How successful was Andy McElroy at illegal bookmaking? Let’s put it this way—he traveled via private jets and cruised on Johnny Carson’s former yacht. That’s how successful. Then, in 2013, the feds dismantled his $5 billion online sports betting empire.
After his conviction and three years of probation, McElroy left the illegal bookmaking world behind. But his love for high-stakes gambling never faded. Instead, he transitioned to making a living through personal, high-stakes wagers.
“Double or Nothing,” a new documentary now available on Amazon Prime and Apple TV, chronicles McElroy’s riskiest bet yet.
Check out the trailer on YouTube. (Unfortunately, we can’t embed it here due to age restrictions.)
A Million-Dollar Gamble
The story kicks off in 2022, when McElroy proposes an audacious bet to his best friend, G-Man: “I’ll bet you $1 million that you can’t quit drugs and alcohol.”
Against all odds, G-Man accepts. He quits booze, Xanax, and cocaine cold turkey until year’s end—exactly as stipulated.
Though McElroy’s fortune was once vast enough to cover a $1 million payout on a lost 2016 presidential election bet—he was convinced Trump wouldn’t win—by 2022, that amount represented a significant portion of his dwindling wealth. As a fellow Xanax user, McElroy was convinced G-Man would fail.
Oops.
With a million dollars on the line, McElroy scrambles for redemption. He proposes a new wager: if he can complete the Honolulu Marathon in under 10 hours, they go double or nothing.
G-Man accepts. After all, McElroy is 85 pounds overweight and hasn’t walked a mile since 2005.
The Documentary Takes Shape
Enter John Leake. Now a true crime author, Leake grew up across the street from McElroy and witnessed his gambling exploits firsthand. When Leake heard about the marathon bet from his brother Michael, who lives in Hawaii and has connections to professional surf videographers, an idea sparked.
Leake co-directed Double or Nothing alongside Jace Panebianco, known for Broken Molds (2021) and Who is J.O.B. (2012).
A Shady History and Twists Unfold
As the documentary unfolds, new layers of McElroy’s character emerge. In high school, he allegedly paid a gifted student to impersonate him for the SATs. His history of deception raises questions—could he be scheming again?
Tensions rise when suspicions emerge that McElroy may have bribed the film crew to fabricate footage of him completing the marathon.
“To me, this story about gambling and running a marathon is a metaphor for life,” Leake said. “Life is just a series of gambles, trying to beat the odds that stack higher against us as we grow older.”
Double or Nothing offers a raw, unpredictable look at one man’s lifelong addiction to risk—and the unpredictable consequences that come with it. Now streaming on Amazon Prime and Apple TV.
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