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Winning at the Big 3

Everyone's got a buddy or an Uncle with winning gambling strategies, here are some that actually work.
Michael Kaplan
From the Print Edition:
Dennis Hopper, Jan/Feb 01

We've all been there: sitting in a casino, throwing good money after bad, trying to beat the odds at a blackjack table. It's small consolation that everybody else is getting massacred as well. Or almost everybody else. One guy hunches quietly in a corner seat, observing everything with an air of snooty detachment. He's scoring 17s, 21s, 19s, getting all the right cards, hitting with uncanny accuracy, and raising his bets at precisely the opportune moments. You and the others double down with 11s only to get dealt fives. You hit with 15s or 16s and draw picture cards. Once-handsome skyscrapers of chips slowly disintegrate into shabby little hovels of $1 and $5 disks.

Something is obviously wrong here, and you can't blame it all on rotten luck.

Skill, systems, strategies and discipline -- all of those things make the difference between a player who enters a casino to throw money around and one who goes in with the intention of actually winning. Sure, for most of us, gambling is entertainment -- and you probably have little intention of earning a living from playing cards -- but it's inarguable that winning is a hell of a lot more entertaining than losing. I decide that I'd like to be the detached guy who seems to have ESP and more chips than anyone else at the table.

Armed with $500 of Cigar Aficionado's money, I head to Las Vegas and check into the Mandalay Bay Hotel & Casino. I am a man on a mission. My intention is to tilt odds in my favor by getting inside the heads of three successful gamblers: a blackjack player who always doubles down at the right moment, a roulette expert who capitalizes on each of his wins, and a craps shooter who bets intelligently rather than randomly shoving chips around the baize-topped table. The goal here, at least for the time being, is not to get rich but to get smart. Rather than being a willy-nilly player who has a blast at the tables and goes home broke, my plan is to plug into the game, to win money, to transform into the rare kind of player whom people look at with curiosity and envy.

I want to be a winner.

Larry Grossman hosts a local radio show called "You Can Bet On It!" (archived at He's interviewed every gambler imaginable and has done more than his share of wagering. One thing he's discovered about roulette is that, over the long haul, players cannot possibly win. "You can beat a session of the game," he says. "But you can't beat the game itself. The zero and double-zero tilt the odds in the casino's favor. While some guys talk about finding roulette wheels where the bias is slightly off and favors the player, you'd need to be an MIT graduate who's devoted his life to finding these tiny biases in order to capitalize on them. And who has time for that? Life is too short."

The system that Grossman proposes is simple. "You start with, say, $40 in chips," he begins. "You place one chip on each of five numbers. You give yourself eight chances for one of your numbers to hit. When the number hits, you collect 35 chips. So, on the next spin, you put four chips on each number. If you lose on that spin, you go back to betting one chip on each number and you still have a $15 profit. If you win with four chips -- the payout would be $140 -- you raise your bets to $10 on each spot. The payout there is $350. That's real fun and you are pretty much guaranteed to go home a winner for the night. But you're now putting up 25 chips on each number. Let me tell you -- as somebody who reached that point one time -- your heart is pumping fast; you're getting the ride of your life; a nuclear bomb could go off and you'd still be standing there, waiting to see whether or not your number hits." What if it doesn't? "You always return to the one-chip bet."

He relates this in the lounge area of The Orleans Hotel & Casino. Just before we head over to a wheel, he adds, "Roulette is a perfect game for somebody who is drunk, stoned, or doesn't know how to play anything else. It's a no-brainer. You relax, put your chips on numbers, and the dealer does everything else. There is no work involved."

We pull up our chairs and sit down at the wheel; each of us fronted by stacks of 40 chips. As we select the numbers we'll play throughout this session -- I hope 32 will be luckier for me than it was for O.J. -- Grossman says, "The beauty of this game is that you can be seated right next to a guy with a Ph.D. in mathematics and you both will have the same chances. There's something nice about that."

The wheelman at the table is a slightly bitter but boyish-looking fellow who seems to enjoy it when people lose. He gets a kick out of the way we obsessively cover our pieces of real estate on the roulette board, laying down $1 chips with overblown care. A few spins in, the strategy pays off for me. But then, when I quadruple each bet, the little marble settles into the number 16 slot -- definitely not one of my numbers. The dealer sweeps his board of chips, looks at me, and says, "I guess you won't be able to buy that car you had been counting on." I play the good sport, smile, and go back to betting single chips.

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