Who is Steven Sinofsky in the Epstein files?

Steven Sinofsky is the former president of Microsoft's Windows Division who oversaw the development of Windows 7 and Windows 8. The Epstein files reveal a substantive personal and advisory relationship between Sinofsky and Epstein spanning from at least 2011 to 2018. Sinofsky shared confidential Microsoft internal emails with Epstein, used him as an advisor to negotiate his exit from Microsoft after the Surface RT debacle, and maintained regular correspondence about technology industry developments, career prospects, and social events.

What confidential Microsoft information did Sinofsky share with Epstein?

According to documents released by the Department of Justice, Sinofsky forwarded to Epstein a confidential email exchange between himself, then-CEO Steve Ballmer, and then-COO Kevin Turner from November 2012. The emails revealed the internal panic as Microsoft leadership realized the Surface RT tablet was failing catastrophically—Sinofsky wrote that it was 'about to catastrophically fail in a very public way' and that they didn't know how to explain selling only a tenth of expected devices. Microsoft later wrote off approximately $900 million in unsold Surface RT inventory. Sinofsky also shared his draft retirement agreement with Epstein for guidance.

Did Epstein help Sinofsky negotiate his Microsoft exit?

Yes. After Sinofsky departed Microsoft in November 2012, he turned to Epstein for advice on his retirement package. Emails show Sinofsky forwarding his draft retirement agreement to Epstein and discussing strategy. Epstein reportedly advised Sinofsky to seek a $20 million retirement package. Sinofsky ultimately settled for approximately $14 million in stock, with the agreement finalized in mid-2013. Their correspondence about the exit continued for months, with Sinofsky thanking Epstein for his help.

Did Epstein arrange a meeting between Sinofsky and Tim Cook?

The Epstein files indicate that Epstein attempted to broker a connection between Sinofsky and Apple CEO Tim Cook after Sinofsky's departure from Microsoft. Emails from late 2012 suggest Epstein referenced having spoken with Cook about a potential meeting regarding job opportunities for Sinofsky. Later correspondence indicates the meeting did take place, with Sinofsky confirming to Epstein approximately six months later that he had spoken with Cook.

How long did the Sinofsky-Epstein relationship last?

The documents show a relationship spanning at least seven years, from 2011 through 2018. The earliest correspondence includes a 2011 email where Sinofsky forwarded an article about 'Atlas Shrugged' to Epstein associate Melanie Walker. Their communication continued through his Microsoft exit negotiations in 2012-2013, ongoing personal exchanges through 2016, and as late as February 2018 when Sinofsky forwarded a newsletter to Epstein. The breadth and casual tone of the correspondence suggests a genuine personal relationship rather than a transactional one.

Who is Steven Sinofsky in the Epstein files?

Steven Sinofsky is the former president of Microsoft's Windows Division who oversaw the development of Windows 7 and Windows 8. The Epstein files reveal a substantive personal and advisory relationship between Sinofsky and Epstein spanning from at least 2011 to 2018. Sinofsky shared confidential Microsoft internal emails with Epstein, used him as an advisor to negotiate his exit from Microsoft after the Surface RT debacle, and maintained regular correspondence about technology industry developments, career prospects, and social events.

What confidential Microsoft information did Sinofsky share with Epstein?

According to documents released by the Department of Justice, Sinofsky forwarded to Epstein a confidential email exchange between himself, then-CEO Steve Ballmer, and then-COO Kevin Turner from November 2012. The emails revealed the internal panic as Microsoft leadership realized the Surface RT tablet was failing catastrophically—Sinofsky wrote that it was 'about to catastrophically fail in a very public way' and that they didn't know how to explain selling only a tenth of expected devices. Microsoft later wrote off approximately $900 million in unsold Surface RT inventory. Sinofsky also shared his draft retirement agreement with Epstein for guidance.

Did Epstein help Sinofsky negotiate his Microsoft exit?

