Microsoft was in turmoil in 2011. The company had whiffed on smartphones and internet search. Steve Ballmer, the chief executive, was under pressure, and there was talk of replacing him.
In the middle of the maneuvering was Jeffrey Epstein.
Mr. Epstein received updates on the hunt for Microsoft’s new chief executive from company insiders and offered them play-by-play advice, according to the latest release of documents from the Justice Department detailing the financier’s life before he was jailed in 2019 on federal sex-trafficking charges.
“The plot thickens,” a confidant wrote to Mr. Epstein in a gossipy 2011 note. Microsoft’s search had been delayed, the redacted email said, and the co-founder Bill Gates, who had left day-to-day management, was thinking of returning for nine months.
More than he did at any other major tech company, Mr. Epstein found success boring into the inner sanctums of Microsoft. Leveraging one connection into the next, he became privy to the company’s dramas, from its chief executive succession to the philanthropy of top executives. After Mr. Epstein left prison in 2009 for soliciting prostitution from a minor, his connections to Microsoft executives aided his attempt to return to society.
Mr. Epstein’s moves to develop relationships in other large companies via their founders, including L Brands and Apollo Global Management, were less successful. The files from the Justice Department show that he spent more than a decade developing a network of Microsoft executives, including Mr. Gates; Nathan Myhrvold, a former technology chief; Steven Sinofsky, who ran Microsoft’s Windows division; Linda Stone, a former technology research executive; Reid Hoffman, a Microsoft board member; and employees of Mr. Gates’s personal investment and charity funds.
While some of these people are gone from Microsoft, Mr. Hoffman remains on the board. Mr. Gates, whose relationship with Mr. Epstein has been well documented, advises the company. Mr. Myhrvold attended Microsoft’s 50th anniversary celebration last year.
Mr. Epstein portrayed himself as so close to Microsoft executives that in 2013, he casually solicited the interest of other contacts about leading the company. In an email to the billionaire Tom Pritzker, Mr. Epstein wrote, “Any interest in running microsoft?”
Frank Shaw, Microsoft’s communications chief, said the company was disappointed to read emails between Mr. Epstein and “former Microsoft employees acting in their personal capacities.” Without mentioning a name, Mr. Shaw acknowledged the emails showed that a former executive — who was Mr. Sinofsky — had shared confidential company business with Mr. Epstein.
A spokeswoman for Mr. Gates referred a request for comment to Microsoft. Mr. Gates recently said he had sought to raise money for philanthropy from Mr. Epstein and had nothing to do with Mr. Epstein’s inappropriate behavior with women. He has called his relationship with Mr. Epstein “a huge mistake.”
Mr. Hoffman said in a statement that he wanted the Trump administration to release all files related to Mr. Epstein and prosecute those responsible for criminal behavior. “I welcome all the work that is being done by the press and those online to look into any and all Epstein connections to expose those who committed crimes,” he said.
Mr. Epstein’s first known connection to Microsoft dates to 1996 when Mr. Myhrvold, a technologist who would be named the company’s chief technology officer, threw a gala dinner for the renowned physicist Stephen Hawking at the Seattle zoo. Lynn Forester, a telecommunications executive, brought Mr. Epstein as a guest, according to Ms. Stone, who was seated next to him.
Ms. Forester said in an email that she recalled the gala but not whether Mr. Epstein had been there, adding that she did not speak with Mr. Epstein after 2000.
Mr. Epstein kept in touch with Ms. Stone, who later reported directly to Mr. Ballmer as a Microsoft vice president. In 2002, after she left Microsoft, Mr. Epstein funded a symposium that Ms. Stone helped organize on St. Thomas in the U.S. Virgin Islands on the future of artificial intelligence, along with famous academics.
Ms. Stone said in an interview with The New York Times that Mr. Epstein had been charming and persistent in asking for introductions to scientists he might fund.
Mr. Myhrvold, meanwhile, developed a relationship with Mr. Epstein that spanned two decades and led to more Microsoft connections for the financier. The two were friendly enough that in 2003, Mr. Myhrvold, who had left Microsoft but was close to Mr. Gates, contributed to Mr. Epstein’s 50th birthday book.
“A few years ago somebody at a party asked me, ‘Does Jeffrey Epstein manage your money?’” Mr. Myhrvold wrote in the book. “I replied, ‘No, but he advises me on lifestyle.’”
Mr. Myhrvold included images that he had taken on a trip to Africa and that he said “seemed more appropriate than anything I could put in words,” including photos of lions and zebras mating, and other wildlife in states of arousal.
Significantly, Mr. Myhrvold vouched for Mr. Epstein to Mr. Gates, who was debating meeting the financier for the first time, according to the documents. By December 2010, Mr. Gates had decided to meet Mr. Epstein and wrote to two employees of his private office that “Nathan had agreed with you that I would enjoy meeting with him and that it is a fine thing to do.”
Mr. Epstein also asked Mr. Myhrvold to set up a last-minute meeting with the other Microsoft co-founder, Paul Allen, when he was in the Seattle area in July 2011, though Mr. Myhrvold said he had not heard back from Mr. Allen. That December, Mr. Myhrvold wrote that he was boating by Mr. Epstein’s private Caribbean island.
Mr. Myhrvold and his spokeswoman did not respond to requests for comment. In the past, a representative has said Mr. Myhrvold knew Mr. Epstein through the scientific community and regretted meeting him.
