofsky prepared to exit the company, he sought Epstein’s advice on his separation package, sharing details of his proposed payout. Epstein disparaged Microsoft’s lawyers as “idiots” and “goofy.”

More troubling, Sinofsky forwarded Epstein internal executive emails discussing poor Surface tablet sales — confidential company information.

‘Got Paid. You Will Be Too.’

After receiving a reported $14 million payout in 2013, Sinofsky wrote to Epstein: “Got paid. You will be too :)”

Epstein also cultivated Reid Hoffman, LinkedIn’s co-founder and later a Microsoft board member after Microsoft acquired LinkedIn for $26.2 billion in 2016.

Their connection grew through tech and philanthropy circles, including introductions via Joi Ito of MIT’s Media Lab.

Epstein sent personalized gifts — including custom sweatshirts — to Hoffman, Gates and others. Flight logs show Hoffman visited Epstein’s private island in 2014.

Epstein kept close tabs on Gates through Hoffman and others. In one email, Epstein told Hoffman before a New York gathering, “Spoke to bill, he’s glad you are coming.”

In 2015, after a high-profile Palo Alto dinner party attended by Elon Musk, Mark Zuckerberg and Peter Thiel, Epstein thanked Hoffman for the invitation and his “friendship.”

Hoffman later introduced Epstein to Zuckerberg over email “so that the conversation can continue,” though there is no indication Zuckerberg responded.

Fixer & Financier

Epstein positioned himself as a fixer and financial strategist. After Microsoft’s LinkedIn acquisition, he offered Hoffman advice on minimizing taxes. He also advised Hoffman on buying a private jet, telling him he would “hold your hand all along the way.”

When Virginia Roberts Giuffre publicly accused Epstein of sex trafficking in 2014, reviving scrutiny of his crimes, Hoffman told Epstein he had been thinking about ways to help address negative media attention, though specifics remain unclear.

It is not publicly known whether Hoffman assisted Epstein in legal matters tied to Giuffre.

Epstein’s Microsoft connections proved particularly valuable after his 2008 conviction for soliciting prostitution from a minor.

Despite his criminal record, he regained entry into elite tech and philanthropic circles, aided by endorsements and introductions from powerful figures within Microsoft’s orbit.

Across more than two decades, Epstein assembled a who’s who of tech power players in his orbit — Bill Gates, Nathan Myhrvold, Steven Sinofsky, Linda Stone, Reid Hoffman, Boris Nikolic, Melanie Walker and others linked to Microsoft and the Gates Foundation.

Whether Epstein ever invested in Microsoft stock or profited from insider knowledge remains an unanswered question. There is no public evidence showing he traded on confidential information, but the depth of his access raises obvious concerns.