Jeffrey Epstein and I are very different. Obviously, there’s the “Ep.” But also the pedophilia, the arrest record, the islands, the private jet, and the three Amazon orders in 2017 of herbal vaginal tightening pills, which is the kind of subtle hint that I have never been able to pull off through gifting.
I know about the Vagifirm purchases because Epstein is the first person whose online purchases and email correspondence are public, thanks to the Epstein Files Transparency Act. Which meant that, if I had the stomach for it, I could discover how different Epstein’s life was from mine – and, by proxy, all decent, upstanding people. So I asked Gemini, Google’s AI, to search through 23 years of my Gmail and compare them to the 23 years we have of Epstein’s. The first thing I learned was that this is a bad idea. There are a lot of emails I sent that I forgot ever sending. I also forgot what was acceptable to say 23 years ago. Some of those things became not okay, and then okay again. But some of it is still not. And I said those things. Epstein and I have emailed with at least nine of the same people, one of whom is Charlie Rose. I mention Rose to lessen the shock of the next one: Harvey Weinstein. None of my emails with Weinstein were sexual. I was merely asking him to let me fill out his Oscar ballot, as part of my plan to control two votes and make outrageous demands of the studios as the most powerful person in Hollywood. Though I don’t know what would have happened if Weinstein had asked me what I was going to give him in return for his vote. As someone who never makes crude jokes about rape, I was surprised at how often I make rude jokes about rape. Even on threads that included my lovely wife, Cassandra. I also emailed a friend about Cassandra’s refusal to have a second child, in which I came up with a workaround: “Cassandra has an IUD. I’d need to roofie her, call in an OBGYN to remove it, and finish before she woke up. Doable.” Possibly. But definitely prosecutable. While I have interviewed Amy Adams, I do not have a thing for her. Which makes it even more strange that I agreed to Skype into the class of a famous scholar by saying, “Especially if we talk about Amy Adams’ breasts. I even wanted to see her boobs in Her. And The Muppets.” When an actress I interviewed complained to me that a photographer the magazine assigned to shoot her was so creepy she referred to him as “Cosby,” I did not do anything about it. But the really damning part was how much Epstein-like slimy ladder climbing I’ve done. I arranged an Epstein-esque dinner at my house so Reza Aslan could meet the writer Michael Green, after David Brooks slagged them both in the same column. I am constantly kissing up to the elite: Sending Judd Apatow an email after liking a stand-up joke of his, or Steven Pinker after he quoted me in a speech, or you about how Steven Pinker quoted me in a speech. Worse, Gemini noted, “A striking mundane overlap: you have threads about finding an internship for your son, Laszlo. Epstein’s files are filled with him leveraging his network to place the children of billionaires and academics into elite positions.” The only thing that made me feel good about as far as my career as a journalist goes is that Gemini is still so bad at writing that it thinks that the phrase “striking mundane overlap” makes sense. I learned two important things from this exercise. One: I’m gross. Not as gross as someone who buys a $102.64 lace wedding dress and $13.98 veil from Amazon for reasons I can’t even guess at. But I don’t clear that bar by much.
Two: We shouldn’t make anyone’s digital life public, no matter how corrupt they are and how much we don’t trust the federal government to prosecute them. Our digital communications are complex webs. No one should know about my wife’s awful rape jokes. We all say regrettable things all the time, though probably not as much as Epstein or I do. Still, the assumption of privacy is a prerequisite for intimacy. Normal, healthy, emotional, adult intimacy. Sometimes, our intimacy is with people who do bad things. And we should protect all the decent people who have ever emailed me. Thank you for paying to read my column. Wait: This is for the people who didn’t pay? Then I owe you nothing. You are the ones contributing to the end of my career. If you want to pay an exorbitant amount of money to get one extra post a month – which often won’t even be that good – upgrade to a paid subscription here:
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Friday, March 27, 2026
The Stein Files
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