As Jeffrey Epstein was reeling from a 2018 Miami Herald investigation about the sweetheart deal he struck with federal prosecutors to settle claims he had sexually abused teenage girls, the financier turned to a trusted confidant for advice: journalist Michael Wolff.

In a series of messages found in the trove of more than 20,000 documents released Wednesday by the House Oversight Committee investigating Epstein’s crimes, the independent journalist and author suggested that any potential response needed to be “war gamed out” and initially proposed that they find a sympathetic reporter to interview Epstein.

Wolff rejected Epstein’s proposals to attack the reporting or publicly claim that the alleged sexual abuse was really “prostitution,” saying that Epstein had lost the “high ground.”

Eventually Wolff and Epstein reached a consensus.

“(I)m thinking what would trump do,” Epstein wrote.

Wolff, author of several best-selling books about President Donald Trump, replied, “He never tries to explain. He denies, blames media, denigrates someone else.”

The exchange occurred on Dec. 1, 2018, three days after the Herald published its “Perversion of Justice” investigation which showed how Epstein, the now-deceased financier, and his high-priced attorneys had been able to bend the justice system in South Florida to their will, cutting out dozens of his victims in the process.

The emails are part of a broader investigation by the House Oversight Committee into Epstein’s sex crimes as questions have swirled about what President Trump knew of them. Epstein’s estate provided the committee with thousands of documents, several of which Democrats released early Wednesday before Republicans unleashed the 20,000.

Epstein died in federal custody in August 2019, a month after federal prosecutors in the Southern District of New York brought new sex charges against him following the Herald’s reporting.

’Juicy info’

While Epstein’s friendships with billionaires, politicians and royalty have been well-documented, the newly released documents reveal the close relationship he appeared to enjoy with two journalists: Wolff and former New York Times reporter Landon Thomas Jr.

Epstein’s relationship with Trump takes center stage in hundreds of pages of correspondence with Wolff and Thomas released by the committee.

Writing about Trump in January 2019, Epstein told Wolff, “of course he knew about the girls.”

In December 2015, Epstein asks Thomas if he would like photos of “donald and girls in bikinis in my kitchen.”

The messages between the serial sex abuser and the two reporters provide insight into how Epstein was able to maintain relationships with some of the most powerful people in the world, even after he had been convicted of sex crimes.

In the messages, Epstein is a consummate gossip and matchmaker, trading tidbits on politics and finance with the reporters, and opening up his now infamous Rolodex to connect the two reporters with sources.

In exchange, they provided him advice and gave him warnings about reporting that could mention him, particularly in regard to his relationship with Trump.

When Wolff counseled Epstein in December 2018 following the Herald’s investigation, the author specifically suggested that Epstein agree to an interview with Thomas.

The two had a history.

Thomas was the author of a 2002 New York Magazine article about Epstein titled “Jeffrey Epstein: International Moneyman of Mystery.”

The dishy profile, highlighting Epstein’s jet-setting lifestyle while raising questions about just how he earned his fortune, is perhaps best remembered now for a character reference provided by Trump.

“I’ve known Jeff for fifteen years. Terrific guy,” Trump told Thomas over speakerphone. “He’s a lot of fun to be with. It is even said that he likes beautiful women as much as I do, and many of them are on the younger side.”

But Thomas and Epstein’s relationship didn’t end with that piece.

Thomas wrote another story about Epstein in 2008, this time for the New York Times, as Epstein reported to the Palm Beach County jail where he would serve 13 months as part of his plea deal with prosecutors. Epstein was given extraordinary privileges during his period of incarceration, housed in a private wing and allowed to leave each day to work at a Palm Beach Office, where he continued to have sex with teenage girls.

As Thomas wrote, he interviewed Epstein on his “palm-fringed Xanadu” at Little St. James Island in the British Virgin Islands – where Epstein is accused of sexually assaulting dozens of girls – and quoted Epstein describing his crimes as “playfulness,” and explaining away his legal troubles as a consequence of his wealth.

Thomas was in touch with Epstein in December 2015 as the financier’s relationship with Trump became a talking point during the 2016 presidential campaign, writing in one of the leaked messages “everyone coming to me thinking I have juicy info on you and Trump.”

