The Good Life

Shortcut to Gambling Nirvana

Enlighten your path to enlarged winnings at poker, sports, blackjack and golf
| By Michael Kaplan | From Jay-Z, May/June 2009
Shortcut to Gambling Nirvana

Spend enough time reading this magazine and you will encounter stories about incredibly bright men with astonishing skills. Some of them seem like sleight-of-hand artists or mind readers. Others come across as out-and-out bandits. Mathematically astute and creatively resourceful about liberating the bankrolls of strangers, they are professional gamblers of the highest caliber. The best of them devise innovative techniques for beating the very games that most of us play only recreationally.

Never mind, for a moment, that gambling for entertainment and gambling to win are divergent pursuits. Wouldn't it be sweet to occasionally bust the bank in Vegas, make money on the odd round of golf or confidently clean up in poker tournaments? Assuming you have the aptitude to develop the necessary skills, if you make your money at a day job and visit casinos only occasionally, you probably lack the time and inclination to devote most of your waking thoughts to refining strategies for your propositions of choice. And, truth be told, most successful gamblers think of nothing more than ways of winning money.

Aiming to uncover a happy middle ground, the sweet spot where economy of time merges with successful wagering, we've picked the brains of four people who've devised shortcuts to finding edges at gambling's most commonly beatable endeavors: blackjack, poker, sports betting and golf. Their techniques won't turn you into an MIT card counter, or set you up to approach No-Limit Hold'em with the intuition of Phil Ivey, but they will allow you to play with a plan—and maybe even win a few bucks—while expending relatively minimal effort on learning how to do it.


Common wisdom holds that poker is a game of reading opponents and making a series of complex decisions in short periods of time. That's true for the best players. Top online pro Tom "durrrr" Dwan says that his success centers on a knack for making fewer mistakes than everyone else. Gifted pros play thousands of hands, see certain situations repeatedly and eventually develop techniques to deal with them. At its highest level, poker consists of subtle, cerebral offensive and defensive plays.

But what if you could win at Texas Hold'em with fewer complexities? What if you made your big decisions before the flop, before things got too tricky? And what if you executed bold moves that skilled players don't like defending against? Poker pros Blair Rodman and Lee Nelson have devised a strategy that is built on a foundation of pressuring superior practitioners and upending their decision-making processes by pushing all-in or folding, pre-flop, on every hand. This approach, based on just two decisions, disarms opponents and forces them to play in an unappealingly high-risk manner. Rodman calls it "Kill Phil," which is, not coincidentally, also the title of a book that he and Nelson coauthored.

At first, their technique (named in honor of Phils Hellmuth and Ivey) sounds unduly chancy. But after further inspection, it makes sense for inexperienced or outclassed players. It's a highly simplified variation on the approach that Chris "Jesus" Ferguson employed to great effect in the 2000 World Series of Poker championship when he found himself heads up against Texan T. J. Cloutier, who was clearly more seasoned and more conservative. Ferguson overcame his disadvantage by pushing all-in more often than would seem prudent, confusing Cloutier and leveling the playing field by ratcheting up the luck factor—albeit choosing to do it when he seemed likely to have better cards. This approach worked. When Ferguson attempted his final Hail Mary while holding just Ace-9, he hit his card and won the World Series bracelet. "Timid tournament players don't have a chance," says Rodman. "If you're not that good and not super aggressive, you bleed off chips to better players. The basic strategy here is to be very aggressive." It's fold-or-jam poker.

Rodman's plan can be retooled to work in no-limit cash games as well: players buy in for the minimum and fold all pre-flop cards until they catch a monster; at which point they push all-in. For tournaments, the approach entails playing tight at the beginning (when many chips aren't on the table) and opening up as blinds and antes rise and richer opportunities present themselves. "Opponents hate when you play this way," says Rodman, pointing out that it's hard for them to call a high percentage of all-in bets. "They say that it's not poker. My response is, 'OK. It's not poker. But it's the best way to attack the game if you're not experienced.' It forces players who are better than you to fold hands that they would normally play. You get very good players to completely change their games because they become scared of you. Doesn't that say something right there?"

