Top 5 Craziest Prop Bets In Poker History

Top 5 Craziest Prop Bets In Poker History

When risking thousands of dollars at the tables just isn't enough...

Here’s a secret about poker players: They love to gamble.  Shocking, I know.  ‘Prop bets’ are side bets made by poker players in order to spice up the action. The most typical type of prop bet is the ‘last longer bet’ in which two players wager about which one of them will last longer in a specific tournament.  There is also the standard ‘red/black’ for those late nights at the cash game tables where players simply wager on whether the flop will have more red cards or black cards.  However, when high stakes pros want to make things really interesting, they get a bit more creative.  Here are my picks for the top 5 craziest prop bets of all time:

5.) Vanessa Selbst Makes A Drunken Mistake

(Mercier talks about prop bets around the 2:00 mark)

At the 2016 PCA in the Bahamas, a drunk Vanessa Selbst decided it was a good idea to risk $2 million against Jason Mercier’s $10,000 on the stipulation that he couldn’t win 3 bracelets at this year’s World Series of Poker.  It is rumored that Selbst tried to buy her way out of the bet when she sobered up, but Mercier declined.  While no player has ever won 3 bracelets, risking $2 million on such a bet is quite foolish.  Selbst got the scare of a lifetime when Mercier miraculously won 2 bracelets in the first 5 events of the WSOP! He was actually multi-tabling live tournaments, running back and forth between the tables! In the end, Mercier fell short of the third bracelet but managed to win his $2 million the old-fashioned way… at the tables.

4.) Phil Ivey Goes Vegetarian

Back in the height of the ‘Full Tilt’ days when guys like Tom Dwan, Phil Ivey, Gus Hansen etc. were throwing seven-figure sums of money around like confetti, some crazy prop bets took place.  Ivey, a noted carnivore, was challenged by Dwan to go a year without eating meat.  Ivey accepted the challenge and wanted to bet $5 million that he could do it! Dwan agreed to bet $1 million and Ivey went vegetarian…for 10 days.  After less than two weeks, Ivey approached Dwan and agreed to buy-out of the bet for a smaller figure, conceding defeat and probably heading straight to In-N-Out Burger.

3.) Antonio Disqualified For Peeing At The Poker Table

Huh? What? Let me explain.

At the 2016 PCA Antonio Esfandiari was feeling a bit overweight and his buddy Bill Perkins decided to give him a stronger incentive to start exercising (Perkins loves prop bets, you’ll see his name again on this list).  Perkins bet him $50,000 that he couldn’t lunge everywhere he went for 2 days, instead of walking.  After winning the bet Esfandiari’s legs were so sore that he couldn’t physically get up from the poker table.  Due to his inability to walk, Esfandiari urinated into a bottle under the table during the Main Event! He was immediately disqualified from the tournament and made a public apology for the incident.  He won the $50,000 but expressed great regret about his behavior and donated the money to charity.

2.) The King Plays The Most Massive Session In Online History

No list of prop bets would be complete without the ‘King of Prop Bets’ himself, Joe Ingram (AKA Chicago Joey).  Ingram recently won another prop bet by writing an entire 40,000 word book in under a month.  However, his most amazing prop bet achievement came in 2009 when he won a $30,000 wager that he couldn’t play 50,000 hands of online poker in one day.  He accomplished the seemingly impossible feat in just over 20 hours, after playing on 24 tables non-stop during that stretch! Another stipulation of the bet was that he had to turn a profit during the session, which he did easily, winning over $800.

1.) Dan Bilzerian Bikes From Vegas To Los Angeles

Say what you want about instagram celebrity Dan Bilzerian, but he gets the top spot on this list for essentially risking his life to win a bet.   Las Vegas and Los Angeles are separated by 270 miles of hot and unforgiving dessert.  Against all common sense and self-preservation instincts, Bilzerian accepted a challenge to bike between the two cities within 48 hours. Millionaire businessman and high stakes poker regular Bill Perkins (see? the man loves prop bets) bet Bilzerian $600k that he couldn’t do it. Bilzerian trained for 3 weeks and even received some help from Lance Armstrong before accomplishing the feat. There was an interesting side bet to this bet as Rick Salomon (star of Paris Hilton’s sex tape and high stakes poker enthusiast) bet Bilzerian $250k that he would die on the journey. If Bilzerian didn’t die, Salomon would pay him the money. If he died, Bilzerian would leave Salomon his private jet in his will. Fortunately for lovers of Instagram photos of weapons and boobs, Bilzerian survived the journey and won the bet. However, it’s rumored that Salomon has refused to pay his share, declaring that Bilzerian cheated by drafting behind a van for the final stretch.


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