Big Smoke Meets WhiskyFest Is Coming May 28th. Buy Tickets Now.

The Good Life

The Hold'em Hackers

Not content with making a fortune at the tables, poker pros are now taking aim at golf
| By Michael Kaplan | From Richard Branson, Sept/Oct 2007

It was the summer of 2006 when Daniel Negreanu realized that poker's biggest players had completely flipped for golf. Over the course of a few weeks that season, the Bellagio's highest stakes tables remained eerily vacant. Deep-pocketed sharks were going to bed early and rising in time to tee off before it got too hot. "It was kind of creepy," remembers Negreanu, standing in the living room of his Las Vegas home, as he obsessively takes practice swings with a clicking and ratcheting contraption that is designed to perfect his drive. "The golf action had gotten bigger than poker. Everyone who played in the Big Game seemed to be out on the golf course." Indeed, among top poker players, golf has become a Hold'em doppelgänger. There's even a new tournament format, dubbed the World Series of Golf, in which you literally bet on holes as if they're Hold'em hands (not surprisingly, two top poker pros made it to the final foursome). On the cash tip, guys such as Barry Greenstein, Doyle Brunson, Bobby Baldwin, Phil Ivey and Erick Lindgren have all embraced (or, in some cases, reembraced) the game at its highest stakes level. And they're putting their Benjamins where their mouths are. Rounds at Shadow Creek with $50,000 wagers on every hole are not uncommon. Baldwin recently landed a 45-foot putt and collected $120,000 on spontaneous side bets. Lindgren casually dropped $10,000 after goofily wagering that he wouldn't toss a golf club for the remainder of a round. He smirks and acknowledges that he hung in there for 20 minutes.

Swedish pro Erik Sagstrom is so bullish on the game that he's invited wagers as to whether he can make the U.S. Open within 10 years. "I asked him if he would bet $1 million to $10 million," recalls Mike Sexton, commentator for the World Poker Tour. "He said it would have to be $10 million to win $100 million. He knows how hard it is to get that good; he'd need to give up his poker career. But it shows the confidence the guy has and how skillful he thinks he can get." It also shows how big golf has become among gamblers. No doubt, on his way toward the Open, Sagstrom, whether he makes it or not, would become sharp enough to win much more than $10 million by gambling on the course.

The gumption of transplanted Parisian poker star David Benyamine is nearly as audacious as Sagstrom's. After playing the game for just two weeks, he made a sizable bet with Doyle Brunson, wagering that within two more weeks he could outplay Brunson, who had once been close to a scratch golfer but is no longer that adept. Brunson wanted to book the bet, recounts Negreanu, "but people convinced David not to do it. It's actually impossible for him to win, and nobody wants to see the money going to Doyle and leaving the poker economy."

Veteran gamblers such as Brunson, Bobby Baldwin and Dewey Tomko have been playing high-stakes golf for decades. Back in the 1970s, Las Vegas Country Club reigned as the site for seven-figure matches. By the turn of the century, however, as poker was poised to become America's hottest game, action on the course dried up. But now the pendulum is swinging back again. "The new players are gamblers at heart," says Sexton, a fixture at Shadow Creek, where he regularly squares off against Brunson and Baldwin (who rides the course with two bags of clubs). "I like to play for $20,000 a hole [rather than $50,000, which is the preference of Baldwin and Brunson]; that way you're unlikely to lose more than $100,000 in a single day."

Sexton allows this to sink in for a moment before recognizing how outrageous it all sounds. "You have to realize that these guys play in poker games where you can easily drop half a million dollars over the course of a session. So having a $100,000 win or loss at golf just isn't so big. It's difficult for an ordinary guy to understand this, but that's just the way it is."

