Former Windows 8 boss recruited Epstein to help negotiate his messy Microsoft exit

Emails between former Windows boss Steven Sinofsky and Jeffrey Epstein, published by the Justice Department on Friday, appear to show that Sinofsky constantly sought Epstein’s advice as he negotiated his surprise exit from Microsoft in November 2012, forwarding emails to him in nearly real time as talks progressed. Sinofsky also appears to have paid Epstein for his help at the end of the process, and turned to him for assistance finding a new job with Apple or Samsung, according to the emails.

One chain appears to show that Sinofsky forwarded a confidential email between Microsoft executives to Epstein in July 2013 that details the issues around the launch of Surface, warning that the Surface RT tablet was “about to catastrophically fail in a very public way.” Sinofsky had originally sent the email to former Microsoft CEO Steve Ballmer on November 3rd, 2012, detailing how Surface RT sales were in a “very tough spot” and that the company might be on “the verge of an unrecoverable situation.” Sinofsky left Microsoft just days after the correspondence with Ballmer.

Microsoft had bet on the Surface RT tablet, its Arm-powered competitor to the iPad, and Windows 8’s new touch-focused UI in a big way, and had expected 70 percent of Surface RT sales to be made online. Instead, Microsoft faced “significant problems” selling its tablet online, according to the email from Sinofsky, and had made far more units than it was able to sell.

The email to Epstein also appears to show that Sinofsky pitched a plan to broaden Microsoft’s retail footprint outside the US, based on data that suggested people wanted to play with a Surface in a store before committing to a purchase. This plan surprised both Ballmer and Kevin Turner, Microsoft’s former chief operating officer. After days of back-and-forth about the Surface RT sales issues, Microsoft announced Sinofsky’s departure a week later — less than a month after the Windows 8 and Microsoft Surface launch.

At the time, we reported that a clash of personalities led to Sinofsky’s departure, but the Epstein files point to what looks like a messy firing that dragged on for months.

Sinofsky turned to Epstein to help barter an exit package from Microsoft, and spent months negotiating a $14 million “retirement” package, according to multiple emails to Epstein. It’s not clear why Sinofsky turned to Epstein for advice, four years after Epstein was charged with sex trafficking minors. The pair had discussed Internet Explorer 9 in 2011, while Sinofsky was still at Microsoft, and his longtime partner, Dr. Melanie S. Walker, also worked for Epstein as his science adviser in 1998, before joining the Gates Foundation in 2006.

I reached out to Steven Sinofsky for comment on why he sought advice from a registered sex offender, and after initially refusing to comment on the record he directed me to Matthew Hiltzik at Hiltzik Strategies, a communications firm that specializes in crisis management. Hiltzik asked to speak on background, and when told about The Verge’s strict policy requiring communications professionals to be on the record, also declined to comment on the record.

Microsoft also declined to comment.

According to the emails, in the weeks after Sinofsky’s Microsoft departure, someone nicknamed “poops” warned Epstein that Sinofsky had “sent several mails that he is going to kill himself,” after news of his work as a Harvard Business School teacher raised further questions about the nature of his Microsoft exit. Sinofsky seemed upset about questions around his potential firing. Months later, in an email to Epstein, Sinofsky was also concerned about his Microsoft settlement making it look like he was fired.

Microsoft initially offered $5 million to Sinofsky for a noncompete deal, but the company was willing to pay even more than $5 million if Sinofsky agreed that he wouldn’t “communicate with Microsoft employees regarding compensation, business strategy, and certain other matters,” according to an email from Scott D. Price, an executive compensation lawyer hired by Sinofsky. The email also said that Microsoft wanted to stop Sinofsky from ever authoring “any information regarding Microsoft that they consider unpleasant.”

Epstein advised Sinofsky to keep pushing for a $20 million settlement, which led to months of back-and-forth until Microsoft eventually settled on the $14 million sum in July 2013. In the months before that, Sinofsky also speculated Microsoft was worried about him recruiting fellow Windows employees, and that Ballmer was blaming Windows 8 on him. At one point in May 2013, according to the emails, Sinofsky told Epstein that Microsoft had been calling reporters asking if they’d spoken to him recently.

In the months leading up to the finalized Microsoft settlement, Sinofsky and Epstein apparently exchanged emails, organized multiple calls, and met for meetings, dinners, and lunches. Sinofsky even shared details of meeting with Samsung for a potential job, and Apple CEO Tim Cook. One of the Samsung meetings was related to the Android phone maker wanting to “do software to compete and not rely on Google,” according to a Sinofsky email to Epstein. Sinofsky was worried about Samsung talking to Ballmer, but ultimately the job never worked out.

Epstein also appears to have arranged a meeting between Tim Cook and Sinofsky, but Cook initially appeared to be concerned that Sinofsky was starting a company with Scott Forstall, the former Apple executive that was ousted after the failure of Apple Maps. The pair eventually talked in May 2013, and agreed to stay in touch about potential Apple opportunities.

According to the emails, the back-and-forth of Sinofsky’s Microsoft settlement agitated both sides. Microsoft was not happy with Sinofsky’s blog posts ahead of the settlement, and Sinofsky described Microsoft’s behavior as “crazy” and likely to “get more crazy” in a June 2013 email to Epstein. Sinofsky was also keen to be able to talk about his time at Microsoft, and sought Epstein’s advice on questions from reporters.

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

Microsoft went on to announce a $900 million writedown on Surface RT in July 2013, just after announcing Sinofsky’s settlement. The loss was all down to “inventory adjustments,” after Microsoft had reportedly built 3 to 5 million Surface tablets in the holiday quarter but reportedly only sold just over 1 million Surface RT devices.

Epstein and Sinofsky continued to discuss the tech industry, organize meetups, and more until at least 2017 — two years before Epstein was charged with the sex trafficking of minors in 2019. Sinofsky seemed particularly interested in Ballmer retiring from Microsoft, and a stockholder revolt in 2013. He even approached Epstein to help his former colleagues at Microsoft try and connect with Stephen Hawking for a commercial. Microsoft eventually aired the commercial at the Super Bowl in 2014, without Stephen Hawking.