Report: Author Michael Wolff encouraged Epstein to blackmail Trump

By Jerry McConway, 
updated on November 13, 2025

Author Michael Wolff is obsessed with Donald Trump, and that is probably far too kind a word.

If you look at the books he has written over the last two decades, they all seem to be designed to denigrate Trump and Fox News.

Wolff also had a relationship with Jeffrey Epstein, and if recent reports are accurate, he was encouraging the disgraced billionaire to blackmail Trump.

Melania Trump

Wolff is a regular guest on leftist podcasts because they all know he will go after Trump whenever he opens his mouth.

One of Wolff’s claims was that Melania and Donald Trump had sex for the first time on Epstein’s plane.

He also claimed that it was Epstein who arranged for the two of them to meet.

This resulted in Melania Trump threatening a $1 billion lawsuit against Wolff if he did not retract his statements about her.

Countersuit

After Melania threatened legal action against Wolff, he fired right back with his own suit, stating, "Mrs. Trump's claims are made for the sole purpose of harassing, intimidating, punishing or otherwise maliciously inhibiting Mr. Wolff's free exercise of speech.”

It would appear, however, that most of what Wolff says about Trump is hearsay gleaned through his contacts with Epstein.

I say this because of his recently revealed comments about pushing the Trumps to disclose details of the relationship, stating, “To be perfectly honest, I’d like nothing better than to get Donald Trump and Melania Trump under oath in front of a court reporter and actually find out all of the details of their relationship with Epstein."

There has been little movement on his suit since it was filed, but I will say this... every person who used Wolff's account of the Trumps' relationship, save for Hunter Biden, has retracted their statements and apologized to Melania, so take that for whatever it is worth.

Blackmail

In emails that were recently leaked to the media by Democrats, it appears that Wolff was recommending that Epstein blackmail Trump. Wolff wrote Epstein regarding an interview in which Trump was to participate, stating, “I hear CNN planning to ask Trump tonight about his relationship with you -- either on air or in scrum afterwards.”

He then added, “I think you should let him hang himself. If he says he hasn’t been on the plane or to the house, then that gives you a valuable PR and political currency. You can hang him in a way that potentially generates a positive benefit for you, or, if it really looks like he could win, you could save him, generating a debt.”

Wolff had also suggested that Epstein take down Trump during his presidential campaign, writing, “There’s an opportunity to come forward this week and talk about Trump in such a way that could garner you great sympathy and help finish him. Interested?”

I don’t doubt for a second that Trump and Epstein hung out from time to time, as they ran in the same social circles. But during those years, there were never reports that Trump and Epstein were best buddies, as Epstein claimed (I lived in the same area at the time, so I definitely would have heard or seen the reports). Wolff, to me, is a dishonest writer with a grudge and a criminal conspiring solely for the sake of conspiring. I am giving Trump the benefit of the doubt here until proven otherwise.

About Jerry McConway

Jerry McConway is the Senior Editorial Director at American Digest Media, as well as the featured columnist on Real Talk Digest. He has been covering politics for more than a decade. His no-nonsense writing style makes him enemy number one in DC. His mission is to tell the truth to readers, good or bad, something the mainstream media has failed to do for decades. What sets Jerry apart from his competition is reader loyalty. They don't always agree with him, but they know he tells them the truth. Love him or hate him, you can't ignore him.

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