Epstein Files May Give ‘Blackmail’ a Whole New Meaning

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This may be the understatement of the year: Something deeply untoward appears to be hidden just beneath the surface of recently released documents as they relate to certain people.

I’m referring to those that keep emerging on billionaire investor Leon Black’s relationship with Jeffrey Epstein — and how they involve Donald Trump.

To be sure, pretty much everyone mentioned in these documents has made the standard disclaimer: They did nothing wrong, did not participate in his wrongdoing, did not even know about it. And, in some cases, that is true. 

But certain things about Black are also true. The most salient point, to me, is that Trump — so well known for being transactional — seemingly rewarded Black, for something, by unexpectedly appointing his son Benjamin to a significant administration post. 

In the early days of Trump’s second term, the high-flying investment firm Black co-founded, Apollo Global Management, showed interest in taking on a big chunk of the huge debt Elon Musk had incurred in buying Twitter. This occurred while Musk and DOGE were front and center in the Trump administration, centerpieces in Trump’s “showing results” to his base. Musk had also, of course, just pulled out all the stops to get Trump elected; his heavy independent spending in swing states is believed to have contributed to Trump’s victory.

Shortly after a news report on the Apollo interest in Musk’s debt, Trump appointed Black’s son CEO of the US International Development Finance Corporation (DFC). It’s interesting to note that Benjamin Black had not been one of the names bandied about for the position.

Right after this appointment, Apollo purchased an unspecified but clearly substantial amount of Musk’s debt.  

Normally, one might simply assume that Black was doing Trump a favor because Trump was president; getting on his good side would make sense. And Trump is no stranger to quid pro quo. 

However, one needs to consider that Black, who had to leave his roles as CEO and chairman of Apollo over the mess back in 2021 (when Black’s relationship with Epstein was being scrutinized) faces potential continuing legal, financial and reputational peril.

And that’s where the following seems so important: 

Treasury Secretary Scott Bessent, not known for taking major actions without Trump’s assent, has refused to release documents relating to Black and Epstein — in particular, SARS (Suspicious Activity Reports) on huge sums Black sent to Epstein. (SARS are documents filed by financial institutions to inform government agencies of potentially illegal activities.)

Sen. Ron Wyden (D-OR) is currently investigating Black for allegedly paying Epstein between $158 and $170 million — ostensibly for tax and estate-planning services. Wyden questions whether those enormous, outsized sums were truly for legitimate professional services or played some other role. To determine that, he very much needs those SARS.  

In a clumsy, fumbling attempt to distract from his withholding those crucial documents, last August, Bessent very blatantly tried to shift suspicion to Wyden, seemingly out of thin air.

Instead of producing the Black-Epstein information, he pivoted to asserting that Wyden is “very rich” and may be guilty of insider trading — and claimed, seemingly with zero basis, that there may be SARS on Wyden. Wyden slammed him back:

Scott Bessent doesn’t like that I revealed that he’s sitting on a massive Epstein file, so he’s resorting to making ridiculous accusations. https://t.co/oN1bWmzC96

— Ron Wyden (@RonWyden) August 13, 2025

Epstein seems to have been closer with Black than almost anyone else, except possibly Trump — whom Epstein once referred to as his “best friend.” Black first met Epstein in 1996 and found him to be a “fascinating guy.” They lived two blocks apart on New York’s Upper East Side and on numerous occasions had breakfast, lunch, and dinner together at Epstein’s town house. 

Black also visited Epstein’s island in the Caribbean, and he once flew with two of his children on Epstein’s jet to Boston to visit Harvard and MIT. In 2011, the two men invested in a firm (Environmental Solutions Worldwide), and two of Black’s sons served on the company’s board. It was all very chummy until 2018 when Black cut relations with him over a fee dispute. 

A lawsuit alleges Black raped a 16-year-old girl (“Jane Doe”) in Epstein’s townhouse in 2002. His lawyer claimed the charges were “totally made up, entirely uncorroborated and, as pleaded, squarely violate the statute of limitations.” The alleged victim’s law firm withdrew from the case in 2025. Another alleged victim accused Black of rape in 2002, also in Epstein’s town house, and she, too, withdrew her case.

With Epstein dead, Black is one of the few people who might know more than anyone else alive about things Trump would not want made public. Which could potentially explain what Trump wants in return for his many favors to Black: specifically, Black’s continued silence.   

At a time when Republicans hope to shift the Epstein focus to the Clintons, it’s worth contemplating that yet another friend of Epstein was Howard Lutnick, whom Trump appointed commerce secretary. Lutnick claims he’d had “limited interactions” with Epstein. But documents show they were actually business partners as recently as 2014, well after Epstein was convicted and served time on Florida sex-trafficking charges.

Written on the Wind

Looking through the Epstein files, one is struck by the absence of emails from or to Trump himself, which contrasts with the two men supposedly having been best friends, and other evidence of their heavy interactions over many years. 

This absence may be explained by one of the lessons Trump is said to have learned from his gangster friends: Don’t put anything in writing. He was once seen actually eating a note after a meeting — presumably not because he was hungry. Indeed, Trump’s choice comments below explain why: 

Half of my friends are under indictment right now because they sent emails to each other about how they’re screwing people.

