Michael Wolff — Investigation

Status: RESEARCH DRAFT — UNDER REVIEW

Who He Is

Michael Wolff (b. 1953) is a journalist and author best known for Fire and Fury: Inside the Trump White House (2018) and Siege: Trump Under Fire (2019). He met Jeffrey Epstein in the late 1990s during the internet bubble and maintained a continuous, documented relationship from at least 2011 through Epstein's death in August 2019. Wolff claims to possess approximately 100 hours of recorded interviews with Epstein across 30+ sessions.

The EFTA corpus contains 72 documents with Wolff's email addresses (highest confidence direct correspondence), plus 89 House Oversight emails and hundreds of scheduling, calendar, and phone records — totaling over 4,000 documents referencing Wolff across the corpus. The date range spans May 2011 through May 30, 2019 — six weeks before Epstein's final arrest. These documents reveal that Wolff operated not as a journalist covering Epstein, but as a strategic advisor, crisis manager, intelligence broker, social fixer, and counter-surveillance operative — while simultaneously writing profiles of his subject.

Email addresses: [email protected] (primary, 2012-2019), [email protected] (earlier, 2011-2013), [email protected] (Nov 2017, EFTA02571015), [email protected] (Dec 2017, EFTA02546930)
Phone: (917) 825-9659
Contact created in Epstein's device: 2012-02-01 (EFTA00597207)

Evidence Inventory

1. Crisis Management and PR Strategy

Wolff served as Epstein's de facto media strategist during at least three crisis periods, all occurring years after Epstein's 2008 sex offense conviction.

January 3, 2015: Virginia Roberts / Prince Andrew Allegations

When Virginia Roberts Giuffre's allegations naming Prince Andrew hit every British front page, Ian Osborne forwarded the coverage to Epstein. Wolff immediately engaged with detailed media strategy:

"I would not act till then. And I would hit very hard on media's willingness to hide behind court documents and repeat all manner of preposterous allegations. In that regard, I think you should prepare a detailed list of the most preposterous aspects of all this — this will give the NYT and WSJ some pause."

When Epstein mentioned Kathy Ruemmler (former White House Counsel) as a potential spokesperson, Wolff advised:

"I think that is a reasonably good approach. I might make the central point that court documents are a back door way to make protected libelous allegations. Plaintiffs in pursuit of settlements can wildly and improbably allege anything they want — the media then can repeat this without any obligation to verify."

The same email thread includes a reference to scheduling Bill Gates: "Can you give me time middle of the month and schedule Gates? Obviously, no time like now to deal with this."

Source: EFTA01791807-01791810 (DS10)

December 1-3, 2018: Miami Herald "Perversion of Justice" Response

Three days after the Miami Herald published its landmark investigative series, Wolff provided Epstein with a comprehensive crisis framework:

"At this point I don't think you can go legalistic. They've won the high ground — young, vulnerable, poor girls."

When Epstein asked "do you think we highlight, that at the end of the day it was prostitution. sex for money. a state crime. with state laws," Wolff replied:

"Don't tweet this."

Wolff then laid out a full strategic plan:

"What I'd like to do is game out everything, creating a structure for thinking this through. Definitely not a piecemeal response. Figure out where we want to be and where we can reasonably get and work backwards. Maybe we do agree to a big interview with you — Landon Thomas or something like that. But this has to be war gamed out. Obviously I can contribute, Kathy can, would be great to get SB input, but this needs a structure, that's why I think Holtzig or somebody assembling a plan would be helpful."

"SB" refers to Steve Bannon; "Kathy" to Kathy Ruemmler; "Holtzig" to Matthew Hiltzik, a public relations executive (Epstein's spelling).

Two days later, on December 3, Epstein's assistant organized an urgent conference call with four participants: Epstein, Wolff, Darren Indyke (personal attorney), and Kathy Ruemmler (Latham & Watkins attorney). Wolff negotiated the timing around his 12:30 lunch.