Nevertheless, as Rodman readily acknowledges, this approach—which advises pushing all-in while holding not-so-strong cards like King-9 off-suit (with a medium stack, on the button, in an unraised pot) and doing the same thing with hands as low as Ace-10 off-suit against a late-position raiser—is a learning platform rather than a means to an end. He rightly notes that getting good at tournament poker requires players to mix it up with opponents and figure out the game; his strategy is something to use as you learn tournament Hold'em and refine your approach. "If you lack an executable strategy," he adds, "you'll never have the chance to move in all your chips, watch guys like Phil Hellmuth fold and hear them grumble when they see what you pushed with." Indeed, it may not be poker, but, as Rodman insists, "It's a lot of fun and you'll actually have a chance to make some money."

Sports Betting

Billy Walters is widely acknowledged to be one of the most successful sports bettors of all time. His wagering-derived income has provided a foundation for him to purchase golf courses, real estate and an impressive stock portfolio. But Walters' success with sports is predicated on more than simply picking teams that can cover the spread. He employs a staff of computer analysts, money runners and intuitive handicappers. On game days, Walters considers their suggestions and formulates advantageous wagers. In short, he succeeds by knowing more than the bookies. The likelihood of you or me pulling that off is a long shot. But there are other, easier ways to find an edge.

According to the pseudonymous Steve Fezzik, an insurance executive—turned—professional gambler who wagers $60,000 or so per betting day, a few things can be done to overcome the spreads. For starters, shop for lines as if you're shopping for a parity product and you're only concerned about finding the best price. When betting basketball or football, he says, you begin by figuring out the correct point spread. "In Las Vegas, the sharpest line is usually at South Point Casino; online it's at," advises Fezzik, adding that you use the information to uncover bookmakers offering better than baseline. "If you're betting against a local bookie, he's probably not moving the line very much. Just by knowing what the actual line should be, and making plays that will be in your favor, you're already realizing an advantage."

If you're betting via the Internet, Fezzik says, a good site to check out is "Bodog has two lines: one for recreational players and one for sharp players. The sharp bettor might get 6 on a game"—which is the correct number—"but they'll give 7 to the recreational guy." Similarly, betting an underdog on the first half of a game can be great when the favorite is giving up 1 point. Applied to the entire game, the single point is fairly innocuous, since games rarely finish as draws. "But if you're making a halftime bet, a half-point [which is what you get for half the game] is very meaningful: a lot of halves end in ties."

Even if you know little about sports, consider past performances and current expectations of teams. In other words, says Fezzik, "Once a team goes on a big streak, covering the point spread four or five games in a row, that is when you want to go against them. Usually it means that the oddsmakers started out underrating the team and will eventually come around to overrating them." That is your chance to step in and start taking advantage.

If you happen to be betting in, say, an office pool, where there are no point spreads, where everyone needs to simply pick winners and at the end of the season the person with the most winning teams gets the money, Fezzik suggests going for all the favorites along with a couple of slight underdogs. Why the dogs? "You're not the only one who's figured out that betting favorites is the way to have an advantage, but if you bet all favorites, you will tie with other guys who are doing the exact same thing. By throwing in a few close underdogs, you give yourself a chance to win."


Blackjack is a beatable game. Unlike poker and betting on sports and golf, it's purely mathematical. Play blackjack properly, for a number of hours, and you are favored to win money. But that's not as easy as it sounds. Mastering card counting—a system by which you track the cards that have been dealt and then make statistically advantageous plays based on the cards that remain—is fairly difficult and time-consuming. Furthermore, getting to the point where card-counting becomes so ingrained that it seems completely effortless and natural—and you avoid rousing suspicion at the casino—can be a lifelong endeavor. If you do get caught as a card counter, you'll be barred from playing blackjack, which is no way to enjoy a vacation.

Mathematician and former blackjack pro Olaf Vancura has devised a stripped-down solution, detailed in a book called Knock-Out Blackjack. His system is so mathematically simple that a fifth grader could do it. The most extreme card-counting plays will not be part of your routine (so you'll cut down on profits, but you won't get caught). However, you first need to perfect basic strategy by following the rules on those little laminated cards sold in casino gift shops—or found online at sites such as "People succumb to whims and superstition when they play blackjack," says Vancura, who has a Ph.D. in physics and a number of casino-game patents to his credit. "If you want to play this game successfully, you can't think in terms of patterns"—i.e., because you got dealt two 20s in a row, a third one ought to be coming. He smiles tightly, then says, "We try to make something out of short-term fluctuations that may not be mathematically sound."

