Prop betting is the new past time of the super high stakes poker player. Should we be surprised? “It has nothing to do with the money, insists Daniel Negreanu”

For some of the high stakes poker pros, winning (and losing) hundreds of thousands of dollars playing cards isn’t enough…

High stakes online poker pro Steve ‘stevesbets’ Jacobs was close to broke. But he had $ 2,000 sitting in escrow, securing a crackpot prop bet that most of us would make only if we really didn’t care about the money. Jacobs cared deeply, but he also believed that he could win the bet: drink 10 disposable cups of soda and identify each one as Coke or Pepsi. ‘I’ve drunk Coke and Pepsi for a long time, and I can tell the difference,’ he says. ‘I was getting two-to-one odds, betting against Andrew Robl and our friend Luke Kim [both of whom are online poker pros]. Luke asked me if, after eight or nine cups, I thought I would still be able to tell the difference. I replied, “Would you be able to tell the difference between drinking soap and drinking water?”’

Forty minutes later, after taking three sips from each cup in order to confirm and reconfirm his taste buds, Jacobs was no longer broke. He had the winnings – $ 6,000, including the $ 2,000 that had been held in escrow – deposited directly into his PokerStars account.

Taking advantage of the fresh ammo, Jacobs immediately began playing $ 75/$ 150 Omaha Hi-Lo. Within two hours, he ran his bankroll up to $ 25,000, and so began what he now describes as ‘the biggest heater of my life’. The prop bet proceeds set him on a rush that got as high as $800,000 and was at about $ 400,000 when he finally decided to take a break. More recently, Jacobs snagged first place in the WCOOP $ 25,000 heads-up event on Stars. He took down $ 560,000, though some of that windfall went to backers.


Few people run meagre prop bet winnings up to $800,000, and fewer still risk their last bit of money on a wager that seems, at best, goofy. Nevertheless, prop betting clearly has its place in the high stakes poker world, and it seems to be bigger than ever. During a poker tournament at the Atlantis resort in the Caribbean, Tom ‘durrrr’ Dwan paid a fellow poker pro $ 5,000 for risking his life in the resort’s shark tank; within minutes, though, the payoff was blown to Mike Matusow in a single hand online.

More recently, durrrr squared off at chess against an online player who happens to be a world class player at the game. Dwan figured that a rook headstart would give him an insurmountable edge. Six figures later, he discovered that he was wrong. Durrr’s buddy Robl paid $25,000 to a guy who spent a month living in the bathroom of a Bellagio hotel room, and a rakish friend of theirs recently talked about betting that he could have sex with a different woman on each of five nights per week for an entire year. ‘And they’ll all be sevens or better,’ informs the guy who has requested anonymity. ‘With all the tourists coming through town, Vegas is the perfect place to do it.’

Another pro, who’s also asked to remain anonymous, supposedly took home half a million dollars by winning free-throw and three-pointer bets during this past World Series of Poker. During the same Series, Mike Matusow famously snagged $ 100,000 in a weight-loss bet with Ted Forrest, and Phil Ivey dropped seven figures when he failed to make good on a series of wagers that had him needing to win a 2008 WSOP tournament. Maybe feeling that there wasn’t enough pressure or inducement to take the preliminary events seriously, Ivey made a parallel bet with Daniel Negreanu: first player to take down a gold bracelet receives $ 200,000.

Then there was the third-party wager that Negreanu was unwittingly involved with. ‘Doyle Brunson made a bet that me and Lee Watkinson and Lee Markholt [combined] will win more bracelets than Phil Ivey and Allen Cunningham [combined],’ recounts Negreanu. ‘Doyle made that bet in the VIP room of the World Series, which is where a ton of random bets get made.’

Brunson and Negreanu both benefited when Kid Poker finished first in the $2,000 Limit Hold’em event.


What drives normally cool-headed poker pros to make these kinds of wagers for sums that would equal a good year’s salary for the rest of us? ‘It has nothing to do with the money,’ insists Negreanu. ‘It’s more about keeping score – and if the points are too small, then it just isn’t any fun. Beyond that, of course, we’re all sick, degenerate gamblers. We enjoy the action.’ Offering an example of the action, he recounts a bet made at the poker table with Ted Forrest: ‘I was 138 pounds at the time and laid him 20/1 odds that I would never weigh 170 pounds in my life. He gave me the money up front and the next day I became a vegetarian.’

While Negreanu enjoys playing $ 2,000 nassaus on Golden Tee, he and the other pros really kick up their wagering – prop betting and otherwise – when it comes to tests of physicality, with golf reigning as a day-to-day favourite. Though afternoons of 18-hole action do not come close to generating the sums that are won and lost each night at the poker tables, golf bets are still plenty astronomical.