Yes. After Sinofsky departed Microsoft in November 2012, he turned to Epstein for advice on his retirement package. Emails show Sinofsky forwarding his draft retirement agreement to Epstein and discussing strategy. Epstein reportedly advised Sinofsky to seek a $20 million retirement package. Sinofsky ultimately settled for approximately $14 million in stock, with the agreement finalized in mid-2013. Their correspondence about the exit continued for months, with Sinofsky thanking Epstein for his help.

Did Epstein arrange a meeting between Sinofsky and Tim Cook?

The Epstein files indicate that Epstein attempted to broker a connection between Sinofsky and Apple CEO Tim Cook after Sinofsky's departure from Microsoft. Emails from late 2012 suggest Epstein referenced having spoken with Cook about a potential meeting regarding job opportunities for Sinofsky. Later correspondence indicates the meeting did take place, with Sinofsky confirming to Epstein approximately six months later that he had spoken with Cook.

How long did the Sinofsky-Epstein relationship last?

The documents show a relationship spanning at least seven years, from 2011 through 2018. The earliest correspondence includes a 2011 email where Sinofsky forwarded an article about 'Atlas Shrugged' to Epstein associate Melanie Walker. Their communication continued through his Microsoft exit negotiations in 2012-2013, ongoing personal exchanges through 2016, and as late as February 2018 when Sinofsky forwarded a newsletter to Epstein. The breadth and casual tone of the correspondence suggests a genuine personal relationship rather than a transactional one.

Back to People & Entities

Steven Sinofsky

Person

642

Total Mentions

599

Documents

455

Connected Entities

American businessman, former Microsoft engineer

Wikipedia IMDb X/Twitter LinkedIn Official Site

Steven Sinofsky, former president of Microsoft's Windows Division, had a substantive personal and advisory relationship with Jeffrey Epstein spanning at least 2011 to 2018, using Epstein as a confidant for career strategy, sharing confidential Microsoft internal emails, and seeking his help negotiating a retirement package after leaving the company.

Sinofsky appears extensively in personal email correspondence directly with Epstein, making this one of the more substantive connections in the files. The emails reveal Sinofsky shared confidential Microsoft internal communications with Epstein—including a panicked exchange between himself, CEO Steve Ballmer, and COO Kevin Turner about the imminent failure of Surface RT—and sought Epstein's advice on negotiating his Microsoft exit, with Epstein reportedly suggesting he seek a $20 million retirement package. Sinofsky also discussed meeting Apple CEO Tim Cook through Epstein's network, and exchanged casual messages about technology industry news, social events, and personal matters through at least February 2018. He also communicated with Epstein associate Lesley Groff and was connected to Boris Nikolic through Epstein.

Key Highlights

•Shared confidential Microsoft internal emails with Epstein, including a crisis exchange about Surface RT's impending failure where Sinofsky wrote 'Surface is about to catastrophically fail in a very public way'
•Used Epstein as a career advisor to negotiate his Microsoft retirement package—Epstein reportedly advised seeking $20 million; Sinofsky ultimately received approximately $14 million in stock
•Epstein brokered a connection to Apple CEO Tim Cook for Sinofsky, with emails indicating the meeting did take place
•Relationship spanned at least 2011 to 2018, with emails covering technology industry analysis, personal matters, and social events
•Also corresponded with Epstein's assistant Lesley Groff and was connected to Epstein associate Boris Nikolic

Frequently Asked Questions

Books for Further Reading

Perversion of Justice: The Jeffrey Epstein Story

Julie K. Brown

Investigative journalism that broke the Epstein case open

Filthy Rich: The Jeffrey Epstein Story

James Patterson

Bestselling account of Epstein's crimes and network

Relentless Pursuit: My Fight for the Victims of Jeffrey Epstein

Bradley J. Edwards

Victims' attorney's firsthand account

Document Mentions (20 of 599)