In the early 2000s, Mr. Epstein leveraged his relationship with Melanie Walker, a woman he had recruited to model and whom he supported through medical school, to get further into Microsoft. Ms. Walker began dating Mr. Sinofsky and moved to Seattle to be with him. She started working at Mr. Gates’s foundation as a program officer in 2006.
There, Ms. Walker met Boris Nikolic, an adviser to the Gates Foundation who became a confidant of Mr. Epstein’s. Through Ms. Walker and Mr. Nikolic, Mr. Epstein kept close tabs on Mr. Gates, according to emails.
Mr. Nikolic said in an email that he regretted associating with Mr. Epstein, who “used lies to pursue his own agenda.” Ms. Walker did not respond to a request for comment.
Microsoft’s 2012 launch of its Windows 8 operating system, overseen by Mr. Sinofsky, was largely viewed as a failure. While Mr. Sinofsky had once been regarded as a candidate to lead Microsoft, he was planning to leave. Emails to Mr. Epstein from a sender whose name was redacted described Mr. Sinofsky as being miserable at the company because, the sender said, Mr. Ballmer stole credit for his work and Mr. Gates sided with Mr. Ballmer.
“He has no options or passions,” the sender wrote, adding, “What next?”
Mr. Sinofsky turned to Mr. Epstein for advice on his exit. He shared Microsoft’s proposed separation agreement and asked for Mr. Epstein’s opinion on the terms of his payout.
Mr. Sinofsky then shared nonpublic Microsoft information with Mr. Epstein, according to the documents. He forwarded Mr. Epstein an internal email from top executives discussing the poor sales of Microsoft’s Surface tablet.
Microsoft’s lawyers were “idiots” and “goofy,” Mr. Epstein wrote back. Mr. Sinofsky told Mr. Epstein that his goal was “to make them look petty, not me.” A confidant shared a private note from Mr. Gates bemoaning the “incompatibility” between Mr. Sinofsky and Mr. Ballmer.
After Mr. Sinofsky received a $14 million payout from Microsoft in 2013, he wrote to Mr. Epstein: “Got paid. You will be too :)”
Mr. Sinofsky declined to comment.
Mr. Epstein also forged a friendship with Mr. Hoffman, a co-founder of LinkedIn and a tech investor, that eventually led back to Microsoft. During a 2013 TED conference, Ms. Stone introduced Mr. Epstein via email to Joi Ito, the head of M.I.T.’s Media Lab, where Ms. Stone was an adviser and helped find funders. Mr. Ito connected Mr. Epstein to Mr. Hoffman.
In 2014, Mr. Epstein asked assistants to send Mr. Hoffman, Mr. Ito, Mr. Gates and Mr. Nikolic a gift: his signature half-zip sweatshirts, custom-made with the men’s initials embroidered in a diamond shape and an American flag patch sewn onto the sleeve.
That November, Mr. Hoffman and Mr. Ito spent a weekend on Mr. Epstein’s island, according to flight logs. Mr. Hoffman hopped on a jet arranged by Mr. Epstein later that week and traveled to New York, where he planned to stay at Mr. Epstein’s apartment and attend a breakfast party with Mr. Gates.
“Spoke to bill, he’s glad you are coming,” Mr. Epstein wrote to Mr. Hoffman.
Mr. Ito resigned from M.I.T. and several boards, including The New York Times Company’s, in 2019 after calling his relationship with Mr. Epstein an “error in judgment.”
In November 2014, Mr. Epstein sent Mr. Hoffman a gift of Hydro-Tone water weight dumbbells. Mr. Hoffman returned the favor, sending Mr. Epstein ice cream and “something that may strike your funny bone for the island,” which turned out to be a metal sculpture. He added that he would see Mr. Gates and Microsoft’s chief executive, Satya Nadella, in the new year.
In December 2014, Virginia Roberts Giuffre accused Mr. Epstein in court filings of trafficking her while she was underage, renewing media interest in Mr. Epstein’s crimes. Shortly after, Mr. Hoffman told Mr. Epstein that he had been thinking of ways to help with the negative media attention, though it was unclear if he was referring specifically to that case.
Knowing Mr. Hoffman offered Mr. Epstein new tech connections. After a 2015 dinner party in Palo Alto, Calif., attended by Elon Musk, Mark Zuckerberg, Peter Thiel and others, Mr. Epstein thanked Mr. Hoffman for the invitation and “his friendship.”
Mr. Hoffman later connected Mr. Epstein to Mr. Zuckerberg, Meta’s chief executive, over email “so that the conversation can continue.” There was no indication Mr. Zuckerberg replied.
In 2015, Mr. Epstein invited Mr. Hoffman to his island and ranch. He also nudged Mr. Hoffman to buy a private jet, advising him to make sure the pilots were married and nonmilitary.
“I will hold your hand all along the way,” Mr. Epstein said.
When Microsoft bought LinkedIn in 2016 for $26.2 billion, Mr. Epstein offered Mr. Hoffman his services in minimizing personal taxes. In 2017, Mr. Hoffman joined Microsoft’s board. He continued meeting with Mr. Epstein over Skype and updating him on his interactions with Mr. Gates through 2018. It is unclear what Mr. Hoffman and Mr. Epstein discussed.
Nicholas Kulish contributed reporting from New York.
Erin Griffith covers tech companies, start-ups and the culture of Silicon Valley from San Francisco.
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