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Jeffrey Epstein Set Up Tim Cook Meeting for Ex-Windows Chief

Originally published on: February 3, 2026
▼ Summary

– Emails show former Microsoft executive Steven Sinofsky consulted Jeffrey Epstein for help securing his 2012 retirement package and future career moves at companies like Apple or Samsung.
– In one email, Epstein told Sinofsky that Apple CEO Tim Cook was “excited to meet,” but incorrectly suggested Sinofsky was starting a company with former Apple executive Scott Forstall.
– A later email exchange indicates Sinofsky did meet with Tim Cook, who told him they should talk when Sinofsky wanted to work full-time.
– Other released emails involve Epstein and British investor Ian Osborne discussing lobbying efforts to install “our friend” Jes Staley as Barclays CEO in 2012.
– The email correspondence, released by the Justice Department, reveals connections between Epstein and various high-profile business figures.

Newly released court documents reveal a surprising connection between a former Microsoft executive and the late financier Jeffrey Epstein, centering on an attempt to arrange a meeting with Apple CEO Tim Cook. The emails, part of a Justice Department disclosure, indicate that Steven Sinofsky, the former head of Microsoft’s Windows division, sought Epstein’s assistance not only in negotiating a multi-million dollar exit package but also in exploring new career opportunities at major tech firms following his 2012 departure.

One particular email, sent just weeks after Sinofsky’s exit was made public, shows Epstein writing to him with an update. Epstein claimed that Tim Cook was “excited to meet” with the former Windows chief. However, Epstein noted a potential complication, incorrectly stating that Cook had heard Sinofsky was starting a company with “farstall”, a misspelled reference to former Apple iOS chief Scott Forstall. Forstall had left Apple just one month prior, a detail Epstein seemed to have confused.

Despite this initial mix-up, a follow-up email from Sinofsky six months later confirms that a meeting with the Apple CEO did ultimately take place. Sinofsky recounted that Cook told him “we should talk when I want to work full time,” suggesting a professional dialogue about future employment possibilities. The correspondence places Epstein in the role of an intermediary, facilitating an introduction between a high-profile tech executive and one of the industry’s most powerful leaders.

Further context emerges from another email exchange included in the release, this one between Epstein and a contact named Ian Osborne. In the message, Osborne states, “Will call this afternoon. Was with Tim Cook this morning.” While the email address is redacted, the recipient is believed to be British investor Ian Osborne, known at the time as a liaison for wealthy individuals. Previous reporting has connected Osborne and Epstein, noting their collaboration in 2012 on efforts to influence the appointment of a new CEO at Barclays bank.

Apple has not provided any comment on the correspondence or the alleged meeting. The documents add another layer to the complex web of Epstein’s associations, illustrating how his network extended into the upper echelons of the technology sector, where he apparently acted as a connector for executives navigating career transitions.

(Source: The Verge)

Topics

jeffrey epstein 95% steven sinofsky 95% email evidence 90% apple ceo 85% career consultation 85% tech industry 80% ian osborne 80% corporate lobbying 75% scott forstall 75% executive departures 70%