Former Windows chief shared internal secrets with Jeffrey Epstein, documents reveal

Among millions of pages released by the Department of Justice in recent days related to Jeffrey Epstein, there’s a correspondence that’s particularly interesting to the Windows community. Steven Sinofsky, Microsoft's former Windows chief, was in extensive contact with the convicted sex offender.

The documents reveal Sinofsky shared confidential internal company information, sought Epstein's counsel on his departure from Microsoft, and was advised by the financier to seek a $20 million retirement package.

A July 18, 2013 email shows Sinofsky forwarding an extensive thread of internal Microsoft emails to Epstein. In the thread, Sinofsky mentions the troubled launch of Microsoft's Surface tablet and a disagreement with then Microsoft CEO, Steve Ballmer, on how to recover from it.

"MS wrote off 900M on inventory...this is a mail thread from November saying this will happen," Sinofsky wrote to Epstein. "Even better--at the last minute this 900M was an increase over the 'planned' write off. Classic 'well it is bad news so let's bank some of it'..."

The emails contain sensitive internal information, such as real-time sales data, manufacturing projections, and retailer margin structures. The forwarded correspondence happened between CEO Steve Ballmer, COO Kevin Turner, and Sinofsky himself in November 2012.

Additional released documents show this wasn’t an isolated case. Sinofsky apparently sought Epstein's advice regarding his retirement from Microsoft, with Epstein advising him to pursue a $20 million retirement plan. Why a departing Microsoft executive sought counsel from Epstein remains unclear.

Sinofsky was one of Microsoft's most powerful executives and a potential CEO successor before his sudden departure in November 2012. Microsoft officially described Sinofsky’s departure as “stepping down,” but it was widely viewed as a dismissal at the time. It’s also unclear whether Sinofsky’s connection with Epstein played any part.

Sinofsky was head of Windows at the time of the Surface RT release, which was one of Microsoft’s biggest hardware failures in the company’s history. The rocky start of the Surface RT tablet contributed to Microsoft’s first quarterly loss as a public company.

Epstein cultivated relationships with prominent figures across technology, science, and business. Harvard professor Martin Nowak described him in 2003 as "one of the most pleasant philanthropists to deal with" and a man who "supports science without any conditions,” further saying that “there are not any disadvantages to associating with him.” This reputation helped Epstein gain access to executives like Sinofsky despite his criminal history.

Neither Sinofsky nor Microsoft have officially responded to the release of these emails.