The point is driven home on a spring morning in Las Vegas. Negreanu and Lindgren embark on a friendly round with fellow poker pros Shawn "Sheiky" Sheikhan and Gavin Smith. The match is being held at Canyon Gate, a private country club, and is being taped by the online site After a 45-minute warm-up on the driving range, punctuated by loads of negotiating, needling and squabbling, a complex skein of bets is stitched up: all told, there will be $19,000 wagered on every hole. Negreanu and Lindgren each book $5,000 total-score bets with Sheikhan (Negreanu needs to break 99, Lindgren needs to break 84), a few Nassaus are thrown into the mix, and they head off to the first tee.

Continually angling to get today's action higher, no doubt convinced that he can stomach mega-stakes better than some of his competitors can, Negreanu grumbles, "We're playing so cheap it's embarrassing." That said, a few holes in, with his potential profits for the day already passing $25,000 and the round shaping up to be one of the best of his life, he doesn't exactly appear to be blushing. But he is a little bummed: "Why can't I be shooting like this when I'm playing against Doyle for $50,000 a hole?"

Among poker pros, it is largely agreed that the recent spate of golf action was kicked off by Texas Hold'em champ Phil Ivey. Once nicknamed the Tiger Woods of Poker, Ivey is now looking to do that moniker justice. By all accounts he took up golf to have something constructive to do when he wasn't playing poker. But as a gambler, Ivey couldn't get motivated by engaging in $100 Nassaus. But once the golf-gambling poker pros realized that Ivey was willing to drive and putt for the same stakes he risked at the Bellagio, they were on him. After all, he was a superstar at the table but a novice in the tee box. His quick infatuation with golf presented a perfect opportunity for them to snatch away some of his Hold'em millions.

For a while Ivey was the live one when it came to matching up (that is, negotiating strokes and terms, which is at the heart of every golf wager). At the beginning he blew a lot of money on the course. But then something happened: Ivey got tired of losing and became serious about the game. He hired a former tour pro known as Danny to coach, caddie and advise on matchups. Ivey reportedly pays Danny a weekly salary and a cut of the winnings. In exchange, says Negreanu, "This guy's always with Phil on the course. Basically, Phil will not play without Danny. Besides helping Phil to match up and improve his game, Danny can detect hustlers from a mile away."

Sometimes, however, bizarre things happen. Negreanu remembers one match between him and Ivey in which Ivey had fallen behind and was having trouble with his swing. In the middle of the round, Ivey pulled out a couple dozen golf balls and turned the fairway into a driving range, working with Danny to straighten out his swing before he'd be willing to continue the match. "I sat there and got iced," recalls Negreanu, "while he hit practice shots. It's not normally allowed, but we're friends and he told me that if he can't hit the ball, he's going to quit for the afternoon." This is something that Ivey is notorious for. He only gambles hole for hole (as opposed to playing Nassaus) and negotiates the provision that he can bail at any time. In that regard, he treats the golf course as if it's a poker table. If he's not feeling up for it, or believes that things are unlikely to fall his way, he leaves—often without even saying good-bye.

When things are going well, however, Ivey has no aversion to making big bets. On a trip to Hawaii, while he and poker pro Joe Cassidy were playing for relatively low stakes ($5,000 a hole), Ivey found himself facing a 60-yard chip shot. As related by Negreanu, Ivey asked Cassidy to bet him on it and got 200-to-1 odds on a $1,000 bet. The correct odds have been placed in the range of 2,000-to-1—so Cassidy was getting a pretty good price—but then Ivey sunk the chip for a $200,000 payday. Cassidy, by all accounts, felt pretty sick about the whole thing.

But not all of Ivey's golf bets are so easy to win. Soon after undertaking golf he made a long-term wager with Erick Lindgren. "Phil and I mouth off to each other all the time, and I told him that he will never beat me in 72 holes of match play," remembers Lindgren. "So we made a half-million-dollar bet on it. He has 10 years, with 10 tries a year, to do it. And we made another bet for this year: the same deal, 10 tries. As far as this year goes, I think he's got no shot. Even Phil makes a bad bet sometimes."

