After Trump Split, Epstein Said He Could ‘Take Him Down’

President Trump’s long friendship with Jeffrey Epstein came to an apparent end in the mid-2000s. But Mr. Epstein remained intently focused on Mr. Trump for years afterward, seeking to exploit the remnants of their relationship up until his arrest on federal sex-trafficking charges in 2019.

In more than 20,000 pages of Mr. Epstein’s typo-strewn emails and other messages released by a congressional committee on Wednesday, Mr. Epstein insulted Mr. Trump and hinted that he had damaging information on him.

By turns gossipy, scathing and scheming, the messages show influential people pressing Mr. Epstein for insight into Mr. Trump, and Mr. Epstein casting himself as the ultimate Trump translator, someone who knew him intimately and was “the one able to take him down.”

The release of the messages instantly pushed the two men’s much-scrutinized relationship back into the public eye, re-energizing Democratic attacks on Mr. Trump and his Justice Department for failing to publicly disclose more information from the investigation of Mr. Epstein.

The emails date to at least 2011, when Mr. Trump was a reality TV star toying with a long-shot presidential run and Mr. Epstein was trying to rehabilitate his image after his conviction and incarceration for soliciting prostitution from a minor. The messages continue through the spring of 2019, when Mr. Trump was president and his Justice Department was building a criminal case against Mr. Epstein.

The messages hint that Mr. Epstein or his advisers believed they had inside — and potentially damaging — knowledge of Mr. Trump’s far-flung properties and business dealings. Some suggest that Mr. Epstein thought Mr. Trump knew more about his personal conduct than the president has publicly acknowledged.

The trove doesn’t appear to include messages from Mr. Trump or anyone purporting to speak on his behalf. The president responded on social media on Wednesday, writing that “the Democrats are using the Jeffrey Epstein Hoax to try and deflect from their massive failures, in particular, their most recent one — THE SHUTDOWN!”

The emails, the latest batch of Epstein-related documents, were obtained from the Epstein estate in response to a subpoena from a congressional committee. They offer a clear window into his day-to-day communications with friends and associates.

But they are unlikely to quell the furor around the Trump-Epstein relationship. A core part of Mr. Trump’s base believes the mother lode of documents, audio files and video related to Mr. Epstein are in the possession of the Federal Bureau of Investigation and Justice Department. A slice of those documents has been released only in small, curated batches.

The basic contours of their relationship have long been known. Mr. Trump and Mr. Epstein were friends in the 1980s and 1990s, attending social events in New York or Florida together. One of Mr. Epstein’s former girlfriends has accused Mr. Trump of groping her, an allegation that Mr. Trump has denied. Mr. Trump has said that he cut ties with Mr. Epstein after his associates recruited teenage girls from Mr. Trump’s Mar-a-Lago estate.

But the new emails show that Mr. Epstein was closely following Mr. Trump’s business decisions and political fortunes.

In April 2011, Mr. Epstein wrote to his longtime associate Ghislaine Maxwell, who was later convicted of helping orchestrate Mr. Epstein’s sex-trafficking operation, that Mr. Trump was the “dog that hasn’t barked.” One of Mr. Epstein’s victims, Virginia Roberts Giuffre, had recently gone public about her experiences with Mr. Epstein — telling a British tabloid that he had abused her and trafficked her to other men, and providing the outlet with a now famous photo of herself, Prince Andrew and Ms. Maxwell.

Mr. Epstein’s email said that Ms. Giuffre had “spent hours at my house with him” — Mr. Trump — yet Mr. Trump “has never once been mentioned.” Ms. Giuffre said in a 2016 deposition that Mr. Trump never had sex with her or even flirted with her.

In 2012, Mr. Epstein emailed one of his lawyers, Reid Weingarten, and suggested that he get someone to dig into Mr. Trump’s finances, including the mortgage on Mar-a-Lago and a $30 million loan Mr. Epstein said that Mr. Trump had received. Reached on Wednesday, Mr. Weingarten declined to comment, saying he was limited by attorney-client privilege.

As Mr. Trump’s presidential campaign gained traction in December 2015, Mr. Epstein asked Landon Thomas Jr., then a New York Times reporter, “would you like photso of donald and girls in bikinis in my kitchen”?

It is unclear whether Mr. Epstein actually possessed such photos. Mr. Thomas, who has not worked at The Times since 2019, said Mr. Epstein never provided them. Mr. Epstein also told him about a time when he said Mr. Trump was “so focused” on watching young women in a swimming pool that he bumped into a door, “leaving his nose print on the glass.”

