Spend enough time playing high-stakes blackjack and you’ll learn a lot about yourself plus plenty about others. One thing you learn very quickly is what it feels like to win and lose a lot of money.
My Toughest Blackjack Losses
In the early 2000s, I was part of a large card-counting team backed by a group of Wall Street traders. We were said to have a $1 million bankroll. The best part was flying into Las Vegas at the team’s expense, going from the airport to a guy we’ll call Clarence, and getting a $50,000 bankroll to play blackjack. At the end of the trip, you returned to Clarence’s house and turned in your winnings.
Sadly, you didn’t always come out on top. One of the toughest moments happened at the Palms. I wrapped up a session with a couple thousand dollars in profit, had the dealer cash me out, and got ready to leave. Then a man sat down with a striking blonde who had impressive cleavage. He signed a $75,000 marker and got a big stack of chips. Thinking that with the attention on the flashy woman and the expected big bets, security would overlook me, I decided to play one last shoe.
In less than 30 minutes, all I had in front of me were two busted $10,000 straps.
Big mistake. The count quickly went through the roof, I anted up for two spots at $1,500 per hand and got slaughtered. The dealer kept drawing 10-value cards. I received a parade of 3s, 5s and 6s – usually accompanied by a 10-value card of my own. In less than 30 minutes, all I had in front of me were two busted $10,000 straps. I lost 20K-plus. It felt terrible. And the dealer made me feel worse, lamenting over how unlucky I’d gotten, insisting that he’d never seen anything quite like it – the way I refused to lower my bets or play just one hand. But I couldn’t. The math favored me. Never mind that it betrayed me.
On the upside, I called Clarence and told him what happened. He sighed and said, “Come by. I’ll reload you. You can grind back up.”
My memory is fuzzy, but I like to think that I received another 50K and more than made up my losses that weekend.
My Biggest Blackjack Wins
On the other side of it, I’ve had my share of big wins. Including one in Monte Carlo (where I wound up with a large, rectangular chip, known as a plaque, worth 20,000 euros – plus thousands in random chips) and another in the Bahamas where I brought down the house as a crowd behind me back-bet on my plays. That is, they saw me on a streak, thought I couldn’t lose and started betting on my hands. Not exactly conducive to maintaining a low profile, but, whatever… Luckily, I kept it going through the shoe, won 10s of thousands for myself (actually, for the team) and maybe more for others.
Soon after, casino management realized that I was counting. I got a shoulder tap and was told, “Mr. Kaplan, we appreciate your business. But your blackjack action is a little strong for us. You can play any other game. But you can’t play blackjack.”
Happily, they were nice enough to not 86 my comps and I spent the rest of the weekend enjoying a free vacation on the casino’s arm. A joint in Connecticut proved less understanding. After they busted me for winning sessions of counting, all my comps froze and it became clear that I ceased being a welcome guest. My wife and kids happened to be with me on that trip and I made an excuse to the kids about the hotel having an electrical problem. We hightailed it to Mystic Pizza (the nearby pie spot that inspired a movie of the same name). Yes, I took the money and ran.
World’s Greatest Blackjack Wins and Losses
Of course, my blackjack wins and losses pale against the greatest ones in the game’s history. Consider the finance executive Michael Geismer. Using nothing more than a basic-strategy card in a Vegas casino, he started with a $10,000 marker and ran it up to 460K by night’s end. Next morning, he took the casino for another $250,000 and lucked into a $710,000 payday – while playing with a negative expectation. Dana White, beloved by some as the president of UFC, is despised by at least the Palms in Las Vegas. It has something to do with his winning $2 million, getting backed off, somehow being invited back for a re-match and taking down another $2 million. He did not get a third chance.
Then there is Don “Motherfucking” Johnson, a man who snagged 10s-of-millions from the casinos and was comped like a king. After winning bundles through a combination of card counting, hole carding, ace sequencing and a move known as “card eating” (in which he never varied his bets, so as not to rouse casino suspicions, but had hot chicks sitting in on the table and making minimum wagers when the count dropped, in order to drain the bad cards).
He later teamed up with two of the world’s sharpest advantage players and they went on a global rampage, playing with a computer driven system that took advantage of rebates (buy in for enough money and the casino refunds a percentage of your losses) and set parameters for when it would be advantageous to stop for the day – whether ahead or behind.
I announced that I would do a shot of cognac and then make my decision on the hand. I drank the drink, took my time, seemed to be thinking about it and doubled down.
Sometimes, making the big wins necessitated putting on a bit of a show. Johnson recounted for me the time at the Venetian when he had $50,000 in the betting circle, was dealt a 17 and one of his shuffle-tracking partners signaled that he should double down. “Obviously the card was a 3 or a 4, or else I would have not gotten the signal,” Johnson told me, adding that he needed to make himself look reckless in order to pull of the audacious play. “I announced that I would do a shot of cognac and then make my decision on the hand. I drank the drink, took my time, seemed to be thinking about it and doubled down. Of course, the next card was a 4. No doubt, heads were spinning upstairs in surveillance. Surely, the pit told them that I was fucking blitzed. Clearly, I wasn’t.”
Ironically, one of the most outrageous nights at the blackjack tables also happens to be the one that made the game less viable for some advantage players. It was on June 28, 1997, when Mike Tyson fought Evander Holyfield at the MGM Grand. Tyson bit off a piece of Holyfield’s ear and the fight got cancelled; all hell broke loose in the arena and in the casino.
There are those who believe that the post-fight mayhem at MGM marked the end of a golden age.
Up until that moment, betting was sky-high. John Chang, a member of the famous MIT blackjack team and the model for Kevin Spacy’s character in the movie “21,” told me, “The table was full, everyone was betting yellows [$1,000 chips]. I’ve never seen the action so big. I was ahead $70,000 on the night. Then the bite happened, there was a riot, tables got overturned, chips were stolen out of racks.”
Play eventually resumed, but surveillance instantly tightened, and life got worse for blackjack hustlers. As put by Chang, “Our best players burned out faster than we could train new ones.”
There are those who believe that the post-fight mayhem at MGM marked the end of a golden age. But there are others, including Johnson and his cohorts, who know that there’s always a new way to crush the games that gambling joints offer up. “There are so many casinos in the US,” masterful advantage-player James Grosjean told me, while munching a slice of pizza on the Atlantic City Boardwalk, after getting booted from what had been one of Donald Trump’s casinos in AC. “On any given night, there are more games out there than I could possibly whack.”