In 2019, Bloomberg conducted an investigation into how Epstein, the infamous New York financier, became “island-owning rich.” Their findings, while inconclusive, make it clear that much of Epstein’s wealth — if you can call it his wealth — was given to him by Les Wexner, the co-founder of Bed, Bath & Beyond and longtime steward of Victoria’s Secret.

Tucked away at the end of the report is this fun aside: “Did Epstein win the Powerball lottery while he was in prison?” Okay, now you have my attention.

Hilarious. Epstein is one lucky fella pic.twitter.com/79nOGC2Iis

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— Owen Benjamin (@OwenBenjamin) July 27, 2025

According to Bloomberg, in August 2008, shortly after Epstein began a 13-month prison sentence, an entity named Zorro Trust submitted a winning lottery ticket in Oklahoma for $85 million. Coincidentally, Epstein held a trust named Zorro Trust, which he used to donate money to New Mexico politicians, where he had a ranch called Zorro Ranch.

Sounds fishy, right?

Well, not so fast. The Oklahoman did some digging and discovered that the Zorro Trust, which claimed the winning ticket, wasn’t Epstein’s Zorro Trust, but was instead owned by an anonymous woman who lived across the street from where the winning lottery ticket was sold and who, coincidentally, chose the same name for her trust as Epstein.

So no, Epstein didn’t win the Powerball, but he did win the “become best friends with a billionaire lottery.”