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Introducing the 2018 Gambling Olympics: A $30,000 Betting Free-For-All

Introducing the 2018 Gambling Olympics: A $30,000 Betting Free-For-All article feature image
  • The inaugural Gambling Olympics takes place in Las Vegas on July 9-10.
  • The event features 12 of the gambling world's biggest names competing as individuals and teams in 12 separate events.
  • The $30,000 prize pool will be awarded to the individual first-, second- and third-place finishers and the highest-scoring team.

If you listen to “The Three Donkeys” podcast, you know that Jonathan Bales, Peter Jennings and Adam Levitan like to gamble. They’ll bet on almost anything, from games of racquetball to what each other is thinking.

With that passion, they’ve created the world’s first Gambling Olympics.

The two-day event pits 12 like-minded individuals against each other in a series of gambling events. The festivities informally begin with a number of preliminary prop bets before the main event kicks off in Las Vegas on Monday, July 9.


Before, during and after the Gambling Olympics, we will provide extensive coverage via participant profiles, event breakdowns and live in-person analysis. Within this article we will link to content as it’s published, so bookmark this piece to follow all the action!

Matthew Freedman’s Live Analysis & Daily Recap

In its infinite wisdom, The Action Network has assigned Matthew Freedman to cover the Gambling Olympics in its entirety in person so he can provide live analysis and recap the events of each day. Be sure to follow all the high-stakes tomfoolery.


The Gambling Olympics features a who’s who of industry personalities (listed alphabetically):


The field has been divided into three teams captained by the Donkeys:

Buy-In & Prizes

The buy-in is $2,500, yielding a total pot of $30,000, most of which will be awarded to the top quarter of the field:

  • First Place: $10,000
  • Second Place: $6,000
  • Third Place: $4,000

The final $10,000 will be divided among the members of the winning team.


Before the main event, several participants will engage in a series of prop bets, some of which are already scheduled and more of which will undoubtedly arise from the moment. These props include:

A couple of these props have particular rules we should elucidate here.

Pullup Prop

  • Bales -17 pullups vs. Jennings
  • Bales must use wide grip, and Jennings can use neutral grip
  • Pullups to be graded by Levitan

Tennis Prop

  • Adams vs. Levitan
  • Adams cannot lose a game in two sets; must win 6-0, 6-0
  • Match to be played at Cosmopolitan
  • Players call their own lines (in/out)

Main Event

The Gambling Olympics consists of 12 separate events, which run the gamut of the speculation spectrum:

Side Action

Although the buy-in for the Main Event is $2,500, a majority of the big action will be in side bets.

Main-Event Rules

In each event, every participant will be ranked first through 12th and receive the inverse number of points:

  • First receives 12 points
  • Second receives 11 points
  • Etc.

The final individual standings will be based on cumulative points in all 12 events. The standings for each team — for both single events and the entire Gambling Olympics — will be based on the total individual points for the entire team. Tiebreakers for both individuals and teams will be most events won.

Crypto Portfolio

  • $1000 to spend, must select a minimum of three coins on Binance
  • Use price on Binance as of 10 a.m. on Monday as open and Tuesday 6 p.m. as close
  • Cannot change portfolio
  • Final standings based on profit/loss

Daily Fantasy Sports

  • DraftKings MLB lineups selected on Monday and Tuesday
  • DraftKings WNBA lineup selected on Tuesday
  • Final standings based on cumulative score from all three contests

Sports Betting

  • $1000 to spend, must bet at least three games (spread or moneyline) on Monday and Tuesday
  • Can place between $1 and $998 on each game
  • Everyone uses same lines
  • Final standings based on profit/loss after two days


  • No-Limit Hold ‘Em tournaments on Monday and Tuesday
  • Two six-handed tables until six remain, then one table
  • Final standings based on average finish after two days


  • $1000 to start, can bet any amount each hand
  • Standings based on staying in (first person to bust is last)
  • If still in after one hour, rankings based on total money won/lost
  • Final standings based on profit/loss after two days

Beer Pong

  • Bracket style; matchups chosen at random
  • Top two most dominant wins based on cups remaining get bye (tiebreaker for bye is time to win)
  • Rankings for losers based on total cups made
  • Tiebreaker for losers is one-cup throw-off
  • Final standings based on average finish after two days


  • $1000 to start
  • Two groups of six players (randomized to start and then again at 30 minutes)
  • Cannot bet more than you can afford to lose (half of money); no reloads
  • Standings based on staying in (first person to bust is last)
  • If still in after one hour, standings based on total money won/lost


  • Bracket style; matchups chosen at random
  • Byes and standings determined by score

Connect 4

  • Bracket style; matchups chosen at random
  • Best-of-three series
  • Two most dominant wins get bye (fewest pieces used to win)
  • Final standings for losers based on pieces used


  • Bracket style; matchups chosen at random
  • Best of 21 head-to-head matchups
  • Top two in fewest losses after first round get bye in second round
  • Rankings for losers based on total throws won
  • Tiebreaker is best of seven among all tied parties
  • Final standings based on average finish after two days

Lodden Thinks

  • Everyone answers two questions as accurately as they can before the competition
  • Scott the Intern will come up with the questions, and no one will know them ahead of time
  • Sheet handed out with 22 questions listed (the questions asked to the other entrants)
  • Example: How many black holes does Peter think exist in the universe?
  • Get score of 1 to 11 on each question based on how close a guess is compared to others
  • Final standings based on highest total score
  • Tiebreaker is most questions won

Standings Prediction

  • Predict the final standings, first through 12th, by Monday morning
  • Points are awarded for inaccuracy (if a guess is 12th and the person wins, that is 11 points)
  • Fewest points wins
  • Tiebreaker is best guess on winner


In the event a contestant cannot compete in the Gambling Olympics for any reason — such as still being in the World Series of Poker Main Event — he will be assigned a replacement. All standings and bets/prizes for the teams will be calculated as normal with the replacement filling in. All bets on the absent individuals will be void.

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