"The trigger was the Surface RT, Microsoft's first real attempt to muscle into Apple's hardware turf. By November 2012, Sinofsky was warning internally that it was going sideways fast. In an email to CEO Steve Ballmer and COO Kevin Turner, he said the device was "about to catastrophically fail in a very public way," with sales tracking at roughly one-tenth of even the lowest expectations."
"What followed was a series of practical, unsentimental emails about money and constraints. Sinofsky sent Epstein his full retirement agreement, complaining that Microsoft was fixated on restrictive non-competes and reluctant to grant full vesting of stock awards. Unsure what leverage he still had, he asked outright. Epstein's answer was clear and repeated across messages: ask for $20 million and don't budge. "Just repeat 20," Epstein advised. "Do not let [them] talk you down.""
Sinofsky warned that the Surface RT was failing and that sales were tracking at roughly one-tenth of expectations, predicting a very public collapse. He emailed CEO Steve Ballmer and COO Kevin Turner about the dire trajectory, and left Microsoft nine days later. Sinofsky later forwarded the email chain to Jeffrey Epstein and noted Microsoft ultimately wrote off $900 million in unsold Surface inventory. He exchanged practical emails with Epstein about his retirement agreement, restrictive non-competes, and unvested stock awards. Epstein repeatedly advised asking for $20 million; Sinofsky departed with about $14 million in stock. There is no suggestion of criminal behavior by Sinofsky.
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