Source: EFTA02613104-02613107 (DS11), EFTA00486083 (DS9)

February 2016: Preemptive Trump/Hillary Strategy

Wolff warned Epstein that the New York Times had called him about Epstein's Trump connection, and that the Hillary Clinton campaign was "digging deeply":

"NYT called me about you and Trump. Also, Hillary campaign digging deeply. Again, you should consider preempting."

Epstein responded by inviting Wolff to meet Ehud Barak: "Im here today, ehud barak at 1, would you like to join at 2?"

Source: EFTA02368954-02368955 (DS11), HOUSE_OVERSIGHT_032238

December 15, 2015: CNN Debate Tip-Off

Wolff alerted Epstein hours before a CNN Republican debate:

"I hear CNN planning to ask Trump tonight about his relationship with you — either on air or in scrum afterwards."

He then advised Epstein on how to exploit the situation:

"I think you should let him hang himself. If he says he hasn't been on the plane or to the house, then that gives you a valuable PR and political currency."

Source: HOUSE_OVERSIGHT_032228, HOUSE_OVERSIGHT_032229 (DS99)

Ongoing: "The Trump Bullet"

By February 2016, Wolff had crystallized Epstein's strategic value in relation to Trump: "Yeah, you're the Trump bullet" (HOUSE_OVERSIGHT_032242). In January 2016, Wolff assessed media risks: "ABC doesn't really have an 'investigative unit' so unless you want to hand it to them they won't pursue" (HOUSE_OVERSIGHT_032231). In October 2016, Wolff urged Epstein to act: "Now could be the time — There's an opportunity to come forward this week and talk about Trump in such a way that could garner..." (HOUSE_OVERSIGHT_033179).

Source: HOUSE_OVERSIGHT_032231, 032242, 033179 (DS99)

2. Counter-Surveillance of Other Journalists

Wolff systematically monitored journalists investigating Epstein and reported back.

James Patterson / "Filthy Rich" (December 2015)

Wolff contacted Little, Brown's publicity department to investigate whether James Patterson was writing a book about Epstein. Publisher representative Sabrina Callahan responded that John Connolly had "been working on an investigation for several years" and he and Patterson "have met" but it was "too early to tell" whether there would be a book. Wolff forwarded this intelligence directly to Epstein.

When Epstein asked "who is nicole?" (referring to a forwarded contact), Wolff replied: "Somebody in publicity at Little, Brown."

Separately, Ellie Leonard has reported that Wolff later signed an NDA with Little, Brown to obtain an advance copy of the manuscript and allegedly forwarded the publisher email thread to Epstein.

Source: EFTA01806023-01806024 (DS10), Leonard reporting

John Connolly / Vanity Fair (November 2015)

When Epstein learned that Connolly was writing about him, Wolff advised on how to handle it:

"Connolly? Definitely not. But you should have one of the people he's calling for info ask him, if you can."

Wolff assessed whether Vanity Fair might publish an excerpt: "Is the question whether he's writing it for VF? The answer would be no. Might they publish an excerpt from such a book were it to be written? Possibly." When Epstein asked Wolff to check with Graydon Carter (VF editor), Wolff responded with this analysis.

The email chain includes a forwarded message from Connolly to a source: "I am a writer for Vanity Fair magazine and I am writing a book on Jeffrey Epstein."

Source: EFTA02347714-02347715 (DS11)

3. The Killed New York Magazine Profile (2014-2015)

From September 2014 through March 2015, Wolff worked on a 7,000-8,000 word profile of Epstein for New York Magazine. The correspondence reveals Epstein exercised extraordinary editorial control:

Fact-checking through the subject: Wolff sent Epstein passages for approval, including investment claims ("If I had invested $100,000 the way Epstein said I should in early September, by the end of January I would have made $2.3 million. Alas, I did not.") and legal characterizations about prosecutor Lana Belhalevic: "Do you have anything I can quote from here — was there an official finding?" (EFTA01746747, EFTA01747374)

"Names in order": Wolff urgently requested "that section with names in order ASAP" — suggesting Epstein was providing a curated list of people to include (EFTA01746756).

