Lolita and Epstein's emails

In the podcast, I looked how elections last week revealed some ways it’s possible for candidates to reject the current trans panic, stand up for everyone, and win. You can watch the episode on YouTube or listen to it via Apple, Spotify, and elsewhere. If you’d like to check out the linked material or the written post from Tuesday, you can read it here.

A quick heads-up on next week: I’ll be in Roanoke, where I went a year ago in December and again in March to see how the residents of a blue dot in a very red Congressional district were reacting to Trump’s victory. In the wake of last week’s big wins for Democrats, I’ll head back to look at how they spent that year and what they’re doing next. So the Tuesday post will drop on Wednesday next week, with some fun highlights.

If you have a pulse and are currently living in the United States, you’ve probably heard something or other in recent days about Jeffrey Epstein’s emails. One of the most horrific aspects of what’s been revealed so far about the exploitation has been the degree to which all kinds of rich people and those in positions of power praised Epstein, deferring to him and helping him with a wink or a nod years after he’d pleaded guilty on state charges of solicitation of prostitution with a minor.

It’s possible to argue that he did his time on those charges, and that, unless they had special knowledge of what else he had done, people had no strong obligation to shun him after his release. But today I want to address one aspect of the disturbing ways in which powerful people treated him after his conviction, the way his notoriety seems to have been almost an asset. Rather than take on the thousands and thousands of emails as a whole, I want to focus on the 29 references to Lolita in the emails.

I know more about the novel Lolita than any person probably needs to, because of the book I wrote over a decade ago on Vladimir Nabokov. For those who haven’t read Nabokov’s novel or seen the movie versions of Lolita, the book recounts a middle-aged man’s sexual obsession with a girl. As the plot progresses, the narrator Humbert Humbert meets Lolita, becomes her stepfather, and ultimately kidnaps her, going on a cross-country trip in order to more easily molest her. His crime spree goes largely unobserved, with one key exception. Unfortunately, Clare Quilty—the person who recognizes what the narrator is doing—is just as much of a monster.

In terms of the emails that dropped this week, the 29 references to Lolita shed light on how those around Epstein made it possible for him to do the things he did. There’s a lot of repetition, as replies bounce back and forth and include chunks of prior text.

Winnowed down, the Lolita mentions in the records reduce to three specific items, each of which points to a different way Epstein was enabled by public figures.

The Lolita Express

In several cases, emails contain copy-pastes of news stories referencing the unofficial nickname for Epstein’s private plane: the “Lolita Express.” The nickname indicates a kind of truth in advertising that should have led some people to ask more questions.

It’s not clear from these emails how many people had heard the phrase when dealing with Epstein. But he himself seems to wink at his proclivities, as when then-former White House Counsel Kathy Ruemmler uses the word “girls” in an innocuous sentence in 2014, and Epstein replies, with his unique punctuation, “girls?”„ careful i will renew an old habit.”

By the beginning of 2015, the “Lolita Express” nickname had become public knowledge and national magazine feature fare. It was known that he had likely transported countless girls by airplane to unsupervised settings for years. Nevertheless, emails after that date reveal that support for Epstein, as well as his collaborations with powerful people and institutions, continued for years after his persistent interest in young girls was understood.

Ever since Lolita’s publication in the 1950s, the name has been tied to both highbrow literary concepts and pornographic innuendo. The latter missed much of what was in the book—Humbert’s acknowledgment of his crimes—or embraced that violence. But the highbrow crowd often missed a lot, too. Even in those circles, “Lolita” was invoked as a wink to the taboo and universal nature of men lusting after young girls.

That the novel was also literature helped that taboo enter a gray area for a lot of adult men (and some women) who saw themselves as sophisticates. Even director Stanley Kubrick seemed to wear blinders, seeing Lolita as “a very sad and tender love story.”

The Harvard professor

Another strange interpretation of the novel shapes the second category of Lolita mentions in the emails. Elisa New, then a literature professor at Harvard University, wrote to Epstein in 2018 for help with inviting celebrities to collaborate on a television project.

It seems they had already discussed Lolita at some point. New says that she will reread the novel soon, and encourages him to pick up Willa Cather’s My Antonia. “The book has,” she writes, “come to think of it-- similar themes to Lolita in that it's about a man whose whole life is stamped forever by his impression of a young girl.”

New is describing a book in which a man sweeps his stepdaughter away from her boarding school and hides the death of her mother in order to rape her, only noting later that she is in physical pain. Elisa New’s gloss is an odd one to put on the text when talking to someone infamous for having a predilection for molesting minors.

It also casts My Antonia in a strange light. In Cather’s book, not only is the narrator a little younger than the girl (and later, the woman) at the heart of his story, but the actual way that novel most resembles Lolita is that at one point, a creepy older man angles to get Antonia alone to rape her.

If all these emails are real, how did this professor end up discussing Lolita with Epstein, a convicted sex offender? Either he brought it up or she did. If he did, she seems not to have skipped a beat in asking him for favors. If she did, it’s even stranger.

In another part of the Epstein emails, New drafts or sends an email to Woody Allen, bringing up “seductive” and “aggressive” readings of the William Carlos Williams poem “This Is Just To Say,” which suggests some broader indulgence or encouragement of wealthy, connected men already infamous for grotesque or illegal behavior.

These emails indicate that a lot of establishment people did exactly the same thing. Their reputations and attention kept Epstein aloft while he managed to skate far above the vast network of abuse he’d committed for years. It’s no small irony that Professor New’s husband, Larry Summers, appears to have asked Epstein for dating advice a year later, though the couple were still married.

