Jeffrey Epstein Won a $29 Million Powerball Jackpot the Day After Entering Prison — Coincidence or Cover-Up?

The Epstein rabbit hole just got deeper. For a man linked to presidents, princes, spies, and what may be the biggest blackmail network in American history, you’d think the shock factor had maxed out.

But now, a jaw-dropping detail has resurfaced: a $29 million Powerball jackpot mysteriously won the day after Epstein entered jail in 2008—following a bizarre computer glitch and a secretive, closed-door lottery draw.

According to The Daily Oklahoman on August 26, 2008, “a financial planning company based in Oklahoma City received $29.3 million Monday on behalf of the Zorro Trust, which held the winning ticket from the July 2 drawing.”

The winner remained cloaked behind legal layers, with lottery officials acknowledging the use of a trust to shield the identity. “We were hopeful that they would come in, but as time passed, we know they were going to form a trust,” said Jim Finks, an official quoted in the article.

Then, out of nowhere, Zorro Trust claimed the jackpot. At first glance, just another wealthy individual opting for privacy. But the timing is hard to ignore: on July 1st, 2008—just one day prior to the draw—Jeffrey Epstein began serving his 18-month sentence in Florida as inmate W35755.

Is it possible Epstein received $29.3 million via a shell trust while behind bars?

That possibility becomes harder to dismiss when looking at the history of Zorro Trust. In the Albuquerque Journal dated September 4, 1994, Zorro Trust is explicitly linked to Epstein: “Zorro Trust is headed by Jeffrey Epstein of New York City,” the article stated, quoting a source named King, who said Epstein “planned to form Zorro Ranch.” Though Epstein couldn’t be reached for comment at the time, his involvement with Zorro Ranch in New Mexico is well-documented.

A listing in the New Mexico Environment Department’s Ground Water Quality Bureau names Brice M. Gordon as both the ranch manager and the manager of Zorro Trust, listing his contact as [email protected]. Gordon also appears as a principal of Zorro Development Corporation, a private New York-based management company. Its staff? A mere two people. Even Epstein’s “black book” includes a New Mexico entry for Zorro Ranch, listing a number associated with Brice and Karen Gordon.

The ties between Epstein and Zorro Trust are not speculative—they’re public record. Which is why the question remains disturbingly valid: Did Epstein, through the Zorro Trust, collect nearly $30 million from the Oklahoma Powerball while sitting in a Florida jail cell? And is it coincidence that Epstein’s pilot, Larry Visoski, in his deposition, is asked directly:

Mr. Edwards: The Zorro Trust winning an 85 million dollar—claiming the ticket for 85 million dollar Powerball ticket in 2008.

https://twitter.com/kelly2277/status/914599884027777026?s=20

Why mention this at all—unless there’s more to the story?

Jeffrey Epstein and Bill Clinton’s financial ties

Adding to the bizarre financial web surrounding Epstein are his past dealings with the U.S. government. On December 23, 1997, The Daily News reported that a “small castle” at 34 East 69th Street in Manhattan had been leased to Jeffrey Epstein by none other than the U.S. State Department, starting in 1992 at a monthly rent of $15,000.

The lease was managed through the Office of Foreign Missions (OFM), whose job is to serve foreign diplomatic personnel and ensure compliance with diplomatic privileges and immunities. So why was this arm of the U.S. government renting a property to Epstein, a private citizen and financier?

A phone log from April 19, 1996, records Epstein speaking with OFM to extend the lease—originally agreed to run from February 1992 through January 1994. It was later extended to 1997. The lease explicitly limited occupancy to Epstein, his family, and approved guests. According to court records from a 1996–1998 federal eviction case, Richard C. Massey, an OFM official, was Epstein’s point of contact.

In an uncanny timeline twist, Epstein had made a political donation to Bill Clinton on January 30, 1992. Just two days later, he moved into his luxurious East 69th Street townhouse, secured via the State Department’s Office of Foreign Missions. Another coincidence? Or something deeper?

Epstein’s murky fortune has long been the subject of speculation, particularly in connection with Ponzi schemes. His mentor, Steven Hoffenberg, pleaded guilty in 1995 to orchestrating what was then the largest Ponzi scheme in U.S. history, defrauding investors of $460 million. Hoffenberg, who later sued Epstein (and then dropped the case), maintained that Epstein was a key architect of the fraud: “He was great at moving money illegally,” Hoffenberg told Vanity Fair. “He was the deeper architect to getting things accomplished.”

And the pattern didn’t stop there. Epstein was also named in connection with the $1.4 billion Ponzi case involving Rothstein Rosenfeldt Adler. Everywhere a Ponzi scheme turned up, Epstein seemed only one degree removed.

“You’re about to see an entire story about this supposed billionaire and the story about his financial empire, which is as big as the tragedy with the girls,” Hoffenberg said. “It’s billions of dollars, and it’s a fiasco.”

So what are we to make of the Zorro Trust Powerball winnings in July 2008? A shadowy trust with documented ties to Epstein wins a glitch-riddled, untelevised lottery the day after Epstein is incarcerated. Coincidence, or cover-up?

As always with Epstein, the deeper you dig, the darker it gets—and the more questions emerge that those in power refuse to answer.

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