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Leland Nally · Jul 27, 2025

Walking and Quacking like a Pedophile

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Leland Nally · Leland Nally

In the growing backlash against the Trump administration’s refusal to release the Epstein files, newly discovered artifacts of Trump and Epstein’s mysterious relationship are being absorbed into the public consciousness—most significantly of late is the weird, nightmarish birthday letter Trump reportedly wrote to Epstein in 2003, containing a dream-like mock conversation between the two with phrases like “enigma’s never age” and “may everyday be another wonderful secret”. Alongside these newer revelations, older points of connection are being re-examined—the smorgasbord of photographs of him and Epstein and/or Ghislaine Maxwell over the years, the various quotes from Trump about Epstein in the public record (namely his 2002 comment that Epstein “likes beautiful women as much as I do, and many of them are on the younger side.”), Trump’s multiple appearances in the Epstein flight logs—just to name a few.

But resurfacing next to all of this renewed examination of Donald Trump’s past with Jeffrey Epstein is Trump’s own bizarre history of sexualizing kids. Memes and quotes containing Trump, say—telling two 14-year-old girls he’ll be dating them in a couple years—are going viral once again in light of the increasingly guilty-vibe emanating off of Donald Trump as he desperately tries to get people to stop talking about the Epstein files.

A lot of hay is made over Epstein’s connections with all kinds of famous, wealthy, powerful people and the various tracks they’ve left behind—Epstein collected over a thousand contacts in his black book, and being an inveterate socialite, ended up appearing in a lot of pictures with a lot of people. Trump defenders will tell you that they were simply both rich guys in New York at the same time, that of course they ran into each other occasionally or socialized, that (dozens of?) pictures of them together or maybe a (insanely weird, intimate, truthfully bone-chilling) birthday letter here or there is nothing. A lot of people that are photographed or otherwise superficially connected with Epstein make the same argument—what’s unusual about Trump, what makes his claim different, is not only does he seem to have been significantly closer to Epstein than the average New York or Palm Beach socialite, with significantly more points of close connection than almost anyone else, he also has his very own weird history of sexualizing children.

Even weirder, if you go back and locate these reports, you’ll notice a pattern; they line up pretty much exactly with Epstein’s presence in his life. A brief timeline:

There is something psychosis-inducing that this man is now using his authority as the President of the United States to inhibit the release of the Epstein files. The sheer obviousness of the cover-up—what Trump stands to lose and what risks to be revealed—is staggering.

As the birthday letter correctly states, Epstein and Trump had a lot in common—they were both very rich men, they were based in New York and Palm Beach at the same time, they seem to have spent a lot of time together, and they both created a reputation for themselves around flaunting their desire for young girls. Epstein famously named his plane the ‘Lolita Express’—and friends of his told me he leaned in to that reputation, that he loved the bad-boy air that being constantly surrounded by visibly young women gave him. Trump, similarly, always leaned in to his reputation for being with younger girls, at one point telling Howard Stern on air that he had to “promise” to Ivanka not to “date anyone younger than her”—she was 17 at the time.

When I called everyone in Epstein’s black book in 2020, I encountered a number of former friends and associates of Epstein’s who felt foolish and regretful about not seeing the, in hindsight, obvious ‘red flags’ in Epstein’s behavior before his arrest in 2007 (more than once, people used the idiom, ‘if it walks like a duck and quacks like a duck’). In some ways, these Epstein ‘red flags’ they spoke to me about amounted to less than some of what Trump has been reported to have said and done in the public record. Time will tell if leaving a wake of foolish regret will be another thing Trump and Epstein have in common.

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