Once you're settled in with basic strategy, Vancura's rookie system requires a very straightforward card-counting regimen: 2s through 7s receive a value of plus-1, 8s and 9s are zero, and 10s through aces are minus-1. In a single-deck game, if the count is below plus-2, you bet one unit (say, $25), and if the count goes to 2 or higher you bet two units (say, $50). That is it. For double-deck games you begin the count at negative-4 and raise the bet at plus-1; for six-deck games, the count starts at negative-20 and you begin betting two units when it hits negative-4. To become proficient at counting cards, go through a single deck and apply the above values to the cards as you turn them over. You should end up with a count of plus-4. Once you can do it accurately, in 30 seconds or less, you're ready to hit the tables.

In addition to using the mathematics outlined above, which in itself will put you in good stead, you might want to keep a side count of aces, estimate the number of cards that have already been dealt, and memorize and sometimes implement 20 or so deviations from basic strategy. Because you don't need to execute the mental gymnastics of full-on card counting (especially without the above additives), Vancura's approach allows for low stress and a slight edge over the casino. "Traditional card-counting systems are not fun; they're mentally taxing," says Vancura. "My system is accessible to every guy on the street who's not into studying for days on end before visiting a casino. My guy wants to have fun and play with an advantage."


Dewey Tomko is well known in elite poker circles. He's taken home three World Series of Poker bracelets and has snagged nearly $5 million in poker tournament winnings. But his surefire moneymaker is playing golf. Tomko has raked in the dough by looking amateurish on the course. This is not done for show. He actually lacks a powerful swing and doesn't have much of a long game. Spot him on the driving range, and he appears to be the kind of guy you'd love to bet against.

Maybe we see some of ourselves in him. A lot of us view our tee shots as being a bit raggedy and practically camp out on the range, hitting drives till our arms are sore, wanting nothing more than to look majestic and crush the ball. Not Tomko. He spends most of his warm-up time on the practice green. And he offers what sounds like the most obvious golf advice imaginable: "Getting the ball in the hole is what it's about."

What he means is that winning money at golf requires a short game that exceeds your long game. Then you win those Nassaus by turning every match into a short game. For instance, when going up against a long-ball hitter, Tomko always suggests that they play from as far back as possible. "That way," he says, "we're both going to have a hard time getting up onto the green." His counterintuitive point being that once he gets near the green, his game is going to be a lot stronger than his opponent's. If he can turn a match into a chipping contest, all the better.

Another critical point to winning money at golf is simply being honest with yourself as to how good—or not—you really are. Maybe because golf is such a tough game, maybe because it really comes down to being a contest against our previous scores, we tend to exaggerate our abilities. Not a big deal if you're playing for fun with a few pals; critical when you're playing for money and negotiating for strokes.

Because casual golfers tend to inflate their skills, just by having a true grip on your bona fide handicap, you are already playing at an advantage when it comes to matching up. And, advises Tomko, if you think you have a lower choke factor than your opponents, be sure to suggest betting with an invisible doubling cube. Basically, when any shot is in the air, anybody can shout out, Double! Then, before the ball lands, whoever hit it must agree to double the bet or concede it and pay off at the pre-double rate. This can turn a low-stakes round of golf into something much more expensive, and it's a bonanza for those who can maintain composure.

But as Tomko reiterates, success at golf wagering all goes back to your short game. As he explains it, "Look at Doyle Brunson: he's 75 and can barely walk, but he beats guys like Phil Ivey and Daniel Negreanu by playing to the safe part of the green, executing a good short game and letting the other guys beat themselves. They get to 100 yards from the green, laying 1, and they should par. Instead they bogey the hole." Tomko laughs softly and adds, "I guarantee you, right now, Daniel and Phil are out on the driving range, hitting ball after ball. That's fun. Having a good short game is not fun. It's work. I don't know how many thousands of hours I've spent on improving my short game. But if you want to win money playing golf, that's the way you do it."

Michael Kaplan is a Cigar Aficionado contributing editor.

Blackjack Poker Gambling

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