EFTA00395402.pdf

EFTA00395402

2 mentions

Thank you. the staff line...or you may call M, Jeffrey's From: Sent: 2/19/2013 11:42 AM To: Subject: Jeffrey Epstein Hi ...I understand Steve (Sinofsky) will be coming to see Jeffrey tonight...Jeffrey would like him to come at 8:30 ...I do not have any contact details for Steve...might you be able t

ch On Feb 19, 2013, at 3:41 PM, wrote: Not sure what time he lands and if he has wireless in flight.... From: Sent: 2/19/2013 11:49 AM To: Cc: Steven Sinofsky Subject: Re: Jeffrey Epstein tremendous...thanks for your help! Hi Steve! Make it 8:30pm tonight to Jeffrey's home please...he lives at: 9 East 7

EFTA00395424.pdf

EFTA00395424

2 mentions

e. He is copied on this email His mobile is Thank you. From: Sent: 2/19/2013 11:42 AM To: Subject: Jeffrey Epstein Hi ...I understand Steve (Sinofsky) will be coming to see Jeffrey tonight...Jeffrey would like him to come at 8:30 ...I do not have any contact details for Steve...might you be able t

From: MINEIM=Ia > To: Steven Sinofsky <1. > Subject: Re: Jeffrey Epstein Date: Tue, 19 Feb 2013 21:18:25 +0000 Thanks...I let Jeffrey know! On Feb 19, 2013, at 4:01 PM, Steven Sinofsk

EFTA00395303.pdf

EFTA00395303

2 mentions

ank you. From: Sent: 2/19/2013 11:42 AM To: Subject: Jeffrey Epstein the staff line...or you may call M, Jeffrey's I Ii ...I understand Steve (Sinofsky) will be coming to see Jeffrey tonight...Jeffrey would like him to coinc at S:30 ...I do not have any contact details for Steve...might you be able

From: Steven Sinofsky To: Subject: Re: Jeffrey Epstein Date: Wed, 20 Feb 2013 14:52:15 +0000 Thanks! Will do. He said he wanted to step out. We'll see. On Feb 20, 20

Sponsored

EFTA00395392.pdf

EFTA00395392

2 mentions

re. He is copied on this email His mobile is Thank you. From: Sent: 2/19/2013 11:42 AM To: Subject: Jeffrey Epstein Hi ..I understand Steve (Sinofsky) will be coming to see Jeffrey tonight...Jeffrey would like him to come at 8:30 ...I do not have any contact details for Steve...might you be able t

From: Steven Sinofsky < To: Subject: RE: Jeffrey Epstein Date: Tue, 19 Feb 2013 20:27:08 +0000 Importance: Normal thanks M...a couple of hours ago j said to come stra

EFTA00395399.pdf

EFTA00395399

2 mentions

ed on this email His mobile is Thank you. EFTA00395399 From: Sent: 2/19/2013 11:42 AM To: Subject: Jeffrey Epstein Hi ..l understand Steve (Sinofsky) will be coming to see Jeffrey tonight...Jeffrey would like him to come at 8:30 ...I do not have any contact details for Steve...might you be able t

From: MINEIM=la> To: Steven Sinofsky Subject: Re: Jeffrey Epstein Date: Tue, 19 Feb 2013 20:43:27 +0000 Hi Steve...l think Jeffrey did change the time since he spoke with you to 8:30.

