Gamblers playing casino games at an advantage love to camp out at the tables. They slowly make their money, hand by hand, as they deploy winning strategies that have them operating with an edge at games like blackjack, three card poker and even slot machines.

Unfortunately for them, casino bosses do not share their enthusiasm. 

In fact, casino bosses want nothing to do with advantage players and aim to get them out of their casinos as quickly as possible. Techniques for that range from gentle backoffs – a player being told, “Your action is a little strong for us; you can play any game in the casino, but you can’t play blackjack” – to the rigid 86ing: Come back again, even for a soda, and the police will be called.

Counting Cards

During a few years of serious card counting, I endured my share of backoffs and I came to understand why those in the game go to elaborate lengths to prevent such events from happening. 

To that end, I enjoyed dropping into Las Vegas on a Friday night, getting a few hours of sleep and hitting the casino with a cigar in my mouth and the demeanor of a hard partying drunk in late-night/early-morning mode.

In fact, I was well rested and trying to seem as if I had been going at it all night. Pit bosses were generally happy to see a player in that condition and I figure that it routinely bought me some time.

But that’s mild in comparison subterfuge deployed by others. One of my favorite APs in disguise stories comes from John Chang. A founding member of the famous MIT blackjack team, he inspired Kevin Spacey’s character in the movie 21. But he didn’t have to become  Hollywood famous to be casino notorious.

Chang had his share of gambits – including pretending to be the deep-pocketed nephew of a Chinese computer mogul – but the most outrageous one came when the heat on him turned so intense that desperate measures were required.

At one point, it became clear that dressing as a female would be the best way for Chang to be able to play without getting thrown off the blackjack table.

“Cross dressing worked in the Bahamas and Illinois,” Chang told me when I interviewed him for the now defunct Men’s Vogue. Admitting that a baby face did not hurt him in pulling off the gambit, he added that in at least one casino, something gave him away. “At Taj Mahal in Atlantic City, they were looking at my hands. An Asian host came over and whispered in my ear, ‘We know who you are.’”

Security loomed. When Chang rose to leave, a guard said, “Lose the pearls, Esmerelda.”

As Chang remembers it, “I had to run around the casino in high heels and make sure they weren’t following me.”

Blackjack card counting

Wonders of Wheelchair

A fellow blackjack advantage player, who had the well-earned nickname of Wheelchair, could not be chased around the casino because he gave the appearance of being unable to walk.

Though he was perfectly mobile, the man rolled around in a wheelchair, pulled up to blackjack games and made it so that he was nose level with the table’s rim. That afforded him a perfect vantage point for hole carding – that is, seeing the bottom cards of sloppy dealers. 

Because he did not appear to be slouching, abetted by the fact that casinos would be  loath to insult a handicapped person, he managed a double whammy: Perfect hole carding position and an act that all but guaranteed he would not be backed off from the game.

Team Duynamics

A woman I know who played on one of the most notorious blackjack teams in the country during the early 2000s used her youthful face, tiny backpack and slender physique to look like a trippy rave kid who was gambling away her wealthy father’s fortune.

Taking casino costuming to the next level was a blackjack contingent known as the Church Team and famous for elaborate disguises. One player had get-ups that ranged from that of an Indian businessman (complete with a turban and a suit) to a rapping gangsta to a makeup wearing goth.

Another member of the team employed a quick change to extend his play. In a single night, he looked a little rough with a scruffy beard and the demeanor to match. Then, after getting booted from every casino in Tunica, Mississippi, he shaved the beard, put on a suit and tie, and returned as a completely different person. It worked!

In Atlantic City, he told me, “I played the persona of an aggressive Russian guy. I’d point at the pit boss and tell him to get me water.”

    James Grosjean, one of the most prolific and most inventive players out there, had a costume that convincingly turned him from computer nerd to gnarly biker – complete with a sleeve of tattoos. Kelly Sun, who pulled off a multi-million-dollar baccarat play, was known to hire professional makeup artists to tweak her appearance.

But sometimes, the disguises don’t need to be so elaborate if you have the skills to match the subterfuge. I remember hearing about a super sharp blackjack player who would situate himself within eye shot of a targeted table, calmly read the day’s newspaper and sip coffee. He resembled a reluctant gambler looking to keep up on current events. 

But he was actually card counting from a distance, discreetly looking up from a corner of the paper. As soon as the count turned favorable, he’d fold up his reading material, leave behind the java and buy into the blackjack game, thus playing only when he had an edge and thwarting the casino’s likelihood of picking him off as an advantage player.

Crafty Costume

Back when I interviewed John Chang for Men’s Vogue, the magazine was eager to photograph him for the article. I figured that maybe he’d be shot in shadow, but he had an idea that would pay off for him.

Chang requested that the magazine load him up with pricy fake facial hair – a fu manchu, a van dyke, a dramatic mustache – that he would get to keep after using the array to hide his identity in the photos.

The editors agreed and he got his hairy camouflage that no doubt faked out casino bosses. Crafty advantage players always find a way to win. 

Michael Kaplan is a journalist based in New York City. He has written extensively on gambling for publications such as Wired, Playboy, Cigar Aficionado, New York Post and New York Times. He is the author of four books including Aces and Kings: Inside Stories and Million-Dollar Strategies from Poker’s Greatest Players.

He’s been known to do a bit of gambling when the timing seems right.