Download the App Image

2018 Gambling Olympics: Jennings Has the Heart to Win $3,000 Racquetball Bet vs. Bales

2018 Gambling Olympics: Jennings Has the Heart to Win $3,000 Racquetball Bet vs. Bales article feature image

The Highlights

  • Before the official Gambling Olympics, some of the participants will compete against each other in preliminary events.
  • One of these events is a series of racquetball matches between Jonathan Bales and Peter Jennings.
  • Jennings has verified toughness on the racquetball court.

The 2018 Gambling Olympics is a two-day, 12-person contest taking place in Las Vegas on July 9-10. The buy-in is $2,500, and the winner gets $10,000.

Before, during and after the Gambling Olympics, we will provide extensive coverage via participant profiles, event breakdowns and live in-person analysis. Be sure to follow all the action in the Gambling Olympics section of the site.


Racquetball: Bales vs. Jennings

The Three Donkeys have long been proponents of bets centered around physical fitness, and whenever they are together, they like to engage each other in competitive sports. A few days before the Gambling Olympics, Jonathan Bales and Peter Jennings will compete against each other in a multifaceted racquetball prop that will have at least $3,000 riding on it.

It also wouldn’t be surprising if at some point Adam Levitan got in on the action both as an athlete and speculator. It wouldn’t be the first time for these three degenerates to duke it out on the racquetball court.

The Layered Racquetball Prop

Almost all of the details for this prop were worked out during a 40-minute negotiation between Bales and Jennings, who are also competing against each other in a $2,000 pull-up prop.

If Jennings wins the pull-up competition, he then gets to wager $1,200 against Bales at even money that he can shut out Bales in the first game of their racquetball match. If Bales wins the pull-up competition, then the shutout prop is reduced to $1,000 so that Bales has less risk.

Additionally, Bales and Jennings are wagering $2,000 on the total match, which will have three sets (15 points in the first two, 11 in the third). For first serve, they will have a best-of-seven Rock-Paper-Scissors contest.

In exchange for taking this presumably disadvantageous prop, Bales gets the benefit of facing Jennings later in a best-of-101 Rock-Paper-Scissors contest with $2,000 at stake. Although Bales is giving Peter +110 odds, Bales is confident in his skills. After all, he’s a massive +175 favorite in a 12-person field to win Rock-Paper-Scissors in the Gambling Olympics.

Can Bales Beat Pete?

Jennings is almost certainly better than Bales if he’s betting that he can shut out Bales in the first game. Levitan favors Jennings in the upcoming matchup: “I’m slightly better than Bales, and last time I saw him, Peter was a decent bit better than me.”

Of course, in the famous racquetball match from February of 2017, Levitan quickly “defeated” Jennings by TKO with the help of a wall, so he knows what he’s talking about.

Came to FLA for a friendly game of racquetball. Ended up in an urgent care wait room because @CSURAM88 was going way too hard, ate a wall.

— Adam Levitan (@adamlevitan) February 19, 2017

As Bales’ primary racquetball competition and training partner in Philadelphia, Levitan has valuable firsthand experience, but it’s also possible that he’s too close to the situation and has too fraught of a relationship with Bales to be objective. Their on-court rivalry is storied. Levitan claims that Bales has quit playing against him to write a new MLB book, while Bales maintains that Levitan stopped playing so he could trade “little fake internet coins.”


What is Jennings going up against? In the words of Bales, the poor man’s version of Kane Waselenchuk.

@CSURAM88 @adamlevitan Who do you guys model your racquetball game after? Mine is Kane Waselenchuk. Power player. Leaves it all on the court

— Jonathan Bales (@BalesFootball) January 20, 2017

Waselenchuk finished the 2016-17 season as the No. 1 player on the International Racquetball Tour for the 12th time, so it’s safe to say Bales means business, but what does that really mean?

Although Bales has the strength advantage, racquetball is a game built on determination and grit. It’s tough to back an athlete who isn’t willing to run through a wall to get a win. Pete has no problem with running into walls.

Shutout pick: Jennings
Match pick: Jennings

How would you rate this article?