EFTA00395415.pdf

EFTA00395415

2 mentions

e. He is copied on this email His mobile is Thank you. From: Sent: 2/19/2013 11:42 AM To: Subject: Jeffrey Epstein Hi ...l understand Steve (Sinofsky) will be coming to see Jeffrey tonight...Jeffrey would like him to come at 8:30 ...I do not have any contact details for Steve...might you be able t

From: Steven Sinofsky <E > To: IMMIMMIa > Subject: RE: Jeffrey Epstein Date: Tue, 19 Feb 2013 21:01:01 +0000 Importance: Normal I am on a plane now. Landing at 5. Can

Sponsored

EFTA00395138.pdf

EFTA00395138

2 mentions

is email His mobile is 206 724 1070 rote: Thank you. EFTA00395138 From: Sent: .42 AM To Subject: Jeffrey Epstein Hi ..I understand Steve (Sinofsky) will be coming to see Jeffrey tonight...Jeffrey would like him to come at 8:30 ...I do not have any contact details for Steve...might you be able t

From: Steven Sinofsky <[email protected]> To: Subject: Re: Jeffrey Epstein Date: Wed, 20 Feb 2013 15:14:58 +0000 No answer. Can we call? On Feb 20, 2013, at 10:07 A

EFTA00395157.pdf

EFTA00395157

2 mentions

ed on this email His mobile is 206 724 1070 Thank you. From: Sent: 2/19/2013 11:42 AM To: Subject: Jeffrey Epstein Hi a...I understand Steve (Sinofsky) will be coming to see Jeffrey tonight...Jeffrey would like him to come at 8:30 ..J do not have any contact details for Steve...might you be able to

From: To: Steven Sinofsky <[email protected]> Subject: Re: Jeffrey Epstein Date: Wed, 20 Feb 2013 15:50:21 +0000 (JE knows and has confirmed he will see you!!...) On Feb

EFTA00395382.pdf

EFTA00395382

2 mentions

From: To: Cc: Steven Sinofsky Subject: Re: Jeffrey Epstein Date: Tue, 19 Feb 2013 19:49:04 +0000 tremendous...thanks for your help! Hi Steve! Make it 8:30pm tonight to Jeffrey'

Sponsored

EFTA00395397.pdf

EFTA00395397

2 mentions

e. He is copied on this email His mobile is Thank you. From: Sent: 2/19/2013 11 42 AM To: Subject: Jeffrey Epstein Hi ...I understand Steve (Sinofsky) will be coming to see Jeffrey tonight...Jeffrey would like him to come at 8:30 ...I do not have any contact details for Steve...might you be able t

n Date: Tue, 19 Feb 2013 20:41:07 +0000 Not sure what time he lands and if he has wireless in flight.... From: Sent: 2/19/2013 11:49 AM To: Cc: Steven Sinofsky Subject: Re: Jeffrey Epstein tremendous...thanks for your help! Hi Steve! Make it 8:30pm tonight to Jeffrey's home please...he lives at: 9 East 7

EFTA00395405.pdf

EFTA00395405

2 mentions

From: Steven Sinofsky <E > To: IMMIMMIa > Subject: RE: Jeffrey Epstein Date: Tue, 19 Feb 2013 20:45:22 +0000 Importance: Normal got it. 8:30 it is. Call is at 7pm. Di

EFTA00395407.pdf

EFTA00395407

2 mentions

From: MINEIM=la > To: Steven Sinofsky Subject: Re: Jeffrey Epstein Date: Tue, 19 Feb 2013 20:54:02 +0000 terrific. thanks. 1 will pass along the details! On Feb 19, 2013, at 3:45 PM,

Sponsored

EFTA00395413.pdf

EFTA00395413

2 mentions

ch On Feb 19, 2013, at 3:41 PM. wrote: Not sure what time he lands and if he has wireless in flight.... From: Sent: 2/19/2013 11:49 AM To: Cc: Steven Sinofsky Subject: Re: Jeffrey Epstein tremendous...thanks for your help! Hi Steve! Make it 8:30pm tonight to Jeffrey's home please...he lives at: 9 East 7

staff line...or you may call M, Jeffrey's From: Sent: 2/19/2013 11:42 AM To: Subject: Jeffrey Epstein EFTA00395413 Hi ...I understand Steve (Sinofsky) will be coming to see Jeffrey tonight...Jeffrey would like him to come at 8:30 ...I do not have any contact details for Steve...might you be able t

