Epstein Charged a Microsoft Executive $1 Million to Coach His Exit Negotiation

When Richard Kahn, Jeffrey Epstein's longtime accountant, sat for a closed-door deposition before the House Oversight Committee in March 2026, he made a disclosure that has received remarkably little attention. Under oath, Kahn named Epstein's five clients: Les Wexner, Glenn Dubin, Leon Black, the Rothschilds -- and Steven Sinofsky, the former president of Microsoft's Windows division.

The first four names have been exhaustively reported. Wexner's decades-long financial entanglement with Epstein has been the subject of multiple investigations. Dubin's social ties have been picked apart in the press. Leon Black paid Epstein $158 million in advisory fees. The Rothschild connection has generated its own cottage industry of reporting. But Sinofsky -- the fifth name -- has barely registered in media coverage.

A review of 2,604 documents in the EFTA corpus tells a story that has never been publicly reported: Epstein didn't just advise Sinofsky. He ran his entire exit negotiation from Microsoft, charged a $1 million fee for it, and then turned Sinofsky into a pipeline for Silicon Valley intelligence that lasted the better part of a decade.

Before the Exit: Sinofsky in Epstein's Calendar

The relationship predates Sinofsky's departure from Microsoft. In September 2011 -- more than a year before the Windows 8 crisis -- Epstein told his assistant Lesley Groff: "add regina to 17th week, as well as sinofsky, melanie." Groff, apparently unfamiliar with the name, asked to confirm: "do you mean 'sinofsky' or Risovsky."

That same month, Cecile de Jongh -- the wife of John de Jongh Jr., then-governor of the U.S. Virgin Islands -- emailed Epstein asking for "any contact information for Steve Sinofsky. I see that he works at Microsoft." Epstein provided the contact. The governor's wife was using Epstein as a broker to reach a sitting Microsoft executive. By 2011, Sinofsky was already embedded in Epstein's network -- scheduled in his calendar, passed between his contacts, connected to the political apparatus of the USVI that Epstein had cultivated for years.

The $1 Million Fee

In November 2012, Sinofsky was pushed out of Microsoft following the troubled launch of Windows 8. Within weeks, he was forwarding Microsoft's legal correspondence directly to Epstein.

"They are making this too one sided... they never got to $20 and are asking for more," Sinofsky wrote to Epstein in December 2012, referring to approximately $20 million in stock vesting at stake. Epstein's response was immediate: "this negoatiation needs to be face to face."

By January 2013, Epstein was personally coaching Sinofsky's strategy in granular detail. "Have jay just hang tough," Epstein wrote, referring to Sinofsky's attorney Jay Lefkowitz at Kirkland & Ellis. "They get quiet for 20. They get peace for 20. Only at the very last minute should you move... use the fiscal cliff as a model. When jay asks what do you really want, tell him twenty, do not give up your hand to anyone."

The "twenty" was $20 million in stock awards -- 55,159 shares per vesting period, according to Rule 408 settlement correspondence between Lefkowitz and Microsoft's Chief Legal Officer Brad Smith that appears in the EFTA files.

In April 2013, Epstein made his fee explicit: "I will charge you a one million dollar fee (I will not get insulted if you choose not to). Right at the end, not for jay, I will attempt to specifically get samsung approved."

Sinofsky's response was unequivocal: "Any fee you want is fine. That isn't an issue for me at all. Or if you don't want to be involved that is fine too. I would rather be friends more than anything."

The Wire to Kahn

The financial trail leads directly to the man who named Sinofsky as a client. In August 2013, Epstein asked Sinofsky to pay his invoice: "by the way, I assume you will pay my invoice when you get paid in sept?"

The following month, a Citibank banker named Shiji Chacko confirmed a wire transfer was "completed" with a Federal Reserve reference number. Epstein forwarded that confirmation directly to Richard Kahn -- the same accountant who, 13 years later, would name Sinofsky as one of five clients under oath.

The Samsung Channel and the Bill Gates Question

After leaving Microsoft, Sinofsky was offered roles at Samsung and Andreessen Horowitz. He told Epstein about the Samsung opportunity. Epstein's reply was revealing: "i never discuss with bill until after negotiations are finished, lets talk about samsung later today."

