(Before we start, quick definition: Prop bet = "side" bet in which you bet on the outcome of a random outcome or event)
Poker players are famous for their prop bets. As a poker player myself, I love to partake in this tradition. And while yes, I do enjoy to gamble a bit, the fun for me really comes from the fact that mathematical edges can be found in prop bets. For instance, let's say we are at the ball game and we bet on whether or not a guy is going to get a hit in his next at bat... of course one has to factor in his batting average and other statistics to made a prediction. Am I right every time? Of course not, but I enjoy calculating those odds and have found myself on the "good" side of prop bets more often than not! :) Alas, enough about me as my biggest prop bets ever relative pennies compared to the prop bets I'm going to share now...
Prop Bet #1 - While I was playing in that $1,500 Omaha tourney a few weeks ago at the table with Phil Ivey, I was a first-hand witness to the incredible world that pro poker players live in. Just as I sat down, a poker pro from another table (Tony G) walks up to our table to talk to pro player David Benyamine. Both Tony and David were very, very low in chips in this tournament. So low that they'd likely be "all-in" within the next few minutes. Anyway, Tony was like "David, let's make a little last longer bet (the player who lasts longer in the tourney wins the bet)..." (By little, I'd have guessed $50-$100 or so...enough to pay for dinner should they go hang out). Anyway, David was like sure, let's make it 10 (and when these guys say "10", it isn't $10... they are saying $10,000!!). As audacious as this bet is, it is even more silly as these guys clearly will be "all-in" very, very soon and essentially will be flipping a coin to stay alive... results of the bet to come after Prop Bet #2...
Prop Bet #2 - So of course I'm still at a table with one of the highest stakes poker players in the world, Mr. Phil Ivey (see picture above). Phil, never one to let an opportunity to gamble pass him by, instantly said "I want in on that bet... I'll bet on David against you!!" when Tony G and David made their deal. Remember, this "bet" that they are making amounts to no more than a "coin-flip" of sorts as both players will be all-in very soon with any decent hand. Tony is like... okay, another 10? Phil says "nah, 10 is borning, let's go for 50" (yes, $50,000... on a coin-flip... geez!). Anyway, about five minutes later, David Benyamine is all-in with a decent hand and is about 50-50 to stay alive... the cards come out, brick, brick, brick for David and he is bust. Bam! Just like that, Ivey losses $50k... I was watching Phil the whole time and he didn't even flinch one bit. I suppose when you make $5-$10 million/year playing poker, $50k isn't much... but still... so nuts!
Prop Bet #3 - Last July, Phil made a $200,000 prop bet with Daniel Negreanu. The terms of the bet were this: Daniel had until the start of this year's WSOP to shoot an 80 (from the men's tees at a specific course in Vegas). At the time of the bet, Daniel's best round ever was around 88, so he had a lot of work to do. Anyway, one would think that for $200k, both players would have really nailed down the terms of the agreement, but therein lies the controversy, which was the talk of the day at my table... Anyway, back to the golf before we get to the controversy. During August and September, Daniel worked really hard on his game and managed to shoot an 84. However, he hardly played one bit from October to March (remember, $200k is on the line...jeez!). Come April, Daniel realizes that he has less than two months to shoot an 80. His first round back out after his hiatus... a 110...then a 105... then a 98... but nowhere near 80! He gets it down to the low 90's again, but is feeling quite hopeless. All of a sudden, he happens to cross paths with (arguably) the world's greatest golf teacher, Tiger Woods' coach until a few months ago, one Hank Haney... what luck!! In 15 minutes, Hank shows Daniel this little trick and just like that, Daniel adds 20 yards to his tee shots. What a nice little gift. Pretty soon, Daniel is back out to the course every day... shooting 86... 85... getting closer and closer. Yet, this year-long bet is now down to just 2 days!! Here comes the controversy. Having never established all of the rules, Daniel finds it acceptable to "re-start" his round whenever he sees fit. So if he starts off +4 through 5, he just runs back to #1 and starts again. In essence, he just plays the first few holes until he is off to a really hot start. Then he only has to worry about playing well over the final 14 or so. Ultimately, Daniel does this enough and finally breaks through to shoot an 80. Anyway, the hot topic of the day was this: "Did Daniel break any rules?" I'd argue that he didn't...especially since they never set the rules, but ethically? A bit murky... oh well. The funniest thing about the deal is Phil didn't seem to care at all!! It was mainly everyone else at the table discussing the $200k... when someone asked Phil what he thought about it... he just shrugged... "just 200k, no biggie..." Oh, must be nice!
