Jeffrey Epstein’s Inbox Was A Place To Complain, Talk Shit, And Make Boomer-Grade Jokes

Poking through the 20,000-plus pages of emails from Jeffrey Epstein's inbox that were released by the House Oversight Committee last week can be a destabilizing experience. If there's one exchange that best evokes the sickly feeling that comes from spending too much time reading these emails, it might be Epstein writing to Silicon Valley vampire Peter Thiel about future plans to meet up and asking, "any interest in woody allen?" to which Thiel responded, "Would be cool to meet him sometime, but don't go out of the way to make this happen..."

But when he wasn't coordinating nightmarish dinner parties, Epstein spent time sending and receiving the kinds of emails you'd expect to find in the inbox of any boomer with a suspect grasp on reality. Context-free links to news articles are abundant, as are staggering typos, genuinely stupid musings, an obsession with Donald Trump, and mundane shit-talking. Below is a representative selection of what Epstein and his pals liked to chat about over email. Each email exchange should be read bottom to top for proper chronology.

Epstein frequently corresponded with Kathryn Ruemmler, who was previously White House Counsel for Barack Obama and is currently general counsel for Goldman Sachs. They liked to talk about politics, and developed a frankly ludicrous recurring bit about how Donald Trump reminded them of the TV character MacGyver:

They went back to this well several times, without ever settling on an agreed-upon spelling for MacGyver:

On another occasion, Epstein emailed Ruemmler to tell her, "talking to macgiver, disturbs me, and that takes a lot." This conversation eventually led to Epstein referencing an apparent falling-out with Bill Clinton:

In another thread, a stray observation about Trump led to Ruemmler revealing some internal anxieties:

Ruemmler and Epstein weren't always on the same page, though. One exchange began in typical fashion—with Epstein sending Ruemmler a link to a news article about former Trump White House advisor Steve Bannon he described simply as "fun"—and ended with Ruemmler taking exception:

Speaking of Bannon, this cache of emails reveals that he and Epstein maintained a robust correspondence throughout the first Trump administration. What kind of stuff did they like to talk about? Pretty much what you'd expect. For example, here's Bannon and Epstein looping in Michael Wolff to complain about Ta-Nehisi Coates being one of the judges who awarded the Miami Herald a 2019 Hillman Prize for its reporting on Epstein:

And here is Epstein testing Bannon's knowledge of Adolf Hitler's biography before making a self-deprecating joke about his status as a pedophile:

Epstein had a habit of making light of his reputational and legal troubles. Here he is sharing a news article about himself with tax attorney Erika Kellerhals, telling her not to lose her sense of humor after she expresses sympathy for him:

While in the middle of an unrelated conversation with Ruemmler, Epstein took a moment to crack a joke about his interest in girls:

In another instance, Epstein emailed Ruemmler to compliment a black dress she wore, before he seized an opportunity to make a little joke about sexism:

Epstein saved some of his best riffs for his brother, Mark. The only thing missing from this thread is several implied cry-laughing emojis:

Peggy Siegal, a longtime Hollywood publicist whose career blew up due to her friendship with Epstein, was another frequent correspondent. She twice reached out to Epstein after being inspired to share a travel-inspired racist joke:

Epstein associate Ghislaine Maxwell, who is currently serving a 20-year prison sentence for conspiring with him to sexually abuse minors, had similar qualms about traveling abroad:

Jonathan Farkas, a department store heir who sought romantic advice from Epstein, also popped into Epstein's inbox to engage in some heavy experimentation with punctuation, which got Epstein all fired up about "fals accusations":

Epstein's associates loved to forward to him entire copy-and-paste news articles, although this possibly is a more widely prevalent boomer behavior. Tom Pritzker, billionaire heir and accused sexual abuser, forwarded to Epstein some snarky 2013 Washington Post copy about his cousin, Penny Pritzker, whose nomination for commerce secretary that year was briefly wobbled by the revelation that she'd underreported her income by a whopping $80 million. Penny asserted that it was a simple accounting error, easily corrected; Tom, meanwhile, told his buddy Jeffrey a different version of events:

Epstein's email exchanges with his friends were not always free of tension. See if you can detect any passive-aggressiveness throughout this attempt to wrangle dinner plans with Soon-Yi Previn, Woody Allen's wife:

Epstein maintained a lively email correspondence with his defense attorney, Reid Weingarten. Weingarten appears to have felt comfortable pushing back at Epstein's displays of expertise, where other Epstein pen pals often come across as ingratiating and obsequious. Here Epstein misses the forest for the trees in his criticisms of a 2018 New York Times feature about Donald Trump's inherited wealth:

A personal closeness between Epstein and Weingarten is detectable in the coarse frankness of their exchanges, which extends beyond even the stream-of-consciousness gobbledygook Epstein sometimes unleashed on his more prestigious acquaintances:

Another lawyer named David Schoen, who represented Donald Trump during his second impeachment trial, reached out to Epstein a few times to express his dismay at how Epstein's case was being treated by the press:

As far as we can tell, Maxwell is the only correspondent who ever attempted satire:

No word on whether or not Maxwell also submitted this to The Onion.