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How Big An Issue for Trump is Jeffrey Epstein?

How Big An Issue for Trump is Jeffrey Epstein?

Answering your questions!

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Gabe Fleisher
Jul 20, 2025
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Wake Up To Politics
Wake Up To Politics
How Big An Issue for Trump is Jeffrey Epstein?
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Happy Sunday, everyone! Welcome back to another Q&A column. This week, we’ll tackle:

  • How much the latest Epstein developments will hurt Trump

  • How previous presidents have used the rescissions process

  • An update on Trump and complying with court orders

  • How Trump always manages to persuade GOP lawmakers

And more!

Trump and Epstein

Q: What’s your take on the Epstein-Trump “enigmagate?” I am seeing all types of pundits out there saying “this is different” and that MAGA is turning against Trump—but I can’t help but feel I’ve heard this all before with J6 and tariffs, etc.

Q: Do you think that Trump’s supporters will back down on the Epstein situation? How important is this for the Democrats at the mid-terms?

For those who haven’t followed every twist and turn of this, “Enigmagate” is a reference to the recent Wall Street Journal report (gift link) that Donald Trump sent a letter to Jeffrey Epstein for his 50th birthday, which included a drawing of a naked woman and some pretty cryptic phrasing, like “Enigmas never age” and “May every day be another wonderful secret.”

Definitely weird.

Since Trump is denying the report (and even suing the Journal over it), I should state up front: I see no reason not to believe the story, which was reported by a pair of trustworthy journalists (one of whom previously broke another big story about Trump’s personal life) and by an outlet that wouldn’t have printed something like this unless they were sure. (Key parts of the Trumpworld denial — like the idea that Trump doesn’t doodle or say the word “enigma” — have also been proven false.)

Of course, that doesn’t mean anything will come of the story.

Personally, with all the hype around the story before it dropped (including reports that Trump tried hard to prevent its publication), I was expecting something more. Of course, in abstract, it’s damning that the president would have been so friendly with someone who was later arrested for sex trafficking — but we have already known that for years. The letter, though odd, was written cryptically enough that it didn’t really produce anything of substance that we didn’t know about the relationship.

(The Trump/Epstein anecdote I have found most 👀 👀 recently — which was not new, but new to me — was this, from the New York Times: “When Mr. Trump hosted a party at Mar-a-Lago for young women in a so-called calendar girl competition, Mr. Epstein was the only other guest, according to George Houraney, a Florida-based businessman who arranged the event.”)

So where does that leave us politically?

Well, if you look at this chart from the polling analyst G. Elliott Morris, the Epstein Files looks like Trump’s most glaring vulnerability. More than 40 points underwater!

But I think there’s something big this chart leaves out.

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