That’s when Epstein offered Thomas photos of Trump with girls in bikinis in Epstein’s kitchen, though it’s not clear whether he ever sent Thomas the photos or if the photos existed.

Epstein’s reply referenced a woman named Lauren Petrella who had accused Trump of unwanted sexual advances during a beauty pageant.

Thomas asked Epstein if he could share Petrella’s contact information with his colleague, with the caveat “I won’t do it unless you say OK because after that I would have no say as to where story goes.”

Epstein demurred and Thomas appeared to have dropped his request, ending the exchange, “Maybe I will wait for the pics in your kitchen:)”

Leveraging Epstein’s influence

The exchanges between Epstein and the reporters show how they turned to the financier for inside information and introductions.

“[W]ho is treasury secretary? Is Mnuchin a done deal? Seems too obvious,” Thomas writes to Epstein two days after the 2016 election.

Wolff, meanwhile, wrote to Epstein in 2017 for introductions to Trump friend and fundraiser Tom Barrack, who is currently the ambassador to Turkey, as well as Kathy Ruemmler, a former White House attorney in the Obama administration Epstein communicated with regularly, according to the released emails. Ruemmler is now the chief legal counsel at Goldman Sachs.

The interviews would inform Wolff’s 2018 bestselling book ‘Fire and Fury,’ which he told Epstein he wrote “for a pile of money.”

At work on his follow-up, Wolff asked Epstein for an introduction to Epstein’s former attorney Ken Starr, who had previously been the independent counsel whose investigation led to the 1998 impeachment of Bill Clinton.

In an exchange, Wolff and Thomas gave Epstein a heads up when they heard about reporting that would mention him and offered Epstein advice on how to respond.

Thomas wrote to Epstein in June 2016 that he kept getting calls from John Connolly, who co-wrote with James Patterson the 2016 book “Filthy Rich” about Epstein.

“I told him you were a hell of a guy:),” Thomas wrote.

But the messages didn’t stop with just notifications of upcoming coverage.

Wolff also offered Epstein advice about how to handle negative attention in the press, particularly as it related to his relationship with Trump.

Wolff wrote to Epstein on Dec. 15, 2015, that he had heard that Trump might be asked about his relationship with Epstein during a Republican presidential debate that day on CNN.

After telling Epstein about the potential question in the CNN debate, for example, Wolff advised Epstein that if Trump tried to downplay their relationship, Epstein could use that information to his advantage.

“I think you should let him hang himself,” Wolff wrote. “If he says he hasn’t been on the plane or to the house, then that gives you a valuable PR and political currency. You can hang him in a way that potentially generates a positive benefit for you, or, if it really looks like he could win, you could save him, generating a debt.”

‘Wildly inappropriate’

The exchanges between Epstein and both Wolff and Thomas are troubling, said Margaret Sullivan, a columnist for the Guardian who teaches a course on journalism ethics at the Columbia Journalism School.

“I wouldn’t want to see myself associated with those emails as a journalist,” Sullivan said.

Wolff, as an independent journalist, “has a reputation for doing things that are not by the book” she said.

“But this is in a whole other category,” she said. “It’s wildly inappropriate.”

She said it was also problematic that Thomas appeared to drop his 2015 inquiry into what Epstein knew about Trump’s dealings with women.

“It should have been pursued very aggressively and we really don’t know what happened,” she said.

Wolff’s relationship with Epstein appeared to be largely beneficial to his career. Epstein helped provide sources for his wildly successful 2018 book “Fire and Fury” and subsequent follow-ups.

An attorney who represents Wolff didn’t respond to multiple requests for comment from the Herald.

Thomas’s relationship with Epstein didn’t end as well.

In 2019, Thomas was fired from the Times after revealing that he had solicited a $30,000 donation from Epstein for a preschool in Harlem.

An e-mail address associated with a substack newsletter Thomas created bounced.

A New York Times spokesperson said that Thomas was let go “after editors discovered his failure to abide by our ethical standards.”

He hasn’t worked in another newsroom since.

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