And even when the bet is a perfectly good one, he occasionally has a hard time collecting. Such was the case when Ivey tangled with British poker pro Ram Vaswani and his golf/poker buddy Marc Goodwin during the Aussie Millions poker tournament this past January. Ivey and his caddie slaughtered the Brits. Vaswani and Goodwin cried foul, maintaining that Ivey had misrepresented the degree to which he'd improved since their last match (which Ivey had lost and paid off). The sum that Ivey and his caddie won was well into the six figures and driven up by Vaswani's desire to get even. When the sand cleared, however, he refused to pay. Vaswani's logic for reneging? He had been hustled by a friend.

Soon after that imbroglio, the matter was settled in the way that a lot of gambling disputes are: a three-person arbitration committee convened behind closed doors at the Bellagio. Chip Reese, Erik Sagstrom and Gus Hansen heard all sides of the argument. The situation is supposedly resolved and by mutual agreement the decision has been kept private.

Regardless of how things were hashed out, the very fact that Goodwin and Vaswani would use the hustling allegation to get out of paying speaks volumes about the prevailing attitudes of young golfers today. Back in the day, when poker pros were repeatedly fleecing and getting fleeced, hustling was a part of the game. (Puggy Pearson, for example, once came close to getting shot after he kicked his ball to improve its lie during a big match against the convicted marijuana trafficker Jimmy Chagra, a notorious pigeon in the 1970s.) Russ Hamilton, who won the World Series of Poker in 1994 and is a notoriously tricky golf opponent, once marveled, "Regular golfers don't have it in them to miss a hole on purpose. They always play as well as they possibly can." Not Hamilton. When a hole is inconsequential, he will happily flub it to increase his equity in the match or in the future.

The irony of high-stakes golf among the new-generation players is that none of them are really very good and, thus, not really in a position to hustle. Most of the hackers, Ivey notwithstanding, are admittedly too lazy to improve their games. As a result, they shoot in the 90s, although they gamble with the gusto of scratch players. This has created fabulous opportunities for Mike Sexton, who seems genial as host of World Poker Tour but becomes a killer on the golf course, especially when the money of a young poker pro is at stake. "Sexton can be a dog," maintains Lindgren. "Last year, he said that he can't break 90. Then he went out and shot 77 on me. He won eight bets and $80,000. Hopefully, though, I'll give him his medicine someday. I'd like to punish him."

Back on the greens and fairways of Canyon Gate, the foursome of poker stars squares off against one another amid simmering action. Going into the last three holes, Negreanu has distinguished himself as the big winner for the day. At the moment, he is positioned to go home with $40,000 or $50,000 in profits from what thus far seems like a friendly round of golf.

But like all friends on the course, each of these men manages the game's frustrations differently. Lindgren, who is being spanked to the tune of $30,000, handles his losses with little more than the occasional grimace and groan. Husky Gavin Smith has exercised his propensity for pitching golf balls after blowing easy putts. Sheikhan is playing well enough but sweating every hole on his home course, jumping in and out of bets, getting into an argument with Lindgren about moving a ball away from a sprinkler head (but laughing about it right after) and half-seriously accusing his opponents of sandbagging. Negreanu, meanwhile, is coasting through the round and loving every second of it.

At the same time, however, he never forgets that this is as much about gambling as it is about golf. Illustrating the point, he recounts an incident that took place while he and his friend Lindgren were playing a round in Lake Tahoe. "I hit the green, had a 15-foot putt, and Erick bet me $10,000 to win $20,000 on the putt. I was getting a stroke on the hole, so I pretty much had that bet won," he says. "Now it was all about sinking this putt. His ball was lined up with mine, and he was going first, so I had an opportunity to see which way the green broke. He was about to hit the ball, when he looked at me and said, 'You've got to be kidding.'" Lindgren whacked the ball off to the side, unconcerned about his own score. He was much more interested in keeping his opponent from gleaning any knowledge about the impending putt. The subterfuge, by the way, was for naught: Negreanu made it.