Photo control: When NY Mag wanted a photo shoot in Epstein's dining room, Epstein initially refused. Wolff pushed: "It won't [suffice to use existing photos]. Very much not. Can you do it on Saturday morning in NYC? I will come with them. Can be done in 30 minutes." Epstein later bought the photos for $15,000 "as I did not trust him" and insisted the magazine "should need approval and you should see them first" (EFTA01747050, EFTA01746720).

Magazine loved it: On February 6, 2015, Wolff reported: "they have seen the piece and love it — they wonder only if we ought to cut back on the sex/scandal stuff and not let it overwhelm the larger story" (EFTA02342548).

Gates comment sought: In late March, Wolff told Epstein: "need Gates comment, if possible." Epstein responded "number?" (EFTA02354006).

Epstein kills it: On March 31, 2015, Epstein pulled the plug: "sorry, but this will create many more problems than either you [or] i want to deal with. cannnot. must rethink, will call in 1 hr." (EFTA02506207)

After the article was killed, Wolff pivoted to an identity-branding discussion. Epstein dictated how he wanted to be perceived: "the focus on me having all the answers, is less good than me having better questions to ask of people. getting them to think in a different way. people leaving saying wow that was a good question" (EFTA02403629).

Ben Smith at Semafor later reported that Wolff had shared an 8,684-word unpublished draft directly with Epstein that portrayed abuse victims as "prostitutes who lied about their age."

4. Social Brokering and Intelligence Pipeline

Wolff served as a conduit between Epstein and political, media, and intellectual figures.

Steve Bannon

Wolff arranged a meeting between Bannon and Epstein in October 2017, forwarding Bannon's messages directly:

"JE leaves for Paris tomorrow at 9:30AM. Could meet before or tonight."

Bannon responded: "Can't make tomorrow. Can we resked for when he returns." Bannon had been "in CT w/ donors to my revolution."

Source: EFTA02589079 (DS11)

In January 2017, Wolff told Epstein about "the six-hour dinner I had with Ailes and Bannon last week at my house" and relayed that Ailes "would like to organize something with you" (EFTA02664993).

Throughout 2017, Wolff reported to Epstein after meetings with Bannon at the White House: "Just did two hours with Bannon on who's trying to kill whom" (EFTA02396924); "Four hours with Bannon. He ripped the sheets off" (EFTA02642870).

In Bannon-Epstein iMessages, Epstein read Wolff's Siege and gave Bannon a detailed briefing: "I have now seen some of Wolffs book. Mentions me and underage prostitutes. You as the man behind and in front of the curtain. Lots of Steve quotes." When Wolff publicly claimed Bannon had "knowledge of Trump's crimes," Bannon asked Epstein: "Tell him to lay off me." Epstein replied: "Ok." Then: "done." (EFTA01615894, EFTA01615911)

Roger Ailes

In November 2016, Wolff facilitated contact between Epstein and Roger Ailes, who was "paranoid" and "wary of being seen":

"He is not so much shy, as paranoid. I have to contact him through his wife on a burner phone, which they don't reliably check. But have queried."

Epstein proposed: "would you like to ask him to dinner tomorrow night you me and woody my house." Wolff replied: "My guess is that he will be too paranoid. He believes NYP photographers are following him. But will ask."

In the same exchange, Epstein told Wolff: "Ive set you up to see the right hand of the Dep Cr Prince" — referring to Saudi Arabia's Deputy Crown Prince (Mohammed bin Salman).

Source: EFTA01787496-01787532 (DS10)

Noam Chomsky / James Watson

In June 2018, Epstein told Wolff: "chomsky ready when you are? tucson. we should do watson. harvard, asap." Wolff confirmed: "He's in Tucson?" Epstein was brokering introductions for Wolff with Noam Chomsky and Nobel laureate James Watson.

Source: EFTA02518925 (DS11)

Governor Bill Richardson

On March 19, 2013, Wolff attended a private three-person lunch at Epstein's Manhattan residence with Governor Bill Richardson.

