President Trump is grappling with a new disclosure of Jeffrey Epstein-related material that hit him much harder than the initial batch of documents released last week.

The new tranche of almost 30,000 items released late on Monday was worse for Trump in part simply because the president’s name was mentioned more frequently.

But the second round of disclosures also raised new questions about a Trump narrative that has tended to play down the president’s association with the disgraced financier and sexual predator, who died of an apparent suicide in 2019 while awaiting trial.

Trump has never been accused by law enforcement of criminal acts relating to Epstein, and he vigorously denies any wrongdoing. His previous friendship with Epstein is a matter of public record but appears to have ended around 2004. Different explanations have been given about the exact reason for their estrangement.

Skeptics will wonder about the timing of the new release, which the Department of Justice (DOJ) announced as public attention in politics ebbs and the holiday season hits its peak.

When the first batch of material emerged amid a higher level of expectation, there was little mention of Trump. In that instance, White House officials instead emphasized several photographs of former President Clinton.

A Clinton spokesperson on Monday called for the full release of all the Epstein files, saying in part: “Someone or something is being protected. … We need no such protection.”

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Perhaps the single most intriguing item relating to Trump to emerge in the second round of disclosures was an email from 2020. The email, apparently sent by a federal prosecutor in the Southern District of New York, warned an unnamed recipient about the frequency with which Trump had traveled on Epstein’s private jet in the 1990s.

“The flight records we received yesterday reflect that Donald Trump traveled on Epstein’s private jet many more times than previously has been reported (or that we were aware),” wrote the assistant U.S. attorney, whose name has been redacted.

The same email referenced one flight on which Trump and Epstein were the only passengers, and another where the only listed passengers were the two men and a “then-20-year-old” whose name has also been redacted.

Trump’s defenders note this is not incriminating in itself, nor does it add anything substantively new to the public’s knowledge, in part because more has been learnt about the Epstein flight logs between 2020 and now.

But questions are nonetheless raised by the email’s reference to the two men traveling with an anonymized 20-year-old, and the reminder that the flights were more frequent than Trump had once indicated.

Those were not the only disclosures to raise eyebrows.

Another was a subpoena sent to Mar-a-Lago in 2021 in relation to the case against Epstein accomplice Ghislaine Maxwell. Maxwell was ultimately found guilty on sex trafficking charges and sentenced to 20 years in prison. The subpoena provided almost no further specific information.

Investigators in a separate matter appear to have found a photo of Trump and Maxwell on a phone belonging to Steve Bannon in 2021, according to another email from the latest batch of documents.

The DOJ sought to blunt the impact of the new release. In a posting on the social platform X, the department asserted that “some of these documents contain untrue and sensationalist claims made against President Trump,” and implied that some false accusations had been made in the hope of influencing the 2020 presidential election.

The DOJ’s post continued: “To be clear: the claims are unfounded and false, and if they had a shred of credibility, they would have been weaponized against President Trump already.”

The controversy deepened on Tuesday afternoon when the DOJ said a potentially explosive letter, ostensibly from Epstein to the infamous pedophile Larry Nassar, was “FAKE.”

The letter, which included the suggestion that Trump “shares our love for young, nubile girls,” caused an instant firestorm on social media.

But the DOJ gave its reasons for believing the letter was a hoax, saying that the handwriting did not match Epstein’s; that it was postmarked in northern Virginia three days after Epstein’s death in New York; and that the return address neither listed Epstein’s jail nor included his inmate number which, per the DOJ, “is required for outgoing mail.”

As of early Friday evening, Trump had not commented directly on the new disclosures, and the statements from the Department of Justice appeared to be the main prongs of the administration’s response.

On Monday, Trump offered a somewhat surprising quasi-defense of Clinton in relation to the photos that had emerged in the previous batch of material.

“I don’t like the photos of Bill Clinton being shown,” Trump said, before expanding on his point by saying that other people who merely were socially acquainted with Epstein were having their reputations tarnished.

“You probably have pictures being exposed of other people that innocently met Jeffrey Epstein years ago,” Trump said.

Trump also contended on Monday that the media’s focus on Epstein was intended to “deflect from the tremendous success” of the GOP.

But questions are mounting along with the disclosures.

On Tuesday, Senate Minority Leader Chuck Schumer (D-N.Y) raised the issue of why the new documents alluded to 10 alleged co-conspirators of Epstein, yet these people had not been identified or charged.

There are plenty more disclosures to come before all the material on Epstein is released.