Cigar Aficionado

I've been writing Cigar Aficionado's gambling column for five years. I came into it knowing a fair amount about winning and losing money, but I wasn't especially seasoned at the tables. Over the years, I've become better versed in both sides of the gambling equation. I guess that's what happens when your job entails snooping around some of the greatest casinos in the world and engaging in a bit of gambling alongside people who really know what they're doing.

I've played craps with the Palms-owning Maloof brothers, practically sat in the vest pocket of David "Devilfish" Ulliott as he endured $60,000 swings in a pot-limit Omaha game, and spent an exhilarating Saturday afternoon in Manila with Alan Woods, one of the world's most successful horse betters. Without batting an eye, he blithely dropped a cool million that day, and said, "Well, if I'm gonna lose that kind of money, I'm glad to do it when it's being written about." Like all smart gamblers, he knows it's in his interest to look like less of a winner.

However, where you would have never found me during those five years is in a casino's blackjack pit, sitting at a felt-topped table, raising my fists in glory as I turn a 12 into 21.

It's because I never learned how to play blackjack—play the game well, that is—and that sinkhole of ignorance instilled a kind of 21 phobia in my soul. I just couldn't see sitting down to wager on a game where the casino has an edge and I haven't a clue.

So I avoided blackjack like hemlock, knowing full well that it's one of only three reasonably beatable enterprises in a casino (sport betting and poker are the other two), and a game that anyone with a serious interest in gambling should learn to play with an advantage. But I didn't think my math skills would be up to snuff for card counting. The few books I had read on the subject put me to sleep, and there always seemed to be an open spot at the poker table. My thinking went, "Stick with what you know." And I did.

Then, a year ago, I wound up doing a story on a female card counter who went by the name of Joanna Pandini. She was pretty amazing, managing to keep three continually changing sets of numbers in her brain, while acting like a ditzy, booze-swilling sucker at the table and winning a lot more than she lost. She inspired me to consider learning to count. Soon after I got a call from a guy named Rick "Night Train" Blaine. He's a card counter of note who's played on some of the big teams as well as for individual backers, and over the years has earned well into six figures from the game. He's also the author of a new book entitled Blackjack Blueprint (Huntington Press, 2006).

Blaine offered to teach me to count, using the system espoused in his book's pages. First, I wanted to see the book, just to make sure that my less-than-mathematical brain would stand a chance of absorbing his lessons, and that this undertaking wouldn't turn into a horrible embarrassment. Blackjack Blueprint proves to be an excellent book that combines a few existing techniques into a very manageable system for beating the casinos. Most critically, the tome is aimed at people such as myself who want to learn to count cards on the side, while maintaining a day job (which Blaine does as well). The fact that Blaine is a good guy and a patient teacher—I quickly began calling him my blackjack sensei—was a bonus. And the book's -friendly step-by-step approach parallels his teaching style.

For starters, I read key sections of Blaine's book, focusing on pages that taught me to play perfect basic strategy. Using various charts, I committed to memory the optimal play for every conceivable situation. That in and of itself was something of an eye-opener. I thought I knew how to play perfect basic, but I was wrong. You think you know? OK, quick, what do you do with two 2s against a 7? Split 'em. How about two 4s against a 6? Split 'em. Two 5s against a 9? Double down. The same hand against a 10? Hit it.

Maybe this stuff is easy for you, but it took me a while to get the preliminary moves down. A big help was a software program called Casino Vérité. It allowed me to play hypothetical hands of blackjack. Whenever I made a basic strategy mistake, the computer would emit a razzy-sounding buzz.

As soon as I got reasonably proficient at basic, Blaine invited me to his home, where the living room—cum—blackjack lab is, much to his wife's chagrin, outfitted with an almost regulation-size felt-topped table. He played dealer and divvied out cards to test my basic strategy play. He also gave me a couple of decks of casino-quality cards (they're thicker than the Bicycles you buy at your corner store) and advised me to learn to count down the deck.

This is at the crux of card counting: the cards from 2 through 6 are given a value of plus-1, 7 through 9 have values of zero, and 10-value cards through ace are minus-1. You literally flip through the deck, asg each card its value. The idea is to be able to do an entire deck in 15 to 20 seconds (at which point the count should be zero). I worked the decks and obsessively ran one of Casino Vérité's features: the Full Table Drill. The computer monitor presents a visual representation of seven blackjack hands; you track the cards and keep what's known as a running count (that is, the values for all the cards that have been dealt), always aiming to improve speed and accuracy.