A few months later, in March 2016, Mr. Epstein was bracing for the publication of a book, “Filthy Rich,” that detailed allegations against him. The journalist Michael Wolff, who had a longstanding relationship with Mr. Epstein, told him that he needed to serve up a “counter narrative” to the forthcoming book.

“I believe Trump offers an ideal opportunity,” Mr. Wolff wrote. “It’s a chance to make the story about something other than you.” It is unclear whether Mr. Epstein responded to the message and acted on Mr. Wolff’s advice.

A couple of months later, Mr. Wolff told Mr. Epstein that he would be interviewing Mr. Trump. “Anything you think I should ask?” he wrote.

Mr. Epstein replied with a list of “provocative” questions, including about the Trump Shuttle airline, a casino bankruptcy and his debts. “otherwise you can just throw easys,” Mr. Epstein wrote.

Mr. Wolff did not respond to a request for comment.

Mr. Epstein repeatedly insulted Mr. Trump. In a January 2018 email to Mr. Wolff, Mr. Epstein referred to the president as “dopey donald” and “demented donald,” saying that his finances were “all a sham.”

Later that year, Mr. Epstein emailed with Lawrence H. Summers, the former Treasury secretary and Harvard University president, about Mr. Trump. Mr. Epstein called him “borderline insane.”

When Mr. Summers asked whether Mr. Trump would “crack into insanity,” Mr. Epstein replied that the president’s “strength is remarkable. he is pounded 24/7. I hope someone close to him gets indicted, but not sure, otherwise the pressure of the unkown will force him to do crazy things.”

Mr. Summers declined to comment and referred to previous statements in which he acknowledged “regretting my past associations with Mr. Epstein.”

Many of the messages referring to Mr. Trump are banal. Mr. Epstein’s staff discussed whether Mr. Trump’s arrival at the Palm Beach, Fla., airport would impede the movements of Mr. Epstein’s jet. Friends and advisers frequently sent Mr. Epstein links to news articles about Mr. Trump’s political rise, his policies and investigations into his administration and allies. And associates peppered Mr. Epstein with questions about what Mr. Trump’s presidency might mean for geopolitics and financial markets.

“trump ., is scaring the markets not china,” Mr. Epstein wrote in August 2015 to an unidentified acquaintance who had asked about economic turmoil.

By late 2018, the authorities were closing in on Mr. Epstein. A series of articles in The Miami Herald showed that Mr. Trump’s labor secretary had signed off on Mr. Epstein’s 2008 plea deal. The Herald series prompted the Justice Department to open a wide-ranging criminal investigation into Mr. Epstein.

That December, Mr. Epstein was texting with an unidentified acquaintance, who wrote that “they’re really just trying to take down Trump and doing whatever they can to do that…!”

“its wild,” Mr. Epstein replied. “because i am the one able to take him down.”

The next month, Mr. Epstein wrote to Mr. Wolff about Mr. Trump and Mar-a-Lago. “Trump said he asked me to resign, never a member ever,” Mr. Epstein wrote. “of course he knew about the girls as he asked ghislaine to stop.” Mr. Trump has said that he cut ties with Mr. Epstein after he “stole” Ms. Giuffre from Mar-a-Lago, where she had worked as a spa attendant.

On June 13, 2019 — about three weeks before F.B.I. agents arrested Mr. Epstein as he got off a private plane in New Jersey — his longtime accountant, Richard Kahn, told Mr. Epstein in an email that he had just finished reviewing Mr. Trump’s federal financial disclosure form. Mr. Kahn called the form “100 pages of nonsense.” He identified nine “interesting findings” about Mr. Trump’s debts, income and charitable foundation.

It isn’t clear why Mr. Kahn was digging into Mr. Trump’s finances or whether Mr. Epstein responded to the message.

Over the preceding months, Mr. Kahn had sent Mr. Epstein numerous other emails with links to articles about topics like the investigations Mr. Trump was facing over Russian interference in the 2016 election. A lawyer for Mr. Kahn didn’t respond to a request for comment.

At other points, Mr. Epstein asked acquaintances whether they had information on the lawyers who were representing Mr. Trump. It is unclear why Mr. Epstein was asking.

Reporting was contributed by Devlin Barrett, Luke Broadwater, Andrew Chavez, Kirsten Danis, Dylan Freedman, Michael Gold, Matthew Goldstein, Will Houp, Teresa Mondría Terol and Glenn Thrush.