Prop Bet #4 - So I eventually get moved from another table from Phil and find myself sitting down in the midst of another "hot" conversation regarding a prop bet. This one is between two other pros, Mike Matusow and Ted Forrest. Their bet is even more irrational. Mike has bet $50,000 and given Ted 20-1 odds (meaning Ted has to risk losing $50k to win 20 x $50k... which is $1,000,000) that Ted can't weigh 135 pounds by July 17th. Ted currently is 6' 1" and weights about 180, but had accepted the challenge. Anyway, Mike was literally running up and down the tables in excitement over his bet as he viewed it as a "can't lose" bet. But Mike, what if you DO lose.... $1,000,000 is a lot of money!!! Just nuts... completely nuts...
Prop Bet #5 - The biggest bet of the WSOP this year (quite naturally) starts and ends with Tom Dwan. With the mainstream public, Tom definitely isn't as famous as a Phil Ivey or Doyle Brunson, but within the poker community, he is an absolute legend... and he's only 23!! Dwan is perhaps the perfect stereotype of an internet player. Young, super aggressive, eager to bluff, and (more often than not), really, really good! And in Tom's case, good doesn't capture it...he's incredible. It isn't too uncommon for Dwan to be online playing 4-6 tables all at once... with at least $200-$500k in front of him at each table. While I have no exact stats, I wouldn't be surprised if Dwan has won $15M from online poker in the last 4 years (which includes an infamous $6M downswing last November). Anyway, being primarily a cash game/internet guy, Dwan decided to make a prop bet that would generate a lot of action. If offered 3-1 odds (i.e. I could win $100 from Dwan if he didn't win, but if he did win, I'd have to pay him $300), he was willing to bet any amount of money that he'd win a WSOP bracelet this year. Winning a bracelet is tough...even if you play in every single event... this is a fantastically difficult task even that there are many thousands of players. Anyway, no exact numbers have been revealed, but it is speculated that Dwan has $3,000,000 of his own money on the line for this bet (meaning if he wins a bracelet, he will win 3x that amount... some $9,000,000!!!). So, Dwan will either lose $3M or win $9M... a $12M swing. Geez! The big drama occurred in Even #10, when Dwan entered the final 9 of a 2,500 player tournament in 1st in chips! A few hours later, he found himself down to the final 2 (heads up with a complete unknown from New Zealand) with a real strong chance to win this outlandish bet! Anyway, the atmosphere was amazing as every big time pro (many of whom had bet against Dwan and stood to lose a lot of $$) was in the stands to watch the final action. And such an epic (and weird) scenario. This unknown guy (Simon Watt) is probably nervous as all get out... he's playing for about $150k (the difference between 1st and 2nd). Meanwhile, Dwan probably looking cool and calm as ever, is playing for that same difference in prize money... plus another $12M swing if he wins/losses. So sick! Well, about an hour later, in a David v. Goliath type finish, little old Simon Watt became one of the most popular players amongst the big-time pros as he outlasted Dwan for the win!
Bonus Prop Bet - During that same tourney in which I was with Ivey, I also sat with David Sklansky. David is known in the poker community as a "math guru". He's even written a dozen books or so focusing on the math behind poker. All very good reads, by the way. Anyway, he had an interesting prop bet idea: Which is more likely to happen: A pitcher throwing back-to-back no-hitters or someone breaking Joe DiMaggio's 56 game hitting streak? I'm offering a small prize to the person who emails me with the most compelling answer! Of course I'll be looking for some statistics to back up your belief! (by the way, I've done a bit of research on this one myself and I have an idea...but by no means am I convinced that I have this one right)
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