EFTA00395410.pdf

EFTA00395410

2 mentions

From: To: Steven Sinofsky Subject: Re: Jeffrey Epstein Date: Tue, 19 Feb 2013 20:58:51 +0000 Steve, below is from Jeffrey...I think you are on the plane??!! "where are you

EFTA00395141.pdf

EFTA00395141

2 mentions

copied on this email His mobile is 206 724 1070 Thank you. From: Sent: 2/19/2013 11:42 AM To: Subject: Jeffrey Epstein Hi I understand Steve (Sinofsky) will be coming to see Jeffrey tonight...Jeffrey would like him to come at 8:30 ..J do not have any contact details for Steve...might you be able to

From: To: Steven Sinofsky <[email protected]> Subject: Re: Jeffrey Epstein Date: Wed, 20 Feb 2013 15:17:35 +0000 yes, please try again...i was away from my desk!! so sony

Sponsored

EFTA00395151.pdf

EFTA00395151

2 mentions

ere. He is copied on this email His mobile is Thank you. From: Sent: 2/19/2013 11:42 AM To: Subject: Jeffrey Epstein Hi .1 understand Steve (Sinofsky) will be coming to see Jeffrey tonight...Jeffrey would like him to come at 8:30 ..J do not have any contact details for Steve...might you be able to

From: Steven Sinofsky <[email protected]> To: Subject: Re: Jeffrey Epstein Date: Wed, 20 Feb 2013 15:36:53 +0000 Howdy thanks! JEE wants me to stop by. Best for me

EFTA00395153.pdf

EFTA00395153

2 mentions

his email His mobile is 206 724 1070 Thank you. wrote: From: Sent: 2/19/2013 11:42 AM To: Subject: Jeffrey Epstein Hill=.1 understand Steve (Sinofsky) will be coming to see Jeffrey tonight...Jeffrey would like him to come at 8:30 ...I do not have any contact details for Steve...might you be able t

From: To: Steven Sinofsky <[email protected]> Subject: Re: Jeffrey Epstein Date: Wed, 20 Feb 2013 15:44:16 +0000 You are welcome!! I'm sure Jeffrey will step out of his m

EFTA00395155.pdf

EFTA00395155

2 mentions

is copied on this email His mobile is 206 724 1070 Thank you. From: Sent: 2/19/2013 11:42 AM To Subject: Jeffrey Epstein Hi understand Steve (Sinofsky) will be coming to see Jeffrey tonight...Jeffrey would like him to come at 8:30 ..I do not have any contact details for Steve...might you be able to

From: Steven Sinofsky <[email protected]> To: Subject: Re: Jeffrey Epstein Date: Wed, 20 Feb 2013 15:46:09 +0000 Sounds good! On Feb 20, 2013, at 10:44 AM, ' wrote:

Sponsored

EFTA00395380.pdf

EFTA00395380

2 mentions

From: To: Subject: RE: Jeffrey Epstein Date: Tue, 19 Feb 2013 19:43:47 +0000 >, Steven Sinofsky Hi there. He is copied on this email His mobile is Thank you. From: Sent: 2/19/2013 11:42 AM To: Subject: Jeffrey Epstein Hi ..I understan

EFTA00700161.pdf

EFTA00700161

2 mentions

ubject: Re: Push on 20 do not fold On Tuesday, November 20, 2012, Steven Sinofsky wrote: Chatter over. Exhausting and more. WSJ doing "defense of Sinofsky" on their own. I can talk on Monday if I want before it runs. Price/lefkowitz talking. Fixated on specific companies I won't work for and non-solici

From: Steven Sinofsky To: Jeffrey Epstein <[email protected]> Subject: RE: Date: Wed, 21 Nov 2012 02:00:49 +0000 Not sure what leverage i have. I could get the s

Sponsored

Connected Entities(20 of 455)

Jeffrey Epstein