High rollers: How prop bets are taking over the lives of the World’s best poker players

In today’s poker world, tales of insane prop bets and huge losses on sports are as common as stories about the game itself

It sounds like an urban legend. You know, the gambling version of those sketchy stories about people getting themselves dosed with sedatives, having a kidney removed, then waking up in a bath full of ice.

Our questionable tale concerns John ‘Johnny World’ Hennigan, the chrome-domed pool hustler-turned-poker pro who is well known for playing the highest cash games and keeping a low media profile. It goes like this: Hennigan got his hands on a million dollars cash at the Bellagio poker room and, after the game broke up, proceeded to the blackjack pit where he began playing every spot at one of the top-limit tables.

When a fellow poker pro walked by and asked Hennigan what the hell he was doing, Hennigan replied, ‘I’m going to keep playing until I lose this money.’

Not surprisingly, the story concludes, Hennigan accomplished his mission.

On the side of believability, there is the fact that Hennigan is not afraid to gamble. He once bet $30,000 that he could live in Iowa for 30 days (his hope was that he’d be bored enough to focus on his golf game, but he wound up settling). But that blackjack story? It sounds beyond the pale and way too public a display for a guy as private as Hennigan. Did it really go down like that? He acknowledges that it did. Then he shakes his head with concern. ‘People think these stories are funny,’ says Hennigan. ‘But to me it all seems kind of sick.’

Got the fever

Maybe so. But one thing for sure is that John Hennigan is hardly alone. In fact, he is in exceedingly good company. For better or worse, many of the world’s greatest poker players also happen to be among the world’s most reckless gamblers when it comes to “Many of the world’s greatest poker players also happen to be among the most reckless gamblers” games they can’t consistently beat.

Some players claim there’s a method to the madness. For example, when Sammy Farha leaves the poker table to play blackjack for five-figure sums per hand, it’s about blowing off steam from the Big Game.

Others don’t even bother to make excuses. They just can’t help themselves. Ram Vaswani acknowledges, ‘When I watch a game I have to have money on it.’ He won’t give specific figures, though Vaswani does allow that small money for him is ‘a few thousand and big is a few hundred thousand’. And Mike Matusow pretty much starts the football season with an expectation of dropping six figures to Las Vegas bookies – any less would be a win.

Then there are the wagers that get made in the midst of poker but have nothing to do with a game of skill. Barry Greenstein maintains that when the highest stakes players engage in prop bets at the table – purely luck- based wagers on combinations of cards that will come on the flop, turn and river – they are doing it as a way of remaining focused while out of hands.

Vaswani, hardly a prude when it comes to pure gambling, views it differently: ‘It’s entertaining to see stuff like that. But I don’t think it’s productive. I remember playing in an Omaha tournament and watching Phil Ivey and Doyle Brunson prop betting for more than the first prize in the tournament. It gets a bit ridiculous. I don’t know how you’re meant to focus on a tournament when you’re gambling for more than the prize money.’

Live to bet

It’s been said that many of the highest stakes poker players are pathological gamblers who are fortunate enough to have found a productive, skill-based outlet through which to channel their compulsions. Indeed, what’s won in the poker room is all too often blown in the pit. Phil Ivey is notoriously high- rolling when it comes to craps, as is lovable UK pro Willie Tann.

Ted Forrest has acknowledged, in these very pages, that the only time he’s ever dropped $1m was at the craps table rather than the poker table. Roland de Wolfe has trouble leaving a stint of blackjack, and one of the best-known European players has managed to go broke through an infatuation with, of all things, high stakes slot machines (a trap for de Wolfe as well). Gavin Smith laughs about losing $30,000 at Nintendo Wii Sports bowling, and this year you can count on Erick Lindgren and Daniel Negreanu to each have half-a-million dollars at stake on fantasy football.

So what’s going on here? ‘There is the theory of the arousal element; they may get off on taking chances,’ says Dr Paul Rogers, senior lecturer in the Department of Psychology at University of Central Lancashire, offering a serious bit of unintentional understatement. ‘Or they may be driven by a belief that they can overcome the odds. They may understand the difficulty of winning. But they are getting a buzz out of it.

There may be an illusion of control. It’s like people who think they can influence the outcome of dice by rolling them in a certain way.’

Realistically though, who can expect professional gamblers not to gamble? It’s what they do for a living and it’s what they do for fun. ‘I’ll gamble on anything,’ says Vaswani. ‘I remember being at one particular tournament and a guy there said what he was going to pay for his plane ticket to go to the next tournament. I didn’t believe he could get the ticket that cheaply. We bet $500, I won, and it turned out to be more money than the ticket itself would cost.’

On a more serious level, he remembers a golf wager he made, back when Tiger Woods was still an up-and-coming. Vaswani got odds of 16/1 on him winning the Masters. ‘I thought it was a price I’d never see again, so I made the bet and he won his first Masters. I won about $50,000. It was a great bet and a great price.’

Right now, the big gambling trend among young poker studs is betting on their own golf games rather than those of the PGA stars. The most audacious of these has come from Erik Sagstrom, who’s courted action to the tune of $10m to $100m that he’ll make it to the US Open within the next 10 years. Lindgren and Ivey have a $500,000 bet, spread over 10 years and centering around Ivey’s ability to beat Lindgren in 72 holes of match play. And it’s been said that Negreanu has dropped a million dollars to Doyle Brunson.

For a lot of poker pros, the drag of gambling away from the game they play best goes beyond the financial downside. Roland de Wolfe marvels at the hours he’s wasted in the pit. Vaswani acknowledges that non- poker gambling has ‘gotten me in trouble a million times’.

According to Josh Arieh, the question is this: ‘Are you going to let the gambling control your life? Or are you going to control the gambling? If you let the gambling wash over into everything else, you’re in trouble.’

