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The ambiguity of the hustle 

During my (mostly misspent) youth my hangout joint was the local bowling alley. I got to know guys who seemed to live in the alleys, didn’t appear to have jobs or obvious means of support. Their main income was from bowling – just like their brothers in the pool halls and their cousins who were playing chess, gin rummy and backgammon. They were hustlers, all of ‘em. They are a breed, a very special one.

I spent time trying to run a hustle myself. When I was 20 I looked about 15. It helps when you are the innocent one. I did okay, made a few bucks, but it was clear it wasn’t going to work. For one, I was supposed to be a full-time student and for another I kept feeling sorry for my marks – and that disqualifies you. 

While I couldn’t pull off this piece of cozenage, I never lost my fascination with hustling. Is it cheating? I don’t think so. In cheating, someone is using devious and covert means. They know your hole cards, have inside information, snuck in loaded dice, whatever. Hustling is when one person is more skilled than another but only one of them knows it. This feels different to me but there’s a lingering ambiguity.

Let me tell you a story from back in my Brooklyn days. My wife and I were heading back after a stroll along the boardwalk at Coney Island. In a small park there were several large concrete walls, each forming the business end of a one-wall handball court. We stopped to watch and I realized that many of the players had bets on nearly every game.

One-wall handball is exactly what is says it is. You hit the ball with your hand and there is only one wall. The object is to hit the ball to the wall on the fly and try to do so in a manner that minimizes the chances of your opponent doing likewise. The ball may bounce once between the wall and your hand; two bounces and you lose the point. In the more sophisticated versions, the game is played in expensive, specially constructed courts that are literally large rooms where all four walls can be used, rather like squash. One-wall handball, however, is for the street not the country club.

My attention was grabbed by two pretty athletic looking guys in their mid-20’s who were playing against each other for $5 a game. Among the crowd of onlookers there was this big guy in a suit. He made me think of the Big Julie character in the musical Guys and Dolls. He was a good six-two, looked and sounded very Noo Yawk, and had an engaging clumsiness about him that, as I would soon see, was but a well-crafted illusion. 

Julie started kibitzing with the two guys who did the only thing Brooklynites do, told him to either come out on the fuckin’ court or shut his fuckin’ mouth. Julie stepped on the court, put up his five bucks, played a decent game, but lost by two points. One thing led to another, and pretty soon they’re playing for $10. Julie won a couple and he lost a couple. I was standing there grinning like the Cheshire cat. My wife, who doesn’t “get” this slice of life, wanted to leave. I told her she could if she wanted but there was way I going to miss this.

After a bit Julie has taken off his jacket, shirt and tie but is still playing in street shoes. He is also now playing singles against the other two guys at once and the stakes have crept up to $20 a game. Julie is winning about two out of three games, but usually only by a point or two. The stakes move to $50 for the last game. It is strictly no contest. Julie is a master. Fade shots fall like a dying quail untouched, spin shots twist off the wall at unreachable angles, power returns fly by off-balance opponents. Julie pocketed the $100 (along with the other $100 or so he had already won), put on his shirt, his tie, his jacket, thanked the two guys for a terrific set of games, and left. They stood there kind of bewildered, trying to figure out what hit them.

Similar dramas are played out daily in bowling alleys and pool halls, on golf courses and at chess boards, on basketball courts, squash courts, and a dozen other venues. There is always the question of whether someone is cheating you, hustling you, or merely better than you. It seems pretty clear that Big Julie is a hustler but, is he a cheat? He doesn’t feel like one – not to me. He’s an engaging character whose skills are admirable. But suppose we discover that he had slipped a drug into his opponents’ water. Now he’s a crummy, low-life slug.

Guys like Julie have become pieces of American iconography. The lore of gambling is filled with stories of the exploits of these weird and wondrous characters. The movie The Sting was based on one long, deliciously crafted scam. In it we identify with Paul Newman and his crew but only because their mark is a low-life scumbag. If the sting was on a little old widow we’d feel differently.

One of the true legends of this genre was “Titanic” Thompson, a large man of considerable wealth with an insatiable appetite for a wager. Thompson reportedly was the first to suggest what has now become the prototype of the totally nutty bet: which of two rain drops would get to the bottom of a window pane first.

Thompson, who in his long career concocted and won some truly bizarre wagers, habitually tiptoed along the line that separates a clever hustler from a flat-out cheat. He once won a bet that he could drive a golf ball over 600 yards. He waited until the dead of winter when he smacked a ball across a frozen lake where it skidded and bounced for nearly a mile. Did Thompson cheat the guy or merely outsmart him? What if had won the bet by going to a regular golf course in the spring but smuggled in a juiced golf ball? Now he feels like a cheat and I don’t like him anymore.

Poker legend Amarillo Slim once beat a champion ping-pong player by convincing him to play for money but using rackets that Slim chose. Slim showed up with cast-iron skillets. It was no contest. The champ wanted a re-match. Slim said “fine but the same deal holds.” The ping-pong champ spent the time practicing with iron skillets. Slim showed up with coke bottles. No contest. Was Slim a cheat?

Finally, before we leave Brooklyn, a question: What do the two guys Julie took for $200 think?

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