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‘Lolita,’ Jeffrey Epstein, and the Real Meaning of a Challenging Classic
Lolita (1962), based on the novel by Vladimir Nabokov. (Prod DB © Seven Arts production)
How a novel about a pedophile-rapist came to occupy such a prominent place in American life.
By Shilo Brooks
02.19.26 — Old School with Shilo Brooks
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One particular novel is all over the Epstein files: Vladimir Nabokov’s “Lolita.”

Among the more than three million files related to Jeffrey Epstein that were released three weeks ago are scores of references to the book. “Lolita” pops up in emails and in photos, released by the House Committee on Oversight, that show young women with quotes from the book written on their bodies.

Reportedly, this was the one and only book Epstein kept at his bedside table. He owned a first edition. He was a massive fan of Nabokov. And, of course, his plane was famously nicknamed the “Lolita Express.”

“Lolita” is a book about a 37-year-old man who kidnaps and serially rapes a 12-year-old girl. There has long been a fascination with “Lolita” in American pop culture. The illicit relationship it depicts is often glamorized in film, music, and art.

Today, Rafaela Siewert interviews Shilo Brooks about “Lolita”—and how a novel about a homicidal pedophile rapist came to occupy such a prominent place in American life. You can watch the full episode below or listen on Apple, Spotify, or wherever you get your podcasts.

‘Lolita,’ Jeffrey Epstein, and the Real Meaning of a Challenging Classic
‘Lolita,’ Jeffrey Epstein, and the Real Meaning of a Challenging Classic
Shilo Brooks
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The following has been edited for length and clarity.

Why is Humbert Humbert such a compelling character?

Rafaela Siewert: There are moments where Humbert Humbert refers to himself as a pervert. He has some degree of self-awareness. Does the book ask the reader to humanize this man, even though he’s a predator? How do you understand Nabokov’s intent here?

Shilo Brooks: Part of the genius of Nabokov as a writer is that you do come to sympathize with Humbert Humbert in a bizarre way. And it makes you feel uncomfortable because you start to see his point of view, even though it is clear from the very beginning that this book will be told from the perspective of an insane person. Nabokov is interested in exploring, like any great artist, the full range of human psychic possibility in all of its goodness and all of its evil.

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Shilo Brooks
Shilo Brooks is President and CEO of the George W. Bush Presidential Center, Professor of Practice in the Department of Political Science at SMU, and host of the podcast Old School. Winner of Princeton University’s Phi Beta Kappa teaching award, he has also taught at the University of Virginia, the University of Colorado, and Bowdoin College.
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Jeffrey Epstein
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