Breaking Down the Man Behind the 2,400-Pushup Prop Bet: Who Is Jonathan Bales?


Pictured: Jonathan Bales

Who is Jonathan Bales?

I did a quick radio hit this morning with 96.9 The Game in Orlando, and I was asked that question as the lead-in to a conversation about the $2,000 pushup contest that has caught the attention of Gambling Twitter.

For those who don’t know him, here’s a quick introduction to Bales.

Who Is Jonathan Bales?

Jonathan Bales is the Co-Founder of FantasyLabs, which is part of The Action Network.

So he’s an entrepreneur. A risk taker.

He’s also the author of the “Fantasy Sports for Smart People” series.

So he’s a writer. A thinker.

And according to his personal blog, he’s a couch potato.

That’s true to a degree.

But he’s also a physical specimen. In 2018, he crushed 31 pullups in the Gambling Olympics preliminary events without breaking a sweat while legitimately hungover.

He’s astoundingly competitive. He absolutely hates to lose. One of the top moments of the Gambling Olympics was when Bales lost at Rock-Paper-Scissors and then seriously fumed about it for 15 minutes.

Of course, Bales still won the Gambling Olympics anyway. When it’s something that he cares about, he rarely loses. The dude is a winner.

On top of that — and Bales will never admit this — he’s almost certainly a sandbagger. More than once I’ve heard him say something like, “I’m just not sure about this” right before he annihilates a prop bet.

And Bales is something of a paradox. He has a wondrously bizarre combination of humility and confidence. If you peruse his Gambling Olympics profile, you’ll see this statement: “My strongest event will be Rock-Paper-Scissors. Everyone knows I’m one of the world’s greats.”

What a ridiculous thing to say.

How much hubris must a guy have to think that he could possibly be one of the best in the world at anything, especially something as random as Rock-Paper-Scissors?

And yet Bales somehow might actually be the best RPS player on the planet — and he has the humility to say “one of the world’s greats” instead of “the world’s greatest.”

Simply put, Bales is truly one of a kind.

And by the end of Thursday, April 2, I expect that he will be a dude who just did 2,400 pushups in 12 hours and won a lot of people a lot of money.

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