Emails released by the US Justice Department show that Jeffrey Epstein played a role in connecting former Microsoft executive Steven Sinofsky with Apple CEO Tim Cook. The messages suggest Epstein not only advised Sinofsky after his exit from Microsoft, but also helped arrange introductions linked to possible future work at Apple.
According to documents made public (via The Verge) by the United States Department of Justice, the email trail dates back to late 2012, shortly after Sinofsky left Microsoft with a reported $14 million retirement package. During this period, Epstein discussed Sinofsky’s next career steps and mentioned outreach to major tech companies, including Apple and Samsung.
Epstein’s outreach to Apple leadership
In one email sent weeks after Sinofsky’s departure became public, Epstein told him that Tim Cook was “excited to meet.” However, Epstein added that Cook had heard Sinofsky might be starting a company with “farstall.” The spelling was unclear, but the reference appeared to point to Scott Forstall, who had left Apple a month earlier.
Despite the confusion, later emails indicate the meeting still happened. About six months later, Sinofsky confirmed to Epstein that he had spoken with Cook and described the conversation as serious.
“Cook asked if I am going to work. Then said we should stay in touch and talk if I want to work. It seemed pretty real.”
Steven Sinofsky, email to Jeffrey Epstein, May 29, 2013
Sinofsky also noted that a non-compete agreement prevented him from taking a full-time role immediately, but he wanted to stay in contact.
Other messages referencing Cook
Another email in the released set adds more context. It shows a message sent to Epstein by Ian Osborne, stating that he had recently met with Tim Cook.
“Will call this afternoon. Was with Tim Cook this morning.”
Ian Osborne, email to Jeffrey Epstein, February 5, 2013
Osborne’s email address was redacted, but the sender appears to be the British investor later linked to high-profile finance and technology deals. Separate court records previously showed Osborne and Epstein discussing efforts to influence senior banking appointments in the UK.
Apple’s response
Apple did not comment on the emails when contacted. The documents do not suggest wrongdoing by Apple or Tim Cook, but they show that Epstein actively sought access to senior technology executives and positioned himself as an intermediary during that period.
Overall, the emails highlight how Epstein inserted himself into private career discussions involving top tech leaders, including an apparent effort to connect Steven Sinofsky with Apple’s CEO.
