Jeffrey Epstein, once a powerful figure among the elite, found himself ostracized following his conviction for soliciting sex from a teenage girl and his failure to rehabilitate his tarnished image as a sexual predator. In 2011, an embittered Epstein turned his thoughts to an old acquaintance, Donald Trump, who, he believed, had managed to evade similar scrutiny.

In a letter to his longtime confidante Ghislaine Maxwell, Epstein expressed surprise that Trump, whom he referred to as “the dog that hasn’t barked,” had not been implicated in any scandal. Epstein noted that Trump had “spent hours at my house” alongside Virginia Giuffre, a woman who had publicly accused Epstein of abuse. This correspondence, among more than 20,000 documents obtained from Epstein’s estate, was released this week by the House Oversight Committee, shedding light on the complex relationship between Epstein and Trump.

At the time of the message, Epstein was at one of the lowest points in his life. He had recently completed a jail sentence in Florida for soliciting a minor and faced additional legal setbacks. Just two months prior, a judge in Manhattan had denied his request to lower his sex offender status, despite having influential support from figures like then-District Attorney Cyrus Vance, Jr.

Virginia Giuffre had become one of the most vocal accusers, alleging that Epstein had trafficked her to powerful men. Her claims gained traction when she provided the Daily Mail with a notorious photograph featuring herself, Prince Andrew, and Maxwell, underscoring her allegations.

In his 2011 communication with Maxwell, Epstein remarked on Trump’s ability to remain unscathed by controversy, even as Trump was gaining prominence as the host of “The Apprentice” and contemplating a presidential run. Epstein’s surprise at Trump’s absence from scandal underscores the intricate dynamics and secrets within their social circle.

Epstein’s 2011 email to Maxwell marveled that Trump, then hosting “The Apprentice” and floating a run for president had “never once been mentioned.”

“I have been thinking about that…,” Maxwell replied.

Democrats released Epstein’s 2011 message to Maxwell among a set of emails early Wednesday that appeared to suggest the president knew about the financier’s depraved lifestyle and its young victims.

Claiming that their colleagues across the aisle had engaged in a cherry-picking mission, House Republicans later published thousands of Epstein’s digital files online, revealing Giuffre’s identity in the 2011 message, which the Democrats had previously redacted. Many came to the president’s defense, arguing that it proved nothing. Giuffre, they noted, had denied that Trump had abused her or that she’d seen him abuse others in the years before her death.

The president has long denied engaging in any abuse and claimed he stopped talking to Epstein — whom he’d counted as a friend since the 1980s — in the early 2000s over a dispute related to real estate.

On Friday, following a barrage of reporting about the emails, Trump took to his social media site Truth Social to slam what he calls the “EPSTEIN HOAX.” He demanded the Justice Department investigate Epstein’s “involvement and relationship with Bill Clinton, Larry Summers, Reid Hoffman, J.P. Morgan, Chase, and many other people and institutions, to determine what was going on with them, and him.”

Attorney General Pam Bondi said Jay Clayton, U.S. Attorney for the Southern District of New York, would head the probe.

Dirt on Trump

The trove of Epstein emails released this week, massive in volume and spanning 2011 to 2019, includes 1,625 references to Trump, although there is no direct communication between the two men.

Made clear throughout is that — whether or not he did — Epstein maintained he had dirt on Trump.

Messaging ahead of a presidential debate in December 2015, Epstein asked his quasi-consultant, Trump biographer Michael Wolff, with whom he spoke regularly, how Trump might best answer a potential question about their relationship.

“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. 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,” Wolff responded.

“Of course, it is possible that, when asked, he’ll say Jeffrey is a great guy and has gotten a raw deal and is a victim of political correctness, which is to be outlawed in a Trump regime.”

Wolff suggested it could be time to pull the trigger less than two weeks before Trump won the presidency in 2016, following the release of “Filthy Rich,” a book about Epstein’s perversions.

“There’s an opportunity to come forward this week and talk about Trump in such a way that could garner you great sympathy and help finish him. Interested?” Wolff wrote on Oct. 29. It’s not clear from the release whether Epstein responded.

The batch of emails released this week, made searchable online by the Courier Newsroom, is separate from the federal government’s investigative records — the so-called “Epstein files” — whose release the House of Representatives is set to vote on next week.

The trove sheds light on Epstein’s state of mind in the years before his death, and how closely he followed the president’s whereabouts, policy moves, and his own set of scandals. In countless typo-laden emails, the Brooklyn-born financier situated himself as a POTUS expert in conversations with journalists and various confidants, spoke with members of Trump’s inner circle, and sought to shape U.S. policy.

In June 2018, he asked former Norwegian Prime Minister Thorbjørn Jagland to convey a message to Russian President Vladimir Putin about his willingness to provide insight on Trump.

His correspondence with Wolff is featured throughout the records, and Epstein also frequently spoke about Trump with former New York Times reporter Landon Thomas Jr., joking about sending him a photo of Trump with girls in bikinis in his kitchen in December 2015.

Epstein communicated regularly with the often foul-mouthed former Treasury Secretary Larry Summers, whom he told Trump was “borderline insane,” the emails show.

He also chatted often with Trump adviser Steve Bannon, who in August 2018 told the financier they had to discuss “a crazed jihad against u,” and that “somebody big has u in the gunsights.”

After Trump’s personal lawyer, Michael Cohen, pleaded guilty to breaking campaign finance laws for then-President Trump in the now-notorious Stormy Daniels hush money scheme in 2018, Epstein alluded to his insider’s perspective in correspondence with Kathy Ruemmler, a former Goldman Sachs executive and Obama aide, with whom the cache shows he frequently chatted.

“You see, i know how dirty donald is,” the financier quipped. “my guess is that non-lawyers ny biz people have no idea. what it means to have your fixer flip.”

“The real villain”

That December, The Miami Herald published the most complete account yet of allegations Epstein had serially exploited vulnerable teenage girls. The piece laid out how Epstein had effectively gotten off with a slap on the wrist in his 2008 plea deal due to former U.S. Attorney Alexander Acosta, who Trump had tapped as his Labor Secretary.

Epstein strategized with Wolff, who believed “directly debunking” the claims wasn’t the right move.

“That’s going against virtue itself,” Wolff wrote. “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.”

Epstein replied, “im thinking what would trump do.”

“Claims are ludicrous and self-serving, media is working with the other side’s lawyers, this is all about Donald Trump,” Wolff responded.

“…all about Donald Trump, the real villain,” Epstein said.

Less than two months later, Epstein explicitly implicated Trump, mentioning Mar-a-Lago to Wolff in a partially redacted email on January 31, 2019, and writing, “trump said he asked me to resign, never a member ever. . of course he knew about the girls as he asked ghislaine to stop.”

Epstein was apparently still focused on the president the following June, when an email outlining some of Trump’s potentially questionable financial dealings landed in his inbox. Epstein’s accountant Richard Kahn sent over “interesting findings” from financial disclosures, or what Kahn called “trumps 100 pages of nonsense.”

Within eight weeks, Epstein was dead. Officials said he’d killed himself in his lower Manhattan jail cell a month after his arrest on sweeping sex trafficking charges.

Maxwell, his longtime partner in crime, was indicted a year later for aiding the abuse for at least a decade in the 1990s and convicted at trial in December 2021. This summer, she was transferred to a cushy prison facility in Bryan, Texas, after meeting with Deputy Attorney General Todd Blanche, Trump’s former personal lawyer, for a highly unusual sit-down.

Transcripts of the meeting showed that Epstein’s longtime right-hand revealed little new information but notably praised the president, whom she is reportedly now planning to ask for a pardon.