The book on the bedstand

The last category of mentions of Lolita in the emails is one in which Epstein or his associates share articles mentioning the book itself. These boil down to one apparent fact: a visitor observed that the only book Epstein had on his bedside nightstand was Lolita.

Some of the emails mentioning this seem to be part of the fact-checking process for a planned 2015 New York Magazine profile about Epstein. The fact-checker is going through the story in draft form and attempting to verify details with Epstein. One of several odd scenes in the piece includes the journalist writing, “The single book on his bedside table is Lolita (he is, beyond the joke, a great Nobokov [sic] fan).”

The reporter in this draft also writes that “Epstein is the Dreyfus of the rich.” (Alfred Dreyfus was hounded into horrific captivity on Devil’s Island as part of a vast conspiracy to stoke antisemitism in France for the benefit of reactionary politicians.) At one point, he describes Epstein as a Peter Pan type, “an insistent playboy (excuse me, pedophile) in a correct and prudish world.”

To be Jeffrey Epstein and have Lolita as the lone book at one’s bedside would be a provocation—and a kind of test. I would argue that the reporter playing this idea as a “joke” might mean he passed the test with Epstein. But as a test of his humanity, he failed. The final line of the article in the email is “Anyway, I hope I get invited back to Jeffrey’s house soon.”

The book itself

For anyone who reads the book cover to cover, the situation is laid out. Humbert himself narrates, “An expression of pain flitted across Lo’s face. It flitted again, more meaningfully, as she settled down beside me... I asked her what was the matter. “Nothing, you brute”... This was an orphan. This was a lone child, an absolute waif, with whom a heavy-limbed, foul-smelling adult had had strenuous intercourse three times that very morning."

But it has to be said that Nabokov also wants it both ways in the novel. He clearly is trying to deliver a narrator who loves literature and is trying to exalt his infatuation with a child into a transcendent love story. Even after Humbert indicts himself, he works to excuse himself. The degree to which you let him persuade you of his love mirrors the degree to which you implicate yourself as a reader.

Nabokov himself had a repetitive fixation on girls molested by an older figure. The theme appears in his work again and again. It repeated across decades to a degree that became unseemly as a person and detrimental to the art he created. In a 2009 essay for the Guardian, Martin Amis ticks through the examples of Nabokov characters’ sexual infatuation with young girls—and he doesn’t even include prior examples that stretch back to much earlier writing from Nabokov.

To be clear, Nabokov does appear to have cavorted to some degree or another with undergraduate students when he taught Russian language classes after emigrating to the U.S. during World War II, when he was in his forties. But unlike Epstein, there’s no suggestion at all from anyone during his life or after his death that he acted out any part of his writings on underage girls.

It’s entirely possible that he himself had some psychic turmoil from his Uncle Ruka about whom he writes in his autobiography Speak, Memory. Recounting the times he sat on his uncle’s lap and was fondled and called sweet names, Nabokov also recalls his father coming into the room and putting a stop to their private conversations.

But Nabokov was also a little bit of an edgelord. He crafted Lolita and other works with the direct intention of shocking polite society. Yet he did so in such a way as to put one over on those who find a way to ignore evil through inattention. He may be scratching his own psychic itch and maybe even winking at readers as they’re taken in by Humbert’s self-serving cruelty. But in the end, he’s mocking them and showing them how complicit they are.

Nabokov isn’t above turning the tables on his readers. As Amis noted, Lolita is “a cruel book about cruelty.”

The book he wrote was shocking enough to be censored in the 1950s. But later, with the rise of Playboy magazine’s cheesy centerfolds that ran back to back with literary articles, the world shrugged, acknowledging that pornography and literary writing were just different ways (as often as not) for men to assert themselves over women as a lifestyle. They could both be used to brush over and even endorse much grimmer realities lived by people you didn’t have to pay attention to. By the early 1970s, an actual child pornography magazine named Lolita arrived in the Netherlands and continued to be published for sixteen years.

All these aspects have blended into the kind of “kidding on the square” mentality about Lolita that edgelords of 2025 are still using on any number of issues. There’s never a shortage of people willing to overlook or abet exploitation of the vulnerable.

Humbert himself offers an explanation in the book for his particular attraction to girls between the ages of nine and fourteen, giving his obsession a quasi-rational and quasi-historical context. So perhaps we shouldn’t be surprised when Megyn Kelly appeared to try to defend Epstein in a similarly convoluted way on Wednesday, drawing distinctions between raping a girl decades younger when she is fifteen versus five.

The star of Kubrick’s Lolita, Sue Lyons, was fourteen years old when she got the role. Nabokov reported being happy with the choice at the time. But later, he saw images of Catherine Demongeot, who starred in Zazie dans le metro and was barely ten when that film came out. In a sign of what he had really been trying to do, Nabokov commented that she, instead of Lyons, would have been the perfect actress to play Lolita.

Seeing what Demongeot looked like in the film is a good reminder that Lolita is meant not just to charm but also to horrify us. There will always be Humbert Humberts and their collaborators who will parse ages and intentions, who will wink at the pain that others inflict, if it gains them an iota of power. And Nabokov was definitely poking fun at conventional morality.

But one level down, he was saving his most savage knifework for those who failed to see their own monstrousness in giving Humbert a pass. Readers might nod and try to seem savvy about modern mores. But near the end of the novel, even Humbert acknowledges the girl who broke down in “sobs in the night—every night, every night—the moment I feigned sleep,” and understands he is a monster.

Your paid subscriptions support my work.