Update News: July 21, 2025

Does Trump's alleged letter to Epstein "sound like" Trump? An investigation.

Judd Legum

Jul 21, 2025

On Thursday, the Wall Street Journal published a bombshell report about President Trump's relationship with convicted pedophile Jeffrey Epstein. According to the Journal, the materials collected as part of the Department of Justice's investigation into Epstein included a 2003 birthday message from Trump to Epstein.

Trump's alleged message consists of "several lines of typewritten text framed by the outline of a naked woman, which appears to be hand-drawn with a heavy marker." The drawing, which the Journal describes as "bawdy," includes "[a] pair of small arcs denotes the woman’s breasts, and the future president’s signature is a squiggly “Donald” below her waist, mimicking pubic hair." Inside the figure of the woman was the following text:

Voice Over: There must be more to life than having everythingDonald: Yes, there is, but I won’t tell you what it is.Jeffrey: Nor will I, since I also know what it is.Donald: We have certain things in common, Jeffrey.Jeffrey: Yes, we do, come to think of it.Donald: Enigmas never age, have you noticed that?Jeffrey: As a matter of fact, it was clear to me the last time I saw you.Donald: A pal is a wonderful thing. Happy Birthday — and may every day be another wonderful secret.

Trump told the Journal that the letter is "fake" and quickly sued the paper, its owner Rupert Murdoch, and the two reporters who wrote the story for $10 billion. On Truth Social, Trump insisted that the letter is "not the way I talk."

Meanwhile, numerous allies of the president have echoed this claim, arguing that the letter is inauthentic because its language does not sound like Trump. "Does anyone honestly believe this sounds like Donald Trump?" Vice President JD Vance asked rhetorically on X. White House Press Secretary Karoline Leavitt said the letter published by the Journal is "not at all how he speaks or writes." Trump's eldest son, Donald Trump Jr., said it is obvious the letter is inauthentic because it doesn't match his father's "very specific way of speaking."

To evaluate these claims, Popular Information examined the most distinctive aspects of the letter and assessed whether they are consistent with Trump's history.

Would Trump use the word "enigma"?

The most distinctive single word in the letter is "enigma." Is it plausible that Trump, known for using simple language, would use that word?

Trump's defenders do not believe so. "I find it to be an enigma that Donald Trump would use the word enigma," billionaire Bill Ackman, a prominent Trump supporter, wrote on X. Sean Davis, the CEO of the right-wing publication The Federalist, posted that he asked Grok, the chatbot created by xAI, to "search every record of Trump speaking or writing" for the word "enigma" and determined "there is no record of him ever saying or speaking the word." (Trump Jr. also reposted Davis' claim.)

Davis' confident assertion is false and demonstrates the hazards of relying exclusively on AI tools for research. In 2015, Trump used the word "enigma" twice to describe Ben Carson, one of his Republican primary opponents. "Now, Carson’s an enigma to me," Trump said. "Carson’s an enigma."

Trump also used the word "enigma" twice in his 2004 book, Trump: How to Get Rich. "Dan Rather is an enigma to me," Trump wrote on page 166. He uses enigma again on page 55, writing that entrepreneurial skills are "one of those grey areas that remain an enigma even to those with finely-honed business instincts."

Trump also used the term in his 1990 book, Trump: Surviving at the Top. "Any discussion of Mike’s affairs eventually leads to the subject of Don King," Trump wrote about Mike Tyson on page 200. "Don, like Mike, is something of an enigma."

So, while enigma is not a commonly used word, it is one that Trump has deployed in a variety of contexts for many years.

Would Trump have called Epstein his "pal"?

The word "pal," which appears at the end of the letter to Epstein, is somewhat old-fashioned and less commonly used than the more straightforward term "friend." Trump, however, has used "pal" over the years to describe his close associates.

In a 2018 roundtable on tax reform, Trump talked about his friendship with Steve Witkoff, who is currently Trump's special envoy to the Middle East. "He's become a very wealthy, successful man," Trump said. "And he's my pal." During a 2011 speech to the Nevada Republican Party, Trump referred to developer Phil Ruffin as "my pal."

Would Trump have been familiar with Maurice Sendak?

Perhaps the most distinctive characteristic of the letter is the opening line: "There must be more to life than having everything." This is a direct quote from Higglety Pigglety Pop!, a classic 1967 book by children's author Maurice Sendak. It comes off like an inside joke between the two men.

Sendak and Trump have a history. In 1993, Sendak published We Are All in the Dumps with Jack and Guy. The book, which stirred controversy due to its exploration of weighty topics such as the AIDS crisis, garnered extensive coverage in the national media, including The New York Times, Los Angeles Times, and The Palm Beach Post, the local paper for Mar-a-Lago. It also featured a direct attack on Trump, with one illustration featuring homeless children against the backdrop of Trump Tower. The children exclaim, "Tricked. Trumped. Dumped!"

A September 5, 1993, story in the New York Times highlights Sendak's criticism of Trump. The reporter, Degen Pener, said he reached out to Trump for comment. (Trump did not respond.)

Trump is a voracious consumer of media, especially when it involves him, so he almost certainly would have read the coverage of Sendak's book. The fact that the New York Times, a paper Trump follows closely, reached out to him increases those odds further.

The timing of the incident, 1993, coincides with a period during which Epstein and Trump were known to socialize together regularly.

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