Emails between former Windows boss Steven Sinofsky and Jeffrey Epstein published by the Justice Department on Friday show that Sinofsky constantly sought Epstein’s advice while negotiating his sudden exit from Microsoft in November 2012, with emails forwarded to him in almost real time as the negotiations progressed. According to the emails, it appears that Sinofsky paid Epstein for his help at the end of the process, and turned to him for assistance in finding a new job with Apple or Samsung.
One series revealed that Sinofsky sent Epstein a confidential email between Microsoft executives in July 2013 detailing issues surrounding the launch of the Surface, warning that the Surface RT tablet was “going to fail catastrophically in public.” Sinofsky originally sent an email to former Microsoft CEO Steve Ballmer on November 3, 2012, describing how Surface RT sales were in a “very difficult situation” and that the company may be “on the verge of an unmarketable situation.” Sinofsky left Microsoft just days after his correspondence with Ballmer.
Microsoft had bet big on the Surface RT tablet, its Arm-powered competitor to the iPad, and Windows 8’s new touch-focused UI, and expected 70 percent of Surface RT sales to be online. Instead, Microsoft faced “significant problems” selling its tablets online, and made far more units than it was able to sell, according to Sinofsky’s email.
The email to Epstein also reveals that Sinofsky plans to broaden Microsoft’s retail footprint outside the US based on data suggesting people want to play with the Surface in a store before making a purchase. The plan surprised both Ballmer and former Microsoft Chief Operating Officer Kevin Turner. After rambling for several days about Surface RT sales issues, Microsoft announced Sinofsky’s departure a week later – less than a month after the Windows 8 and Microsoft Surface launches.
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.
According to several emails sent to Epstein, Sinofsky turned to Epstein for help in negotiating an exit package from Microsoft and spent several months negotiating a $14 million “retirement” package. It is unclear why Sinofsky turned to Epstein for advice four years after Epstein was accused of sex trafficking of minors. The pair 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 advisor in 1998, before joining the Gates Foundation in 2006.
I reached out to Steven Sinofsky for comment about why he sought advice from a registered sex offender, and after initially declining to comment on the record he referred 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 VergeThe strict policy requiring communications professionals to remain on the record also declined to comment on the record.
Microsoft also declined to comment.
According to the emails, in the weeks after Sinofsky left Microsoft, someone with the nickname “Poops” warned Epstein that Sinofsky had “sent several mails saying he was 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 troubled by questions about his possible dismissal. Months later, in an email to Epstein, Sinofsky was also concerned about his Microsoft settlement, which made it seem like he was fired.
Microsoft initially offered Sinofsky $5 million for a non-compete deal, but the company was willing to pay even more than $5 million if Sinofsky agreed that he would “not 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 prevent Sinofsky from writing “any information about Microsoft that he deems offensive.”
Epstein advised Sinofsky to continue pushing for a $20 million settlement, which led to several months of back-and-forth until Microsoft finally settled on a $14 million settlement in July 2013. In the months before, Sinofsky had also speculated that Microsoft was concerned about recruiting his fellow Windows employees, or that Ballmer was blaming Windows 8 on him. According to the emails, at one point in May 2013, Sinofsky told Epstein that Microsoft was calling reporters asking if they had talked to him recently.
In the months before the final Microsoft settlement, Sinofsky and Epstein apparently exchanged emails, conducted numerous calls, and met for meetings, dinners, and lunches. Sinofsky also shared details of meeting with Samsung and Apple CEO Tim Cook for the potential job role. According to the Sinofsky email sent to Epstein, one of the Samsung meetings was related to the Android phone maker wanting to “build software to compete and not rely on Google”. Sinofsky was concerned that Samsung was talking to Ballmer, but ultimately the deal never happened.
Epstein also appears to have arranged a meeting between Tim Cook and Sinofsky, but Cook was initially concerned that Sinofsky was starting a company with Scott Forstall, the former Apple executive who was ousted after the Apple Maps failure. The pair eventually spoke in May 2013 and agreed to stay in touch about potential opportunities at Apple.
According to the emails, the back-and-forth over Sinofsky’s Microsoft settlement infuriated both parties. Microsoft was not happy with Sinofsky’s blog posts before the settlement, and in an email sent to Epstein in June 2013, Sinofsky described Microsoft’s behavior as “crazy” and the possibility of “getting even crazier.” Sinofsky was also keen to be able to talk about his time at Microsoft, and sought Epstein’s advice on questions from journalists.
Once the Microsoft settlement was finalized and publicly announced on July 3, 2013, Sinofsky described herself as his “good ex-wife” in an email to Epstein. Microsoft transferred the money to Sinofsky several months later, and Sinofsky said in an email to Epstein in September 2013, “Got the payment. You’ll get it too :)”.
Shortly after Sinofsky’s settlement was announced, Microsoft announced a $900 million writedown on the Surface RT in July 2013. The loss was caused by an “inventory adjustment”, when Microsoft reportedly made 3 to 5 million Surface tablets in the holiday quarter, but reportedly sold just over 1 million Surface RT devices.
Epstein and Sinofsky continued to discuss the tech industry, hold meetups and more until at least 2017 — two years before Epstein was charged with sex trafficking of minors in 2019. Sinofsky was particularly interested in Ballmer’s retirement from Microsoft and a stockholder revolt in 2013. He also contacted Epstein to help his former colleagues at Microsoft connect with Steven Hawking for an advertisement. Microsoft finally aired an ad in the Super Bowl in 2014, without Steven Hawking.
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