Source: EFTA02144735 (DS10)

Epstein Prepping Wolff for Trump Interview (May 2016)

Epstein coached Wolff on specific questions for an interview with Donald Trump:

"maybe you can ask why bernie nussbaum got vince fosters letter quickly, that is a hillary problem. he would smile then you can ask his relationships with the electricians unions and maralago. and out you go"

Wolff responded: "Job is to get the hard ones in without being ejected from the room. What's the one question that pierces through?"

Epstein offered: "do you want to be provocative? trump shuttle. hawaiian tropic contests. mortgage on mara lago? revenue of golf courses as income.??! total debt of all cos?"

Source: HOUSE_OVERSIGHT_029272 (DS99)

5. The "Assistant" Referrals

Two separate instances of Wolff offering to connect young women with Epstein as "assistants" are documented.

November 8-9, 2013

Subject line: "Re: Assistant"

Wolff: "If you're still looking for an assistant...girl I know, 24-25ish, graduate student at Columbia very bright and adventurous, could be what you're looking for, named [REDACTED]"

Epstein: "Great, next step? Skype her"

Wolff: "Want me to put her directly in touch?"

The name is redacted with asterisks. This exchange occurred five years after Epstein's 2008 sex offense conviction and public registration as a sex offender.

Source: EFTA01755627 (DS10)

November 11, 2013 (Two Days Later)

A separate email shows Wolff formally introducing someone to Epstein:

"[Name] — I know Victoria mentioned to you that my good friend Jeffrey Epstein is looking for an assistant. So let me introduce the two of you. Jeffrey, [name]. Jeffrey. Best, m"

This introduction was CC'd to Epstein and references Victoria Floethe having already spoken to the candidate.

Source: EFTA02345617 (DS11)

6. Opposition Research for Epstein

Lady Lynn Rothschild (December 2012)

After a lunch, Wolff casually asked Epstein for intelligence on DOJ matters: "And if you do happen to hear anything out of DOJ re FCPA or RICO, I'd love to know." Epstein deflected and tasked Wolff with opposition research: "reserach lady rothschild lynn forester, foremerly lynn stein, andrew stein."

Wolff replied: "on the job..."

Source: EFTA01914363 (DS10)

Panama Papers (April 2016)

When the Panama Papers leaked, Wolff asked Epstein: "In addition to all else, need any insights into this Panama Papers leak." Epstein replied: "I'm your man."

Source: EFTA02466944 (DS11)

7. Fire and Fury: Epstein as Source and Facilitator (2017-2018)

On February 15, 2017, Wolff told Epstein about his Trump book project:

"A few favors... So...I'm doing this Trump book for a pile of money and with so far quite a bit of cooperation from them (DT...)"

In the same message, Wolff asked Epstein for an introduction to Tom Barrack: "Dear Jeffrey, You mentioned you were friends with Tom Barrack and I wondered if you might introduce me to him" (HOUSE_OVERSIGHT_032474).

After Fire and Fury was published in January 2018, Wolff assured Epstein the book contained only minimal reference to him: "Just passing reference that you, Tom Barrack, and Trump were once friends. One mention. No inference" (HOUSE_OVERSIGHT_032708). Epstein ordered six signed copies through Groff (EFTA01014152).

On January 5, 2018, Epstein and Wolff discussed Bannon's role: "you and I will script in detail, and document if you think important" (EFTA02542648).

In February 2019, Wolff sent Epstein draft text from his upcoming book for review: "Books and newspaper accounts of Trump's 45 years in business were full of his shady dealings, and the presidency had only..." (HOUSE_OVERSIGHT_030987).

Source: HOUSE_OVERSIGHT_032471, 032474, 032708, 030987 (DS99), EFTA02542648 (DS11)

8. Ken Starr Introduction

Wolff personally introduced Epstein to Ken Starr, writing to Starr: "Jeffrey has long told me about your friendship and the respect he has for you" (HOUSE_OVERSIGHT_033564, May 19, 2018). This introduction preceded the December 2018 crisis, when Starr drafted a public statement defending the Acosta plea deal that was forwarded to Wolff, Ruemmler, Indyke, and Hiltzik.