I go to court and they say produce your emails. I say I don’t have any emails. The judges don’t even believe it. … After you win the case, they say, “Now I know that you’re really smart.”

Related: Mueller’s Problem: Trump Eats Evidence for Lunch 

At some point, it seems to have dawned on Epstein that this was a problem for him in his long game of high stakes influence-peddling: Without written evidence he simply didn’t have the leverage he needed to keep his fish on the line. This may explain why he started writing notes to others, especially his longtime confederate Ghislaine Maxwell — getting down, “for the record,” things he was claiming he had on Trump and several others whose closeness with Epstein was sometimes not adequately documented in messages. 

Among the documents recently released are Epstein’s emails, and drafts of emails, apparently written with the intent of letting the recipients know what dirt he had on them. In a message he drafted to Bill Gates, for instance, he referred to “morally inappropriate” work he did for him, including procuring antibiotics “to deal with consequences of sex with Russian girls” and arranging “illicit trysts, with married women.” In emails to Leon Black badgering him for millions of dollars, he threw in a mention of his work structuring payments to a woman who had accused Black of sexual assault. 

He usually did this after a falling out with the person, who was no longer useful to him but who might be tempted to cooperate with investigators looking into Epstein’s affairs

Especially intriguing is an email he wrote to Ghislaine Maxwell in 2011, in which he seemed to be “informing” her of something she already knew. As I previously noted, this appears as if he was trying to create a paper trail — one that would lead back to Trump.

I want you to realize that that dog that hasn’t barked is trump – [VICTIM’S NAME REDACTED] spent hours at my house with him… he has never once been mentioned.  Police chief, etc.  im 75% there…

In 2011, Epstein was getting a lot of bad attention after the scandal involving Prince Andrew, and may have feared more. After a falling out with Trump, someone made an anonymous call about Epstein to the police in Palm Beach, FL, and not long after, Epstein was arrested. Based on growing animus between the two, Epstein had reason to wonder if that tipster might have been none other than Trump himself. So, for his protection, he may have been trying to create a written record of Trump’s own complicity in the sexual abuse of minors.

Despite Jeff Bezos

Everyone is all over Jeff Bezos’s gutting of a third of The Washington Post staff. Everyone pays lip service to the need to support the paper. But a lot of people canceled their subscriptions to penalize Bezos for blocking the paper’s endorsement of Kamala Harris and his insistence that the editorial pages do more to embrace conservative positions. Those protest cancellations were honorable. Yet the unintended consequences were perhaps to justify Bezos’s continued evisceration of a long-time gem of US journalism. 

One thing we don’t see enough of, notwithstanding all the statements of support for the institution and its staff, are concrete reminders of just how good and important the paper’s work still is. We might not find it perfect, but hardly a day goes by when I don’t see something of importance and interest there that I read nowhere else. In fact, at a moment when The New York Times seems to be surging to new levels of readership and profitability, I personally find, on a day-to-day basis, that the Post is as much, and sometimes more, of an essential read. 

One example of the kind of things Post reporters keep unearthing is how the Department of Homeland Security is targeting Americans with a secretive legal weapon few have heard of. Called administrative subpoenas, they are being leveraged in surprising ways that threaten ordinary people’s rights — including the right to free speech. It’s yet another one of so many cudgels Trump has used to spread fear and suppress opposition to his power grabs. 

I find that the Post, perhaps because it’s based in Washington, looks deeper into legislative and administrative material and processes, and makes them accessible to a general audience. 

Here’s another such story: It’s about ICE spending hundreds of millions of dollars for so-called “skip tracing services” to find the undocumented. Skip tracing is more commonly thought of as tracking down individuals who owe money; perhaps they defaulted on a loan. But here, they’re utilizing the same method to track down people who may not owe anything: 

The program creates a nationwide force of plainclothes, nongovernment monitors to track and photograph immigrants on behalf of ICE. According to the filings, the initiative is intended to serve as a force multiplier for ICE, potentially helping to accelerate the agency’s raids and deportations this year.

Final Thoughts

As good as the Post and Times can be, legacy media organizations largely opt to stay away from Trump’s accelerating mental decline, so they dance around it, creating a false appearance of normalcy. You’ve heard about him promoting a foul racist meme about Barack and Michelle Obama. But the craziness keeps on coming. 

Here’s just the latest in a string of derangement indicators: As first reported by Punchbowl, Trump told Senate Minority Leader Chuck Schumer that he’d be open to restoring funding for a major Hudson River Tunnel project — but only if at least two transit hubs, Washington’s Dulles International Airport and New York City’s Penn Station — were renamed after himself. 

I remember being in Romania right after the dictator Nicolae Ceaușescu was deposed. Journalists gleefully reported, again and again, all the signs of excess and megalomania. A former employee of his told me Ceaușescu at one point had more than 100 houses and had taken over a zoo for his personal use. Then, of course, there is Caligula, who kept his horse in a marble stable with an ivory manger, adorned him with a purple blanket and a collar of precious stones, and had him fed oats mixed with gold flakes. 

Today, that aspect of the president is widely known but somehow cannot be brought front and center for public discussion. It alone disqualifies Trump as a leader — and explains so much else that is transpiring: He’s nuts.