By the final hole today, it actually looks as if relatively small sums will change hands. "If things go well," Lindgren tells me, "I'll owe $40,000 to Negreanu and win $20,000 from Sheiky and Gavin." He smiles widely and adds, "Losing $20,000 at golf? That'll be a beautiful day for me. Just perfect."

He's not kidding. Considering the stakes that he and Negreanu routinely play for, this is pretty much a wash. Maybe that can be chalked up to their knowing each other well enough to make matching up difficult. That's logical. Completely illogical is the gambling bug that suddenly bites Gavin Smith, and becomes downright infectious, on the final hole.

Approaching the 18th tee box, Smith is down $38,000, all told, to Negreanu, Sheikhan and Lindgren. The amount would be cataclysmic to your average golfer who shoots in the high 80s or 90s, but it's perfectly manageable for Smith. Maybe it's too manageable. Maybe that's why he rapidly books another $40,000 in bets, all on this last hole. The wagers set off a feeding frenzy, and Sheikhan takes bites of action from what quickly turns into a smorgasbord of risk—including a $30,000 bet between Lindgren and Negreanu which, when you factor in their Nassau, will result in Lindgren owing his friend $100,000 or $40,000. But it's Smith who's really going to town. He's getting strokes, he's giving strokes, he's the locus of wagers that have the potential to carve out a big winner and a big loser in a round that, just a hole ago, appeared to have the high-stakes equivalent of beer money at risk.

Lindgren comes through on the 18th hole, building off of a long, straight drive to beat Negreanu. They're near the green, sitting in a golf cart, looking up the fairway as Smith tees off on a hole in which he's ultimately booked $60,000 worth of action. From their vantage point, Negreanu and Lindgren see a drive dribble off of the tee. It's followed by another shot, which is difficult to follow but gets punctuated by a club being tossed 30 or so feet in the air.

"He's gonna lose the whole 60," marvels Lindgren.

"He's gonna lose his mind," declares Negreanu.

Then Negreanu turns to me and explains, "Gavin's not used to going off for that kind of a number at golf."

In the end, Smith loses all the bets, save for one that he pushes against Negreanu, who winds up ahead $74,000 on the day. Sheikhan wins $13,000 and Lindgren is up $1,000. The big loser is Smith, who is down $88,000. He looks unhappy but isn't sticking around to gripe. There are no tears, no settling up (that'll happen later, off the course), no 19th-hole cocktail in the clubhouse. With the sun setting in Las Vegas, there's just enough time to head home, shower, change, eat and hit the poker tables, where a long night of Hold' em could really decide who's ahead or behind on the day.

Michael Kaplan is a Cigar Aficionado contributing editor.


More in The Good Life

See all
The Cigar Of The Year Meets The Whisky of the Year

The Cigar Of The Year Meets The Whisky of the Year

The best Cigar of the Year and the most exciting Whisky of the Year will be paired together at the …

May 12, 2022
Cigars for Warriors Celebrates 10 Years

Cigars for Warriors Celebrates 10 Years

Cigars for Warriors (CFW), a nonprofit that ships cigars directly to U.S. troops deployed across the …

Apr 20, 2022
Grant’s Revolvers And More Civil War Items At Auction

Grant’s Revolvers And More Civil War Items At Auction

On May 13, Rock Island Auction Co. is putting up several items of Civil War history on the block, …

Apr 15, 2022
An American Dream

An American Dream

Inna Tuler was broke when she fled war-torn Israel in 1991. Today, she’s the head of a California …

Mar 30, 2022
Sweepstakes Winners Get Their Prize: Full Boxes Of The Cigar Of The Year

Sweepstakes Winners Get Their Prize: Full Boxes Of The Cigar Of The Year

Our annual sweepstakes has ended and three lucky smokers have each won a box of Padrón 1964 Anniversa…

Mar 25, 2022
Limited Edition Hine Cigar Cognac On Sale In United Kingdom

Limited Edition Hine Cigar Cognac On Sale In United Kingdom

Hine Cigar Reserve, a cognac specifically made to pair with fine cigars, releases a 25th anniversary …

Mar 14, 2022