Source: HOUSE_OVERSIGHT_033564, HOUSE_OVERSIGHT_030318 (DS99)

9. The "JE Documentary" (May 2018)

In May 2018, Wolff and Epstein were planning a documentary about Epstein ("JE doc"). Wolff suggested: "Ken would be good for JE doc too." The two compiled a guest list:

Epstein's list: Woody Allen, Noam Chomsky, Ehud Barak, James Watson, Ariane de Rothschild, Masha Drokova, Ruemmler, Leon Black, Tom Pritzker, Larry Summers, Joi Ito, Terje Roed-Larsen, Deepak Chopra, Jacques Lang, Martin Nowak, Mark Tramo.

Wolff's additions: "All v good. More women. An Arab. Bannon. Brad Karp." Epstein added: "bill gates. nathan myhrvold. ?"

This was May 2018 — 14 months before Epstein's final arrest.

Source: EFTA02660733-02660734 (DS11)

8. Woody Allen Strategy (2017-2018)

Wolff served as a strategic advisor on Woody Allen's public relations during the #MeToo era, reporting back to Epstein.

After dinner with Allen and Soon-Yi Previn, Wolff reported: "They both seemed to understand the importance and power of SY speaking out. And they were both filled with devastating stories about Mia (did you know that when she was with Frank she had an affair with Polanski?). But today Woody seemed to have cold feet and said he didn't want to take down Mia" (EFTA02528943).

Wolff advised Epstein on Allen's strategy: "He has to turn this into a love story with Soon-Yi. She's the only one who can save him." Epstein replied that Allen's "brain trust" was "all old thinkers. no social media strategy" (EFTA02537150).

In October 2017, Wolff reported that "Victoria saw Soon Yi yesterday and they seem worried and, it appears, more open to ideas" (EFTA02356445).

9. Frequency and Nature of Contact

Wolff was a regular visitor to Epstein's Manhattan residence at 9 East 71st Street for breakfasts and lunches, often scheduled by Lesley Groff. Documented visits and contact span every year from 2011 through 2019:

Sample calendar entries showing same-day companions:
- May 1, 2011: Wolff (1pm), alongside Leon Black (10:30am), Howard Lutnick (5pm drinks), dinner with Woody Allen and Soon-Yi (Glenn Dubin may attend) (EFTA00307005)
- Feb 16, 2012: Wolff breakfast (9am), dinner with Woody Allen, Soon-Yi, Dick Cavett (7pm) (EFTA02033120)
- Apr 8, 2014: Wolff breakfast (9am), Leon Black lunch (12pm) (EFTA01928446)
- Jan 15, 2018: Epstein's party fantasy — "woody barrack. bannon. ruemmler." (EFTA02538406)

Epstein gifted Wolff sneakers he had "admired" during a visit (EFTA02188806). Wolff and Victoria Floethe traveled to Paris to dine at Epstein's apartment at 22 Avenue Foch on multiple occasions (August 2011, June 2013, November 2013). After one Paris dinner, Wolff wrote: "Well that was great fun. I loved that guy. And Victoria loved you" (EFTA01854608).

10. Reputation Management Website (2011-2012)

Starting in mid-2011, Wolff and Ian Osborne (British media consultant) collaborated on a website/reputation management project for Epstein. Wolff described it as requiring "strategy, goals, and story" before moving to "design and structure"; Osborne added a focus on Google search results (EFTA01987731).

By January 2012, Osborne sent an "updated plan with timeline" and noted they were "not obliged to put the finished site up" — the agreement was being sent to Darren Indyke. Epstein insisted: "Please do nothing on my project until we have a serious conversation in person" (EFTA01842794).

11. #MeToo Intelligence (December 2017)

Wolff provided Epstein with predictions about which public figures would face #MeToo allegations:

"And they won't be the last. My buddy, Lorin Stein, who runs the Paris Review — the Paris Review for god's sake! — just went down. The 80-year-old father of my friend Rachel Horovitz — the playwright Israel Horovitz — whacked. Big names on the horizon: Michael Douglas, Larry Gagosian, and still my favorite, Arthur Sulzberger."

