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Playing with the Pros

Our intrepid gambling columnist goes head-to-head with some of blackjack's top guns and holds his own
Michael Kaplan
From the Print Edition:
Kurt Russell, May/June 2006

It's early on a Friday afternoon and the Hyatt Lake Las Vegas crawls with card counters. Some of the smartest players in the business have swarmed this off-Strip hotel/casino, and, not surprisingly, many are operating under various pseudonyms. There's the diminutive and bearded Richard Munchkin. Stanford Wong, a famous blackjack strategist and author, is anything but Asian. And Anthony Curtis is not the child of a mother obsessed with Hollywood icons.

Big personalities are on the strut and cleverly conceived disguises abound: one player has a hippie-hair wig, a blacked-out tooth and the put-on demeanor of a pint-sized biker. Another's tipped his brownish locks with gray and inserted strips of baby-bottle nipples into his nostrils to pug out his nose. Under most circumstances, this crowd would represent a financial nightmare for any gambling establishment. Not today, however; these top-flight players are here to compete against one another rather than the house in the Ultimate Blackjack Tour.

The organizers—veteran gambler and Tour founder and president Russ Hamilton, entertainment attorney John Moonves and TV producer Houston Curtis—are offering more than $1.3 million in prize money for this invitational event. They're shooting it with the intention of landing a television deal, anticipating that the show will make blackjack as universally beloved as small-screen poker. Invited to help along this process is a who's who of Texas Hold'em stars: Phil Hellmuth, David "Devilfish" Ulliott and Annie Duke.

In today's seven preliminary tournaments, each player receives $25,000 in chips, betting limits range from $500 to $25,000, and a total of 30 hands will get played (with each table's lowest-stacked players eliminated after hands eight, 16 and 25). The object is to finish with as many chips as possible—which necessitates strategically betting in such a way that you maintain a lead over your opponents while minimizing your risk of ruin. The two players with the most chips at each table move on to a semifinal tourney. Then, the top six finishers from each of the seven days of play (filling a total of 42 seats, plus seven players who will have qualified online) earn a seat in the finals, scheduled to be taped two weeks later in Los Angeles, with a first prize of $300,000.

Several weeks earlier, when Hamilton asked me to compete in the preliminaries at the Hyatt, I jumped at the opportunity. In preparation, I spent a few weeks crash-coursing on how to play optimally (Wong's Casino Tournament Strategy has long been considered the bible) and got blackjack sensei Rick Blaine (author of recently published Blackjack Blueprint) to spend a couple nights running through some rudimentary concepts with me.

In Blaine's living room blackjack pit, I learned that it's best to start off slow but to quickly get aggressive if I'm behind as an elimination round looms. Blaine talked about the Secret Bet, a showy Ultimate Blackjack innovation in which each player has an opportunity to write down one bet and make it without others at the table seeing the amount being wagered (save it for the end, advised Blaine). And he offered strategies for holding on to a lead. "Usually," he said, "there are like results, meaning that if you win, your opponent will win as well. When you get ahead, mirror his bets and there's a good chance that you'll hang on to your lead." To say that the lessons make me seasoned, or even competent, is an exaggeration. Although I now feel as if I have a clue, I also expect to be pretty much winging it and do not anticipate getting very far against what promises to be stiff competition. Lingering in my mind, however, is one particular scenario: I have $30,000, another player has $20,000 and a third has $40,000. If we are going into an elimination round, what is the proper bet? I get all kinds of answers: $11,000 (to prevent the guy in last place from catching up), $10,000 (to push if you both win, and to give me the win in the event of a swing), and bet it all (some people can't help but go for broke). When I run into lanky Stanford Wong at the tournament, I pose the question to him. He answers without hesitation: "Nine thousand dollars is the proper bet."

I tell him that I don't get it. With that amount it seems as though I'd be setting myself up to lose if the person with $20,000 bets it all. "I don't mind answering your question," Wong replies, sounding a little testy. "But I'm not going to argue with you about it. We did computer simulations and came to this conclusion. That is the right bet."

Unconvinced, I pose the question to a guy who calls himself Hollywood Dave. Spiky-haired and displaying a flashy fashion sense that is straight out of the New Wave '80s, he offers a different take. "You make a big bet, like $12,000, press the short-stacked player to make a minimum bet [in the hope that you'll both lose, which would leave you with $18,000 and him with $19,500], and then surrender [removing your bet in exchange for giving up half of it]. It guarantees you the win. It is what's called a surrender trap."

Clearly, I have a lot to learn. And when I find myself sitting at a tournament table flanked by Wong and Anthony Curtis, along with poker star Phil "The Unabomber" Laak in the number one seat, I don't have to ask anyone to identify the underdog at this table. Miraculously, however, through a couple of smart wagers (one of which, Curtis marvels, is "the perfect-sized bet") and selective aggressive play, I wind up finishing second to the Unabomber and move on to the semifinals. If I win or place at the next table, I'll receive $2,000 and will be heading off to L.A. to take a shot at the $300,000. But it won't be easy. Among those I'll be up against are two notorious poker pros, Lane Flack and Alex Brennes, a woman named Ophelia whose boyfriend is a well-known card counter ("She's been well schooled," warns Blaine, shaking his head), and, scariest of all, a top-flight, muscled-up blackjack master by the name of Michael Castellana. Spotting his name on the seating list, Blaine ruefully says, "You're playing for second place." Fine, I think, second place will still get me to L.A., a prospect that begins to look more promising as the number of competitors at my table dwindles. In the 25th round, I double down with 15 (obviously an unconventional play, but perfectly sensible under tournament conditions and necessary to prevent my elimination). I draw a 5, dispatching the fourth-place player who leaves with a trail of artfully spouted F-bombs, all aimed at me, and I now feel as if I have a shot.

I've actually got the most chips at the table with only four hands to go. Castellana makes huge bets and goes on to win the next two hands (failing to follow Blaine's advice, I played more conservatively and now trot behind him in second place). Then, on the 29th hand, leading Brennes by $3,000 (and feeling as if L.A. just might be my destiny), I match his $4,000 bet. He doubles down and wins both hands. I lose and suddenly, going into the final round, I am in last place, trailing the second-place player by $9,000. I definitely got unlucky, but, in retrospect, made a critical error in failing to protect my lead by matching Castellana's big bets.

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