Amazon Prime Premieres Unique Indie Gambling Documentary

Posted on: March 13, 2025, 04:21h. 

Last updated on: March 13, 2025, 06:44h.

Corey Levitan Read More

Expertise: Commercial Gaming, Entertainment, Expert Insight, Las Vegas, Restaurants, Las Vegas Myths.

• Illegal bookie Andrew McElroy had his $5B sports betting empire shut down by feds in 2013
• A decade later, he gambled in a big way again
• A new documentary chronicles his most insane bet yet

How successful was Andy McElroy at illegal bookmaking? Dude traveled via private jets and Johnny Carson’s former yacht, that’s how successful. Then feds busted his $5 billion online sports betting ring in 2013.

After that, the Dallas resident — who was convicted and sentenced to three years probation — went straight, but couldn’t stop his degenerate gambling. He switched to earning his income via high-stakes personal wagers.

“Double or Nothing,” a film just released on Amazon Prime and Apple TV, chronicles the aging high roller’s biggest bet.

Check out the trailer on YouTube. (We can’t embed it here because it’s age-restricted.)

The action begins in 2022, when McElroy tells his best friend, G-Man: “I’ll bet you $1 million dollars you can’t quit drugs and alcohol.”

G-Man takes the bet and — to everyone’s surprise — quits booze, Xanax and cocaine cold turkey until the end of that year, as specified.

Though McElroy’s fortune was still big enough to pay G-Man $1 million for his lost bet on the 2016 presidential election — he thought there was no way Trump could pull it off — by 2022, $1 million was the better part of his remaining net worth. A fellow Xanax user, McElroy proposed the bet because he felt certain G-Man couldn’t quit it.

Oops

On the hook for a mil, McElroy offers to complete the Honolulu Marathon, in under 10 hours, for double or nothing. G-Man takes the bet because McElroy is 85 pounds overweight and hasn’t walked a single mile since 2005.

That’s where John Leake enters the picture. Now a true crime author, he grew up across the street from McElroy and witnessed his rise to gambling infamy. Leake heard about McElroy’s latest wager from his younger brother Michael, who lives in Hawaii and hangs with surfing photographers and videographers.

Leake asked his brother to assemble a film crew and capture McElroy’s marathon challenge.

“We did this on a lark,” Leake 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 co-directed “Double or Nothing” with his friend Jace Panebianco, who helmed 2021’s “Broken Molds” and produced 2012’s “Who is J.O.B.”

Switching the Shoe

The plot thickens when it is revealed that McElroy has a history of cheating and getting away with it. In high school, according to Leake, “he paid a really smart guy in our neighborhood to pretend to be him and take the SAT.”

“So there’s this man of different faces and shifting identities that becomes a part of the film,” Leake said.

Conflict erupts between Leake and his brother when suspicion arises that McElroy may have paid off the crew to film him fraudulently completing the marathon.

“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.