He shared concerns about Woody Allen specifically: "I have a bad feeling about this new Woody round. It could pull him into the general Harvey pool of the despised and shunned." He added: "I think Bannon may be right. This is not going to end until Trump goes down."

Source: EFTA02549109-02549110 (DS11)

12. Ken Starr PR Strategy Chain (December 2018)

In the wake of the Miami Herald series, Ken Starr drafted a public statement defending the Acosta plea deal and sent it to Epstein (CC: Dershowitz). The chain was forwarded to Wolff, CC'ing Ruemmler, Indyke, and Hiltzik. Wolff asked:

"Is there reason or opportunity here to evoke JE's Clinton connection?"

Source: HOUSE_OVERSIGHT_030255, HOUSE_OVERSIGHT_030315, HOUSE_OVERSIGHT_030318 (DS99)

Key External Reporting

Ellie Leonard (Blue Amp Media / Substack) has published the most detailed investigations:

• "100 Hours With Epstein: Epstein's Double Agent" (Blue Amp Media)
• "Michael Wolff Has Entered the Chat" (Substack)

Key emails from the House Oversight Committee release (November 2025), widely reported by CBS News, Al Jazeera, Fortune, and others:
- December 15, 2015: Wolff tipped Epstein that CNN was planning to ask Trump about his Epstein relationship during a debate, advising: "I think you should let him hang himself. If he says he hasn't been on the plane or to the house, then that gives you a valuable PR and political currency"
- March 2016: Wolff proposed a comprehensive counter-narrative strategy to Epstein ahead of Filthy Rich publication, arguing that Trump offered "an ideal opportunity" and "becoming an anti-Trump voice gives you certain political cover"
- January 31, 2019: Epstein wrote to Wolff: "Trump said he asked me to resign, never a member ever. Of course he knew about the girls as he asked Ghislaine to stop"

Ben Smith at Semafor reported that Wolff shared an 8,684-word unpublished draft directly with Epstein that portrayed abuse victims as "prostitutes who lied about their age."

Additional coverage: Tara Palmeri / The Red Letter, Washington Monthly (Jonathan Alter interview with Wolff about recordings).

Summary Assessment

The documentary record reveals Michael Wolff as one of the most deeply embedded figures in Epstein's post-conviction network. Unlike other journalists who covered Epstein, Wolff simultaneously:

1. Provided crisis communications strategy during at least three major threat periods (2015, 2016, 2018)
2. Monitored and reported on other journalists investigating Epstein (Patterson, Connolly, BBC)
3. Gave his subject editorial control over a major magazine profile, then accepted its cancellation
4. Served as social broker between Epstein and political figures (Bannon, Ailes, Saudi Deputy Crown Prince)
5. Conducted opposition research on Epstein's targets (Rothschild, Trump financial disclosure)
6. Referred young women as "assistants" to a registered sex offender (two documented instances, November 2013)
7. Participated in legal crisis calls alongside Epstein's attorneys (Indyke, Ruemmler)
8. Helped plan a rehabilitation documentary featuring world leaders and Nobel laureates
9. Shared #MeToo intelligence predicting which figures would face allegations
10. Received reciprocal access: Epstein facilitated introductions to Chomsky, Watson, Richardson, Saudi royals, and White House intelligence

The question raised by Ellie Leonard — why Wolff won't release his 100 hours of Epstein recordings — should be understood in the context of this documentary record. The tapes would reveal not just what Epstein said, but the full nature of a relationship in which a journalist functioned as a consigliere.

Complete EFTA Index

Direct Correspondence (verified, read in full)

Bannon-Epstein iMessages (Wolff discussed)

House Oversight Documents (DS99)

iMessage Threads

Additional DS11 Confirmed Correspondence

Calendars / Scheduling

Social Events

Complete Communication Index

The above tables document the ~100 highest-value documents read in full. The complete corpus sweep identified 4,042 unique documents referencing Michael Wolff across all datasets:

Dataset distribution (Tiers 1+2: 1,896 direct correspondence docs):

Data files:
- WOLFF_MASTER_LIST.csv — 1,897 rows, Tiers 1+2 combined. Columns: efta_number, dataset, total_pages, match_type