Because most blackjack games are dealt out of six- or eight-deck shoes, one extra step of math is required to know how much to bet. The running count has to be divided by the number of decks remaining in the shoe. You do this by eyeballing the discard tray and making a damned good estimate of how many decks remain to be dealt. Extremely talented counters can tell you how many cards remain; guys like me are more than content to get the number of decks right. Then you divide this number into the running count to get a true count. Still with me? So, if the running count is six and three decks remain in the shoe, then the true count is two. The higher the positive count, the more you bet. Simple, right? Not for me. At least not at first.

Every week I'd spend a couple of hours in Blaine's living room casino, where he would comment on my progress, offer gentle advice and correct me when I was wrong. Occasionally he'd throw a curveball, grabbing my chips even though his hand had narrowly lost. Usually I'd be too focused on the counting to notice. That's when he'd let loose with a "baaaaah," which sounded uncannily like the mistake buzzer on Vérité.

"You just failed the MIT test," he said the first time, referring to the card-counting team immortalized in Ben Mezrich's best-selling book Bringing Down the House (Free Press, 2003). "You gotta catch those things."

I felt kind of dumb, but I was happier to have it happen in Blaine's living room than in a casino. Same when I'd make basic strategy errors, usually neglecting to split when I should have or goofing up on a surrender. The counting part of it, however, came to me with reasonable ease (and endless practice). Blaine would deal pretty much to the bottom of the shoe, and I became increasingly accurate. Things were going well enough that I planned on playing for real during an trip to Mesquite, Nevada. Following the completion of a practice session, I asked Blaine what he thought of the idea.

"You're ready," he said. Then he asked, "How much are you planning on bringing with you?"

"Not much," I told him. "I'm not looking to win or lose a lot of money. I just want to see if I can do it. They have $5 tables there, and I plan on spreading between $5 and $20 with a $500 bankroll."

Blaine told me to wait and he ran downstairs to his bedroom. He returned with five crisp $100 bills. He handed me the money and said, "OK. Now we're partners."

Following some last-minute advice from Blaine—look for good penetration (that is, dealers who cut deeply into the decks), drop out if the count goes below zero, try to find two-deck shoes (they'll be easiest to count)—things went reasonably well in Mesquite. Although I got completely crushed during a morning session and stood accused of card counting by a player at the double-deck table who didn't like my jumping out when the deck turned negative, I managed to win a couple hundred dollars. ittedly, I felt a little shaky and made a few tactical errors and definitely got lucky, but considering that it was the first time I'd played casino blackjack since a spring-break trip to Vegas in the late 1970s, I felt pretty good.

Blaine was pleased with the positive result, but we still had lots of work to do. Most importantly, I needed to incorporate a weapon into my arsenal of blackjack tricks: play variations. Ten years ago, card counters had to memorize upwards of 100 of these exceptions to the rule: moves that deviate from basic strategy, based on the count. For example, according to pure basic strategy, you never double 11 against the dealer's ace, but when you incorporate variations and the count reaches plus-1, you do double down with those cards; greatest of all, when the count hits plus-5 you split 10s and picture cards against the dealer's 5. This really makes other players at the table go insane; they will unabashedly gloat when you lose. But be warned: if you split tens or picture cards when the count is plus-5, you run the risk of giving yourself away as a card counter. In Blackjack Blueprint, Blaine has a list of variations that have been dubbed the Illustrious 18 by gaming theorist and card counter nonpareil Don Schesinger. They're the most important ones and, while difficult to learn, can be memorized by anyone who puts in the time and effort.

Although Blaine offers a good way of doing this—basically, learning the moves in clumps and grouping together variations that have certain similarities (for example, you stick 12 against a 2 when the count is plus-3, and 12 against a 3 when the count is plus-2)—it does get kind of tricky. Especially when you have to incorporate those variations into everything else that card counting involves, all the while looking like a casual blackjack player. It's along the lines of riding a unicycle while eating a hamburger and breathing fire. During a post-tutorial telephone call, I bitterly complain to the aforementioned Pandini about this particularly arduous task. She agrees that variations are tough to memorize, then sort of twists the shiv by acknowledging that she incorporates them totally instinctively at this point. Pandini maintains that she can't rattle off the variations but is incapable of playing without employing them. Great.