The starkest example of a player allowing gambling to taint his poker, of course, is Stu Ungar. During Ungar’s latter, most degenerate years, an out-of- control drug habit conspired with runaway sports betting to destroy anything he accomplished at the poker table. ‘He went through so much money that he always had his neck on the blade,’ says veteran pro gambler Billy Baxter. ‘He needed to win every day just to support his bad habits. Then he’d lose a couple of days in a row and go bust.’

Gotta give action to get action

Despite that worst-case scenario, a compelling argument can be made that gambling big not only goes hand-in- hand with poker, but that it actually helps things along. Certainly it’s good for one’s table image.

If you have a reputation as a bloke who likes to give action – Antonio Esfandiari, for example, tells me that he and Phil Laak once bet on the type of panties a girl would be wearing and that he routinely does over/under bets on dinner tabs (loser pays) – it is only natural that you’ll get action on the felt.

‘People call me when they won’t call others because they know I’m capable of making big bluffs,’ says Vaswani. ‘I remember a tournament a few years ago when I got all my money in with Aces and a guy called me with a really weak hand. He called me because he thought I would go in with anything.’

Being known as a gambler has paid off for Marc Goodwin as well, but he acknowledges that it comes at a price. ‘Gambling big seems to be a need,’ says Goodwin. ‘It’s a sickness. We’re all gamblers and most of us have leaks in our games. All the big players punt sports really big; $100k a game is nothing. Phil Ivey, Ram, Gus [Hansen], myself – we all do it and we’re the biggest going. Our punting is higher than our poker.’

I find this to be a little strange and ask Goodwin why it’s the case. He ponders the query for a beat, then replies, ‘There has to be a certain amount of pain involved. If it doesn’t hurt me to lose the money, then I won’t bother.’

The hurt, though, goes beyond the immediate win or loss. Confirming what Arieh says, Goodwin acknowledges that it’s virtually impossible for non-poker gambling to have no impact on your poker game. Lose money away from the table and you’re liable to be chasing. Cash in with the bookies and, well, I’ll let him tell it: ‘You become overly confident and overly aggressive. I’ve had days when I’ve won $200,000 sports betting and called off 15 grand that I wouldn’t have normally called off. I did it because I had the extra money.’

When it comes to non-poker gaming, Goodwin bets sports and golf, enters into prop bets at the table and enjoys famously silly bets, but he saves his biggest wagers for bouts of spread betting.

‘I put a bet on runs scored at £50 per run in the cricket and got on the right side of things in a big way. I bought two South African batsmen and they ended up scoring 279 and 179 respectively, giving me a return of 375 times my per run stake of £50! That’s a win of about £18,000. I had no idea that would happen – I honestly thought I was going to win or lose a couple of thousand at the most.’

Out of control

Though things worked out perfectly that time, Goodwin acknowledges that it’s not the norm: ‘The problem there is that it made me feel invincible, and I’m not a winning sports bettor. As I found out about $165,000 later.’

It’s the same story for Roland de Wolfe, who has dropped loads to the bookies and just about every other outlet for action.

‘I don’t know how much I’ve lost and I wouldn’t like to work it out,’ he admits. ‘So many times I’ve played brilliant poker all week and built up money. Then I’ve stopped by the pit and literally lost it all. You go in telling yourself you’ll lose $2,000 and leave. Then you wind up losing 50 times that. Self-discipline and control go right out of the window.’

Vaswani agrees: ‘I’ll gamble on anything in the pit. It’s ridiculous and should only be for fun, but you get bored and want excitement. It’s tough to avoid in Vegas. Then I’ll lose money and look to play a tournament to get out of trouble.’ This, he acknowledges can cut both ways. ‘Sometimes you play the tournament less well. Or else you concentrate better than you normally would because you really want to get your money back.’

Like Vaswani, de Wolfe is well aware of the pitfalls that come with playing games you can’t statistically beat. ‘If I do it high enough, I will lose all my money,’ he admits, adding that he’s working hard to rein in his non-poker play. ‘I didn’t play any pit games between December and June. But I lapsed during the World Series. I played roulette and baccarat and Pai Gow and dice and blackjack and, uhm, slots.’

What’s your poison?

He considers all of this, then figures that the economy of scale between the pit and the poker table is part of the problem. As a fellow poker player once told de Wolfe, ‘Betting at sports [or in the pit] is bad for a poker player because it makes your wins and losses at poker seem irrelevant. If you’re playing $20,000 a hand at blackjack, it’s easier to win and lose large sums of money.’ And, partly for that reason, he says, ‘It’s poison for poker players. It’s like a drug and it ruins poker players’ lives.’

Therein lies the conundrum. What do you do when a love of competition, a love of games, a passion for high stakes risk have all worked in synch to get you to the top of the poker heap? If you’re like most poker players you accept the good with the bad, you keep gambling, and you make the best of what is inarguably, for many, an occupational hazard.

Not everybody can be Chris Ferguson or Andy Bloch, so strongly focused on mathematics that gambling lacks lustre. But not everybody needs to be a Stu Ungar either, blowing their brains out with impossible wagers. And, in fact, most players do manage to find that sticky middle ground where they gleefully bet $20,000 on being able to eat salad for a week but stop short of putting a million bucks on a roster of Nflgames they barely understand.

Seeking clarity on this matter, I defer to the simple logic of the ever-wise Howard ‘The Professor’ Lederer (who lost $10,000 on a standing backflip bet with Huck Seed, but did manage to win $35,000 through a no-smoking bet with nicotine addict Hennigan): ‘When you’re a gambler, you back up your beliefs with a bet. That is what you do.’

And maybe, in the end, that reasoning is so sound that it should liberate all of us to enjoy a bit of extra action away from the poker felt.


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