I’m not saying that AI is entirely perfect. But this time, it’s perfectly plausible.
As you’ve probably heard by now, The Wall Street Journal is claiming that Donald Trump is one of the people who sent a “bawdy” letter to Jeffrey Epstein on the occasion of his 50th birthday in 2003. Now, of course, at the time Epstein was just a financier with a secretive source of income, not a known sex trafficker who would die in his jail cell.
However, the letters that Epstein received were put into a leather-bound album — and Trump’s alleged contribution is just now being examined as his administration grapples with how much information should be released, or is even available to be released, about Epstein’s past.
Trump said the letter was fake:
The letter bearing Trump’s name, which was reviewed by the Journal, is bawdy — like others in the album. It contains several lines of typewritten text framed by the outline of a naked woman, which appears to be hand-drawn with a heavy marker. 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.
The letter concludes: “Happy Birthday — and may every day be another wonderful secret.”
In an interview with the Journal on Tuesday evening, Trump denied writing the letter or drawing the picture. “This is not me. This is a fake thing. It’s a fake Wall Street Journal story,” he said.
“I never wrote a picture in my life. I don’t draw pictures of women,” he said. “It’s not my language. It’s not my words.”
And, to be blunt — it didn’t sound like him, either. The note is written in the third-person, for one thing, and contains a certain level of abstract weirdness that doesn’t exactly seem to match The Donald’s style:
“Enigmas never age” wrote Trump to Epstein in the birthday note, along with “We have certain things in common” and “Happy Birthday – and may every day be another wonderful secret.” https://t.co/Rsscpj9yPR pic.twitter.com/g0ufpAreFV
— Aaron Reichlin-Melnick (@ReichlinMelnick) July 17, 2025
But we’re not linguistic experts. Thankfully, we now have a tool that tries to be an expert at everything.
We asked Grok AI — which agreed with that assessment, that it’s not his. Not only that, but it gave us a more, ahem, usual suspect.
First, we asked Grok to compare the note “to everything you have on Trump’s typical prose and conversational styles, paying attention to word choice, syntax, and lexicography specifically. Use what you have from his books, his speaking style on the Apprentice, and his speaking style when interacting with individuals.”
After comparing it, we asked its to assign a percentage likelihood that Trump wrote it.
That likelihood: 15 percent.
For instance, take word choice. First, Trump’s typical style:
Simple, boastful: “I like thinking big. I always have.” (Art of the Deal). Superlatives like “tremendous,” “best.” In private calls: “You have to dominate … They’re going to run over you” (2020 governors call). Avoids abstract nouns; focuses on “winning,” “deals,” “money.
Then, the alleged note:
Cryptic and abstract: “Enigmas never age,” “wonderful secret.” Uses “pal” (old-fashioned, friendly but not typical Trump slang—he prefers “friend” or “buddy”). “Enigmas” is sophisticated and metaphorical, rare in Trump’s lexicon.
This, Grok said, was a “low match.”
Trump’s vocabulary is plain and repetitive, not enigmatic or poetic. “Enigmas’” feels out of place — he uses words like “disaster” or “loser” for emphasis, not riddles. The closing wish (“may every day be another wonderful secret”) is whimsical and indirect, unlike his blunt style.
Furthermore, Grok determined the overall tone and prose was a “strong mismatch.”
Trump’s prose is straightforward and boastful, not veiled or humorous in a mysterious sense. He avoids subtlety, preferring direct assertions. This feels more like scripted wit than his off-the-cuff, ego-centric ramblings. …
While Trump can be informal in private, the cryptic, riddle-like quality doesn’t align with his simple, repetitive, dominance-focused style. To arrive at this: I cross-referenced ~50 excerpts/transcripts for patterns (e.g., vocabulary frequency: superlatives appear 10x more than abstract terms). If it were Trumpian, we’d see repetitions, boasts, or tangents—not balanced, mysterious exchanges. This is a qualitative estimate grounded in linguistic evidence, not absolute probability.
OK, then — so if not Trump, then who? An assistant, perhaps. Or maybe another known pervert like Harvey Weinstein or Sean “Diddy” Combs. But as long as we had Grok on the line, we asked it if it sounded like someone else, perhaps someone who also knew Epstein.
In fact, it appears Epstein had a painting of one of the prime suspects:
Reminder:
This painting of Bill Clinton was hanging in Epstein’s NYC apartment. pic.twitter.com/vpG9jKuXxA
— Glockford Files (@GlockfordFiles) July 8, 2025
That’s right! Here’s what Grok said about the match-up with Slick Willy’s style: “Known for charismatic, conversational rhetoric with a knack for personal charm. In private, he’s witty and anecdotal, as seen in memoirs like My Life (2004): ‘I learned a lot from that old man about human nature.’ His public interviews (e.g., 2000s TV appearances) show a playful, engaging tone, often with suggestive humor. Private correspondence (e.g., emails released later) uses informal, friendly language (‘friend,’ ‘buddy’) but rarely cryptic phrasing.”
Bill Clinton was quite the pal of Jeffrey Epstein.. Bill went on a month-long (!) vacay with Jeffrey, once .. and took 4 flights with Jeffrey — one to Europe, one to Asia, and two to Africa.. imagine that. 🤔🤔🤔🤔 pic.twitter.com/Y3qJAVOQXa
— Phil Free (@Whachutryin2say) July 8, 2025
Is the Trump-Epstein birthday note real?
Another possibility was filmmaker Woody Allen, whose personal creepiness needs to expounding. Grok’s reason for finding a “strong match” between the text and the “Annie Hall” filmmaker: “Rapid-fire wit, clever one-liners, philosophical musings, funny wordplay, and cryptic humor. Dialogues often feature enigmatic, metaphorical language with a playful, evasive tone … Incorporates slang origins and emotional insights through abstract expressions.”
“The style best suits someone with a creative, metaphorical bent like Woody Allen, whose work thrives on enigmatic humor — making him the strongest stylistic match among prominent Epstein-linked figures.”
Now, again, take this as you will: This is the same model that my editor recently used to create a picture of an otter strumming a ukulele — and, as we all know, otters strongly favor woodwinds when expressing themselves musically.
However, one is inclined to believe an AI analysis that this doesn’t pass a smell test because it doesn’t pass a human smell test, either. The only way this alleged Epstein note could possibly sound less Trumpian is if it ended with, “So we beat on, boats against the current, borne back ceaselessly into the past.” And given that F. Scott had been dead for 63 years before the “bawdy” Epstein note was written, that’d eliminate him, too.
And, while textual analysis isn’t dispositive as to who it really is if this were a fake, all I’m saying is that Jeff Epstein didn’t have paintings of either Donald Trump or Woody Allen in a blue dress in his Manhattan townhouse. Just a thought.
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