The Private Thoughts of a Disgraced Financier: When Epstein Weighed In on Trump

In the swirling vortex of legal dramas and public intrigue surrounding the late Jeffrey Epstein, another curious detail has emerged from the shadows: a private email, penned by Epstein himself in 2015, offering a truly candid, one might even say startling, assessment of Donald Trump. And what an assessment it was, honestly.

Addressed to none other than high-profile attorney Alan Dershowitz, the email saw Epstein label Trump as "borderline insane." But he didn't stop there. Oh no. The now-disgraced financier went on to describe Trump as a "cartoon character"—a pretty striking visual, you'd have to admit—and, quite pointedly, suggested that Trump's ultimate aspiration was, in fact, to be a "mafia boss."

This particular piece of correspondence, unearthed recently, didn't just appear out of thin air. It surfaced as part of an ongoing civil defamation lawsuit. Specifically, it's tied to the legal battle initiated by Virginia Giuffre against Dershowitz. Now, for his part, Dershowitz has maintained that Epstein was, in essence, trying to manipulate him, and that the financier was in the process of recanting earlier, unfavorable statements made about the lawyer. It's a complicated web, as these things often are, and this email adds yet another knot.

But here's where it gets even more fascinating, even a little contradictory, you could say. Fast forward to 2019. In a deposition, under oath, Epstein was questioned directly about these very sentiments. Did he call Trump "insane"? Did he refer to him as a "cartoon character"? His answer then was a firm denial. He stated, quite clearly, that he had never used such language to describe the former president. A stark contrast to the private thoughts he shared with Dershowitz just a few years prior.

It really makes you wonder, doesn't it? What prompted the initial blunt assessment? Was it a moment of genuine candor between two men? Or was there, as Dershowitz suggests, a more strategic, manipulative game afoot? And then, of course, the later retraction—was that a convenient memory lapse, or a deliberate attempt to reshape a narrative, perhaps to protect himself? The layers of complexity surrounding Jeffrey Epstein, and indeed the powerful figures who orbited him, truly never cease to amaze. This email, in truth, just peels back one more.