Double or Nothing: Wild Wager Turned into Amazon Documentary

Andy McElroy wasn’t just another bookmaker – he was a legend in the underground sports betting world. 

His success was measured in private jet flights and time spent aboard Johnny Carson’s former yacht. That is, until the federal government took down his $5 billion online betting empire in 2013.

Following his conviction and a light sentence of three years probation, the Dallas resident tried to turn over a new leaf. 

Double or Nothing

McElroy’s love for high-stakes gambling never faded. Instead of running illegal sportsbooks, he shifted his focus to placing massive personal bets.

His latest wager is the focus of “Double or Nothing,” a documentary now available on Amazon Prime and Apple TV.

The story kicks off in 2022 when McElroy challenges his closest friend, G-Man, with a life-altering proposition: “I’ll bet you $1 million dollars you can’t quit drugs and alcohol.”

To everyone’s shock, G-Man accepts. He ditches alcohol, Xanax, and cocaine on the spot and stays clean for the rest of the year, just as the bet required.

Despite having once been wealthy enough to casually lose a seven-figure bet on the 2016 presidential election—he was convinced Trump would never win—McElroy’s financial situation had changed. 

By 2022, $1 million represented a significant portion of his remaining fortune. Believing G-Man could never follow through, McElroy found himself on the losing end of the wager.

Faced with the reality of paying up, McElroy proposed a double-or-nothing alternative: if he could complete the Honolulu Marathon in under 10 hours, the bet would be wiped clean.

G-Man agreed, confident his friend, who was 85 pounds overweight and hadn’t exercised in years, stood no chance.

“We Did This On a Lark”

The plot thickened when true crime writer John Leake, who had grown up witnessing McElroy’s gambling exploits firsthand, entered the stage. 

John’s brother Michael, a Hawaii resident with connections in the surf photography world, heard about the bet and told John about it. 

The latter suggested they should document the unfolding drama by assembling a film crew and capturing the marathon challenge. 

“We did this on a lark,” he told Casino.org. “But when we reviewed the footage and the dialog, we saw it was just so funny and so cinéma vérité, we just said, ‘Let’s make a documentary out of this thing.’”

Leake partnered with filmmaker Jace Panebianco, known for “Broken Molds” (2021) and “Who is J.O.B.” (2012), to co-direct the project.

As the story unfolds, viewers learn that McElroy has a long history of bending the rules. In high school, Leake recalls, “he paid a really smart guy in our neighborhood to pretend to be him and take the SAT.”

The Story, “A Metaphor for Life”

This theme of deception took center stage when rumors started swirling that McElroy may have bribed the film crew to stage his marathon finish. 

Tensions rose as Leake and his brother clashed over the integrity of the footage. 

“The plot thickens as Andy appears to cheat. At stake are $2 million and a 30-year friendship,” the Amazon Prime description reads.

“To me, this story about gambling and running a marathon is a metaphor for life, which I think of as a series of gambles to beat the odds that stack ever more against us as we grow older,” Leake said.

The documentary delivers more than just a high-stakes bet. It’s a deep dive into the mind of a compulsive gambler, the blurred lines between truth and illusion, and the lengths some will go to escape the consequences of their own actions.