The implication is striking. Epstein was managing a separate channel to Bill Gates regarding Sinofsky's career moves -- and was careful about the sequencing. He didn't want Gates to know about Samsung until the deal was locked. This suggests Epstein positioned himself as an intermediary between the two Microsoft figures, controlling information flow in both directions.

Sinofsky also fed Epstein intelligence about Gates directly. He told Epstein that "Larry Cohen at bgc3 spontaneously volunteered that bill didn't say anything about me at Samsung." He later told Epstein he was "bringing bill to meet folks at andreessen horowitz in 3 weeks" -- facilitating a Gates-a16z introduction through Epstein's network.

The Intelligence Pipeline

As a board partner at Andreessen Horowitz, Sinofsky became a window into one of Silicon Valley's most influential venture capital firms. The relationship with Epstein didn't end with the Microsoft negotiation. It deepened.

In May 2013, Sinofsky reported a conversation with Apple's CEO to Epstein: "Good talk with tim. He said we should talk when I want to work full time. Told him about Andreessen and winding down non compete."

In November 2013, Sinofsky told Epstein about Bitcoin: "I'm up 50% on my BTC investment!" The detail is minor on its own, but it illustrates the texture of the relationship -- Sinofsky was sharing personal financial updates with Epstein as a matter of course, treating him as a confidant.

By December 2014, Epstein was pushing for direct access to Andreessen Horowitz's deal flow. "Can you ask??" Epstein wrote. Sinofsky pushed back: "It would be awkward to share. It isn't my company. Pro rata rounds are not usually discussed as a whole team."

In February 2013, a figure named Benny Shabtai was scheduled for an "evening with Steve Sinofsky" -- suggesting Epstein was arranging introductions around Sinofsky as a social asset, packaging access to the former Microsoft executive for others in his orbit.

In October 2017, Sinofsky sent Epstein a WeWork article. The following month, Epstein cc'd Sinofsky on emails with Masha Drokova of Day One Ventures about a health-tech startup -- pulling Sinofsky into Epstein's venture deal-making as a technical validator. In 2018, Sinofsky forwarded Axios Pro Rata newsletters about gender bias in venture funding.

The Wider Network

Sinofsky's name didn't exist in isolation in Epstein's files. It appears in a web of connections that reveals how Epstein traded on his access.

In Epstein's handwritten Apple Notes -- recovered from a device seized by investigators -- Sinofsky appears alongside notations including "Putin, karp? wealth" and references to Ghislaine Maxwell, Ian Osborne, and Leon Black. These are not formal documents. They are the private jottings of a man cataloging his assets.

Ian Osborne, a British political operative who served as a frequent Epstein intermediary, discussed placing Sinofsky in meetings with Peter Thiel, Reid Hoffman, and Drew Houston -- the founder of Dropbox. The implication is that Sinofsky was being routed through Epstein's network not just as a client, but as a commodity: a former top Microsoft executive whose access and credibility could be deployed.

In 2016, they met in person at 1 Letterman Drive in San Francisco's Presidio.

Still on the List in 2019

The documents show the relationship was active until just weeks before Epstein's arrest. In June 2019, Sinofsky appeared on a contact list Epstein prepared for Steve Bannon, alongside Bill Gates, Peter Thiel, Reid Hoffman, Prince Andrew, Bill Clinton, and Alan Dershowitz.

Eight years after Lesley Groff first asked how to spell his name, Sinofsky was still in the Rolodex -- still useful, still connected, still listed alongside the most powerful names in Epstein's world.

What It Means

The Sinofsky files reveal something broader about how Epstein operated. He didn't just socialize with powerful people. He provided a specific, documented service -- high-stakes negotiation coaching -- and charged a specific price. He managed the lawyer. He dictated the strategy. He collected the fee through his accountant. And then he leveraged the relationship for years of access to exactly the kind of deal flow and intelligence that made him valuable to his other clients.

Sinofsky has not publicly commented on his relationship with Epstein. Microsoft declined to comment on the exit negotiation. Kahn's testimony naming Sinofsky as a client has not been challenged.

The 2,604 documents spanning eight years tell a story of a relationship that was not casual, not incidental, and not limited to a few social encounters. It was a paid, professional engagement between a convicted sex offender and a top technology executive -- one that produced a paper trail more extensive than almost any other client relationship in the Epstein files.

All documents referenced in this article are available in the EFTA document archive. Person profiles: Steven Sinofsky, Richard Kahn, Jeffrey Epstein.