Patrik Antonius has had many six-figure swings on the course, including one time in which he and his assistant/ golfing partner Nick Rainey dropped a tidy sum to Daniel Negreanu and Negreanu’s caddy. But it hasn’t dampened Antonius’s enthusiasm for this type of gambling: he’s planning to play tennis against Gus Hansen for $ 200,000. ‘Gus is pretty tough,’ admits Antonius. ‘Gus was top three in Denmark among under 20-year-olds. We practised together last year and he would have beaten me that day.’

David Benyamine
has been training for a tennis match of his own – versus a Russian poker pro, for $ 500,000, slated to take place sometime during the 2009 World Series – and, by the time this article goes to press, he will have squared off against Phil Ivey. ‘Phil and I have a $ 400,000 bet, straight up, one round of golf,’ says Benyamine, acknowledging that he definitely did not have the best of it back when the match was first made. ‘It seemed crazy to a lot of people, but I trust the guys who are helping me with my golf game. They see big potential and encouraged me to take the bet.’

Erick Lindgren – about whom it’s been stated that the poker table is the only place where he doesn’t gamble – has made all manner of goofy bets, ranging from foul shooting contests to fantasy football (a couple of seasons ago his wagers stretched up toward the mid six figures) to a golf prop that had him needing to walk a desert course on a hot summer day, carry his clubs, play four rounds and break 100 on each round. Lindgren did it, took down $ 300,000, and described the experience as ‘excruciating and retarded’.

Maybe so, but that bet of Lindgren’s is far from the silliest one that he’s made. Advised via telephone that his friend Gavin Smith was trying to raise money to wager on whether or not a wealthy California-based gambler could leap from an automobile roof to a hotel awning, Lindgren impulsively took a piece of the action. That turned into a quick 85-grand for the hard-gambling poker pro.

Back at the tables, Patrik Antonius remembers a night in Bobby’s Room when he got involved with high stakes prop betting (wagering that certain cards would hit the board over the course of dealing out hands). ‘I lost $ 640,000 in one day on props,’ he grimly recalls. ‘I don’t even want to think about it.’ Chip tossing at the Aussie Millions – betting on who could land a chip closest to the wall – wasn’t exactly profitable either. At $ 10,000 a toss, he dropped $ 40k.

Heads or tails?

Regardless of your take on chip tossing as an intellectual pursuit, however, it’s hard to argue against Negreanu and Ivey as the twin kings of frivolous gambling, based solely on this anecdote: ‘Phil and I were at the Sacramento vs San Antonio basketball game,’ recalls Negreanu. ‘We had floor seats, and a coin landed underneath my foot. We bet $ 10,000 on whether it was heads or tails.’ After that initial wager, things escalated: ‘I’d place the coin under my foot and Phil would have to guess what it was. We did that 11 times.’ Acknowledging that he has little recollection as to who actually won the series of bets, Negreanu adds, ‘It got stupid and we finally went back to watching the game.’

While it is generally difficult to view most prop bets as anything more than a way to blow off steam and have high stakes fun, there is another component. At their best, props allow poker pros to develop fresh disciplines, get good at things they might not ordinarily have it in them to pursue, and actually improve their lives. It’s driven Antonius and Ivey to ratchet up their golf games, led Huck Seed to learn how to do a standing back-flip, and transformed old-school prop king Amarillo Slim into a crack marksman with a bow and arrow.

A positive benefit was in the air when Matusow shook hands with Ted Forrest and embarked on his $ 100,000 weight-loss wager. In pursuit of the 100 grand, Matusow needed to lose 60 pounds, going from an unhealthy 241 to a downright svelte 181 between the end of the 2007 World Series and the start of 2008’s. He did it, and literally transformed his appearance. All the more amazing is the fact that Matusow and his girlfriend embarked on a full- frills cruise just as his day of reckoning was nigh. Matusow gained seven pounds while at sea and managed to drop the requisite 15 during the final nine days of his timeframe. He won the money and turned heads at the WSOP.

Soon after his opponent made weight – with the help of a master cleanse and long sessions in the Jacuzzi – Forrest presented Matusow with another potentially profitable opportunity: Matusow would have to keep his weight below 185 for an extended period of time. Soon after the proposition was offered, Matusow called me with an update on his dieting. ‘I’ve gained back 11 pounds this week,’ he practically bragged. ‘Right now I’m eating a 20-piece Chicken McNugget meal. And guess what? It’s gooood!’ Needless to say, Part II of the weight-loss bet is one prop that never came off – at least for the time being.

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