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The Epstein story, on which I’ve been writing for years, has exploded in recent days, and I want to provide you with some perspective on the massive trove of newly released emails. 

The biggest “news” to emerge has been Jeffrey Epstein’s mentions of Donald Trump. These have significantly increased the political vulnerability of a politician who has proven almost uniquely resistant — thanks in part to the heavily funded media operation behind him — to any sort of negative disclosure or criticism, no matter the magnitude of his alleged misbehavior. 

The new Epstein-Trump linkage leads in many directions, but for now I want to focus on a specific line of inquiry: Why Epstein was messaging others about Trump. 

As you probably know by now, in 2011, Epstein emailed his associate and sometime-girlfriend Ghislaine Maxwell about Trump — specifically stating that Trump was more deeply involved in and knowledgeable about Epstein’s sexual abuse mill than the public understood. Epstein wrote that Trump knew exactly what Epstein was up to — moreover, that Trump himself spent “hours” with at least one of the victims at Epstein’s home. 

To sort out why Epstein was even talking about Trump, we first need to review the context of what was going on at that time — most of which had nothing to do with Trump.

Jeffrey and Andrew

Epstein emailed gratuitously to burnish his image as well-connected, but it’s unclear why he mentions certain people or events, or whether he’s joking, careless, or deliberate.

Epstein’s early 2011 emails reveal his anxiety over a growing scandal, a new threat coming years after he received a mere wrist slap for sex crimes, partly because evidence was “scarce” and partly because former Florida US attorney Alexander Acosta claimed he was warned to back off, since Epstein was “with intelligence.” 

This time it wasn’t going to be so easy. A former “masseur” in Epstein’s retinue, Virginia Giuffre, had gone public with explosive allegations about Epstein and an even bigger name, then-Prince Andrew of the United Kingdom. 

Giuffre said that Epstein and Maxwell had introduced her — when she was a minor — to Andrew, who, she claimed, sexually abused her. A now-infamous photo of Andrew and Giuffre together was published in a UK newspaper that February.  

This was cataclysmic for the royal family, coming as another in a long line of scandals rocking the palace in recent decades. 

Among the vast trove of documents was a March 2011 email in which Andrew repeatedly pleaded with Epstein and Maxwell, who had originally introduced them, to help him out of a rapidly worsening situation. 

The royal wanted them to assert, emphatically, that he had no involvement in the alleged activities. He said that the coverage was destroying him. 

Roughly a month later, Epstein referenced the “dog that didn’t bark” — a term from the 1892 Sherlock Holmes short story “Silver Blaze” — in the email to Maxwell: 

I want you to realize that that dog that hasn’t barked is Trump… [REDACTED] spent hours at my house with him… [yet] he has never once been mentioned…

Was Epstein, either on his own or under pressure from at least one member of the beleaguered British royal family, pondering a way to divert attention from Andrew to Trump? We do know that he tried to destroy the credibility of Giuffre — who had supplied the original photo of Andrew with his arm around her to the FBI in 2011.

Also, please note the cryptic reference to a “police chief” in the above email. We’ll come back to it. 

Discrediting Virginia Giuffre

In that same period, Epstein was quickly ramping up a PR campaign to protect himself — and the royal family. 

On July 1, 2011, Epstein sent messages to two prominent figures in the media ecosystem that contained numerous demonstrable lies about Giuffre.

Epstein asked the well-connected publicist Peggy Siegal to reach out to Arianna Huffington, founder and editor of the then-influential Huffington Post, and encourage her team to investigate Giuffre. 

The same day, he wrote Landon Thomas Jr., a reporter at The New York Times, and pushed a similar line about Giuffre:  

In both missives, he mentioned the British royal family and its concerns. 

But why, as Epstein faced new legal peril from fresh allegations, was he writing to Maxwell about Donald Trump and emphasizing Trump’s involvement in his activities?

Was it because Trump had allegedly done the same things of which Prince Andrew was accused?. 

Epstein’s 2011 email makes sense in this context. Although the House committee redacted the victim’s name, it seems likely he was referring to Giuffre. If true, his claim that Trump personally spent hours with her, presumably in a sexual context when she was 16, is profoundly consequential even years later.

If in fact Epstein was telling the truth about that incident, how would revealing it have helped Andrew — or Epstein? 

To be sure, today, with Trump as president, this is big news. But back then, Trump was “just” a famous businessman and reality TV star, and his presidential prospects were beyond remote. 

Trump the ‘Rat’? 

One reading of Epstein’s language suggests he suspected that Trump, a former friend with whom he had fallen out in 2004, was feeding allegations to the authorities. As noted, in the “dog that didn’t bark” email, Epstein wrote:

Police chief, etc. I’m 75% there

What was that about? Based on the context, it seems to refer to Trump and, probably, to the following fact: Soon after their falling out after Trump outbid Epstein on a seaside mansion (Trump also claimed that Epstein “stole” staff from Mar-a-Lago, including the young Giuffre), someone made an anonymous call about Epstein to the police in Palm Beach, FL. 

If Epstein believed that Trump was his biggest threat, Epstein would have been highly motivated to push back at Trump and, moreover, to do so by bringing out Trump’s own complicity in the sexual abuse of minors. 

But why specifically email Maxwell — who seemed to know more about everything than anyone but Epstein himself — and introduce the subject with the words: “I want you to realize…”? 

Epstein was no dope, and understood that sending emails, however coded and cryptic, creates a trail which might be followed by law enforcement and the media.

As for Trump, we know that he maintained a “leaker” relationship with media outlets and with law enforcement to advance his business interests, serve his ego, and damage perceived enemies. He is believed to have had a quasi-informant relationship with the FBI, a la “Whitey” Bulger, in the years when Trump’s buildings swarmed with mobsters, Russian tycoons, and the like. Was he dishing on Epstein in that capacity? 

Did Trump think that, despite — or even because of — his knowledge of Epstein’s operation, he would be immune himself? Presumably, the FBI would prevent the release of any documents in its possession showing Trump himself ratting out others. 

In subsequent years, as Trump’s presidential aspirations went from joke to jackpot, Epstein became increasingly alarmed and outspoken in his messages about his contempt for Trump. He also seemingly grew worried and indignant that despite the dirt he had on him, Trump was ascendant and possibly invincible. Still, he must have long understood that he and his former brother-in-lawbreaking would end up in a Death Star battle. 

Flash forward to the present and consider this turnabout: Epstein dies (“commits suicide”) in a federal facility ultimately controlled by Trump. Maxwell, also in federal prison and at Trump’s mercy (via the presidential pardon power), is cooperating by clearing him of any allegations. 

This situation of course thrilled Trump’s backers — and pro-Trump media promoted Maxwell’s dubious and self-serving statements as the best hope for bailing Trump out of the one scandal that keeps on sticking. 

That is, at least, until this new batch of documents was released. Suddenly, Maxwell’s much celebrated “clearing of Trump” — at the price of a transfer to a cushy minimum security prison and the possibility of a pardon — is worth less than nothing.

For years, Trump held all the cards in his battle with Epstein. But will a dead man have the last laugh? 

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