A chilling personal ritual of Jeffrey Epstein's has surfaced in the latest installment of Michael Wolff's ongoing diary series.In a post published Monday on hisA chilling personal ritual of Jeffrey Epstein's has surfaced in the latest installment of Michael Wolff's ongoing diary series.In a post published Monday on his

Epstein's chilling and frequent private question revealed in new report

2026/07/06 23:52
2 min read
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A chilling personal ritual of Jeffrey Epstein's has surfaced in the latest installment of Michael Wolff's ongoing diary series.

In a post published Monday on his HOWL Substack, Wolff centers the 16th chapter of The Epstein Diaries on a question the accused sex trafficker reportedly asked aloud with unsettling regularity: "Am I having fun?"

Epstein's chilling and frequent private question revealed in new report

The phrase was rhetorical, Wolff wrote.

"Obviously, a man who had everything he could possibly want and access to everyone he wanted to know was having fun. But in another obvious sense, he was always taking stock, measuring the risks of an unchecked life (existential, as it turned out) against the rewards of getting all he believed he wanted," wrote Wolff.

Wolff claimed the question served a dark function, giving Epstein a pretext to inventory his pleasures — ticking through his travel itinerary, the high-powered figures he was meeting, and the sweeping world problems he entertained as intellectual diversions.

"It was, too, a knock on everyone else's seriousness," Wolff said. "Epstein had achieved a personal remove which made life an amusing spectacle."

Wolff said Epstein's question raised one of his own.

"But it was also weirdly open-ended and certainly prompted the question: 'Was he having fun?'

Epstein was found dead in his cell at the Metropolitan Correctional Center in Manhattan on Aug. 10, 2019, while awaiting trial on federal sex trafficking charges. New York City's chief medical examiner ruled the death a suicide by hanging, a finding his lawyers publicly disputed.

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