Ex-Windows 8 Chief Enlists Epstein for Complicated Microsoft Departure Negotiations

Emails between former Windows chief Steven Sinofsky and Jeffrey Epstein, released by the Justice Department, reveal that Sinofsky frequently sought Epstein’s counsel during his unexpected departure from Microsoft in November 2012. He forwarded emails to Epstein almost in real time as negotiations unfolded, and it seems he compensated Epstein for his assistance, including help in securing a new position at Apple or Samsung.

One email chain indicates that Sinofsky shared a confidential message from Microsoft executives with Epstein in July 2013, highlighting concerns about the Surface RT tablet, which was “about to catastrophically fail in a very public way.” This email, originally sent to former Microsoft CEO Steve Ballmer on November 3, 2012, outlined the dire sales situation for Surface RT, suggesting the company was nearing an “unrecoverable situation.” Sinofsky’s exit from Microsoft came just days after this exchange with Ballmer.

Microsoft had heavily invested in the Surface RT tablet, its Arm-powered rival to the iPad, banking on a new touch-centric UI with Windows 8 and anticipating that 70 percent of Surface RT sales would occur online. However, the reality was starkly different, as Sinofsky noted significant challenges in online sales and an oversupply of units.

The email to Epstein also reveals Sinofsky’s proposal to expand Microsoft’s retail presence beyond the U.S., based on insights that customers preferred to interact with a Surface device in-store before making a purchase. This idea caught both Ballmer and Kevin Turner, the former COO, off guard. After several discussions about the Surface RT sales troubles, Microsoft announced Sinofsky’s departure a week later, shortly after the Windows 8 and Surface launch.

Initially, it was reported that personality clashes contributed to Sinofsky’s exit, but the emails suggest a more complicated and prolonged dismissal process. Sinofsky sought Epstein’s help in negotiating a $14 million exit package, as indicated in multiple emails. It remains unclear why he turned to Epstein for guidance, especially given Epstein’s legal troubles from four years prior. The two had previously discussed Internet Explorer 9 in 2011, and Sinofsky’s partner had worked for Epstein in the late ’90s.

When approached for comment about his choice to consult a registered sex offender, Sinofsky initially declined but later referred inquiries to a crisis management firm, which also chose not to comment on the record. Microsoft similarly opted not to provide any statements.

In the weeks following Sinofsky’s exit, someone using the nickname “poops” alerted Epstein that Sinofsky had sent several alarming emails indicating suicidal thoughts, particularly as his new role as a Harvard Business School teacher raised further scrutiny about his departure from Microsoft. Sinofsky expressed frustration over speculation regarding his firing. Later, he worried that his settlement with Microsoft might imply he was terminated.

Microsoft initially proposed a $5 million noncompete agreement, but was willing to increase that amount if Sinofsky agreed not to discuss certain topics with Microsoft employees. An email from an executive compensation lawyer revealed that Microsoft aimed to prevent Sinofsky from publishing any negative information about the company.

Epstein encouraged Sinofsky to push for a $20 million settlement, leading to extensive negotiations that ultimately resulted in the $14 million agreement in July 2013. During this time, Sinofsky speculated that Microsoft was concerned about him recruiting former Windows colleagues and that Ballmer was attributing the Windows 8 issues to him. In May 2013, Sinofsky mentioned that Microsoft had been contacting reporters to inquire about his recent communications.

As the settlement discussions progressed, Sinofsky and Epstein exchanged numerous emails, held calls, and met for meals. Sinofsky shared details about potential job opportunities with Samsung and Apple, including a meeting where Samsung expressed interest in developing software independent of Google. Although Sinofsky was anxious about Samsung’s interactions with Ballmer, the job opportunity ultimately did not materialize.

Epstein also seemed to facilitate a meeting between Sinofsky and Apple CEO Tim Cook, although Cook initially expressed concerns about Sinofsky potentially starting a company with Scott Forstall, a former Apple executive. They eventually connected in May 2013 and agreed to keep in touch regarding future opportunities at Apple.

The ongoing negotiations for Sinofsky’s settlement created tension on both sides. Microsoft was displeased with Sinofsky’s blog posts leading up to the settlement, while Sinofsky described Microsoft’s actions as “crazy” in a June 2013 email. He was eager to discuss his experiences at Microsoft and sought Epstein’s advice on how to handle inquiries from the press.

Once the settlement was finalized and publicly announced on July 3, 2013, Sinofsky humorously referred to himself as a “good ex-wife” in an email to Epstein. Microsoft transferred the settlement funds to Sinofsky several months later, and he informed Epstein, “Got paid. You will be too :)” in a September 2013 email.

Shortly after announcing Sinofsky’s settlement, Microsoft reported a $900 million writedown on Surface RT due to “inventory adjustments,” having produced 3 to 5 million Surface tablets but only selling just over 1 million units.

Sinofsky and Epstein continued to discuss the tech landscape and arrange meetings until at least 2017, two years before Epstein faced charges for sex trafficking minors in 2019. Sinofsky showed particular interest in Ballmer’s retirement from Microsoft and a stockholder revolt in 2013. He even sought Epstein’s help in connecting his former Microsoft colleagues with Stephen Hawking for a commercial, which ultimately aired during the Super Bowl in 2014, albeit without Hawking.