So I struggle through the variations, endlessly striving to commit them to memory, using flash cards as Blaine's book suggests, programming Casino Vérité to buzz me every time I make a mistake with the Illustrious 18. Then something strange happens: one night, as I'm playing Texas Hold'em for more hours than might be considered prudent (I'm looking at flops and my sleep-deprived brain clicks over to instinctively calculate them as blackjack situations), I feel that the variations and attendant blackjack moves are finally being tattooed into my memory. Beyond being disturbed by my inability to focus on the game at hand, I think that maybe one day I, too, will be able to tell people that I can't rattle off the variations but that not playing them would be as unthinkable as forgetting to breathe.

This past July, I headed to Las Vegas to cover the World Series of Poker championship and planned on putting my multi-tiered lessons to the test. But I failed. However, I honestly don't believe I did anything horrendously wrong. Blaine happened to be in town for some of those days, attending, of all things, a genealogy convention. He and his wife met me at the Palms, sat at my table, and watched me do most things right, yet I still lost big after positive situations failed to pan out the way they should have. That was the story of this trip: I would win when the counts sank and lose when they rose, but that can decimate your bankroll, because when the count is high (and, improbably, you are losing), that's when you are making your largest bets.

I dropped $500 (not a lot of money, and maybe not bad for someone who spent 10 days in Vegas, but, factoring in the $300 win in Mesquite, it represented more than one-third of my bankroll and I had expended a lot of psychic energy on trying to win) and came home feeling pretty disgusted. For a brief flash I even thought about giving up on blackjack. But then I attended a social gathering and happened to be drinking alongside a guy known as MIT Mike, a fearsome card counter who played on the original Ivy League team. I related my experiences. He smiled, sipped his drink and told me that it takes at least 100,000 hands before the luck factor evens itself out. In other words, what happened to me could have been nothing more than a standard deviation. Or else, I completely screwed up and played improperly and suck. Although I believe it was the former, I nevertheless hunkered down with Casino Vérité and continued to put in my weekly sessions with Blaine in preparation for another Vegas trip that had planned or the fall.

On my autumn trip, I stayed downtown and bopped between Binion's, the Golden Nugget and the Las Vegas Club, hitting the single-, double- and six-deck games. And hitting 'em pretty well. This time things fell into place nicely. I started with a playing bankroll of $300 and ran it up to $1,200 by jumping in and out of games as soon as they turned negative, counting intensely, ignoring players who got pissed off by my on-again/off-again betting. They kept talking about me hurting the rhythm of the cards. I was like, "Huh? Cards have no rhythm. They're randomly shuffled. The 10s don't know that they're supposed to be clumped together." Amazingly, dealers seem to buy into this screwball rhythm method as well. Late one night at the Nugget, a dealer advised me not to reenter if everybody starts winning, lest I hurt the table's rhythm. I met her eyes, smiled and said, "If you don't tell the cards what I'm doing, I won't tell them."

She looked annoyed, and I left 20 minutes later (after the count spiked and dipped again).

One night I beat up the Vegas Club a bit, but the following morning, I got spanked there and gave back a few hundred dollars' worth of chips. Intending to reverse things again, I returned to the casino and was about to sit down, when a big-boned gentleman in a suit greeted me. He seemed to be awaiting my arrival, and I thought he was going to offer me a big, fat comp. But there was something else on his mind. "I saw you playing here last night and I know what you're doing," he said. "You're welcome to play any other game in the casino, but we don't want you playing blackjack anymore."

I tried to weasel my way back into the pit, truthfully pointing out that I had given up a chunk of my winnings just a dozen hours earlier. But he seemed unimpressed. It was nonnegotiable. No more blackjack for me at the Vegas Club. While feeling bummed at being backed off from a good game, I was also a little thrilled. Walking out of the casino and onto bustling Fremont Street, I felt as if I had just hazed my way into an exclusive club. The ousting felt like proof that I was doing something right. Then I set my sights on a more welcoming cluster of bright lights and green felt. v

Michael Kaplan is Cigar Aficionado's gambling columnist.