Doc What's Up?, Personal Essays

A Winner Every Time

Excerpt from Doc, What’s Up?

Even crooks, cons and hustlers can be elegant in their arts. It only seems to require a bit of chutzpah and sense of humor…

It was the Sixty’s and I was twenty years-old, working at Monticello Raceway in the Catskills or what we called the Jewish Alps. Here each summer, tens of thousands of escapees sought relief from the heat of New York’s Jewish ghettos. The Monticello Racetrack, which featured standard bred trotters and pacers on its half-mile oval, was a major attraction. Still, the amount paid for a winning race was minuscule, as were the wages for us part-timers.

A ticket seller’s work lasted only during racing hours, approximately four hours a night, six nights a week. Thus, it was no surprise that with fast money abounding, low purses and slave wages, off-color dealings were the norm amongst workers at the track.

There was little doubt that races were fixed. At least the drivers and trainers knew something that the betting public didn’t. The “know” was crucial to winning a race since the ones who were in the “know” seemed to win most of the time.

Those of us selling and cashing tickets rarely were apprised of the fixes but we had a more reliable way of cashing in. I called it “the hesitancy ploy”. It went like this:

The sucker bought two tickets at two bucks apiece, paying with a five dollar bill. The ticket seller would punch out the two tickets and then hesitate—as if the transaction was complete. Twenty to thirty percent of the time the harried horseplayer would run off to catch the next race, oblivious of the dollar owed him. If he didn’t run off, the seller would eventually get around to returning his change.

Cashiers did the same thing. When someone came to cash in his winning ticket for, say—$10.70—the cashier would present the ten and then stop, as if ending the transaction. Most of the time, the winner ran off to study the next race or calculate his victory and the cashier pocketed the seventy cents.

Another similar scam was an elegant yet simple ploy used by a few shady ticket sellers. If there were eight horses in a race, the seller would rotate his advice to each ticket buyer, advising the first buyer to hit on #1, the second buyer to hit on #2, and so forth. At the end of the evening, this would usually earn the ticket seller thirty to forty dollars in tips from the delighted patrons—winners because of his advice. This strategy was inevitably lucrative because someone had to be a winner. The winners thought the ticket seller was a genius and often became repeat customers for at least one more time.

About ten years ago, I was drinking the night away at the Harvard Club with a few of my New York venture capitalist buddies. I told them the story about running this con with my fellow ticket sellers during my early career at the horse track. It met with delighted howls and reminded one guy of a similar con used by his own New York broker.

His broker would go to seven or eight bars in an evening and buy drinks for certain patrons, pretending to get drunk himself. Then he’d advise those who’d listen to buy “such and such” stock. The trick was that at each bar, he advised a different selection of stocks. Once again, at least one of the stocks inevitably made money so he invariably got business from those he’d “let in on the skinny.” They thought he was a marvel and talked up his clairvoyance after their success, gaining further investment clients for him.

As I reflect on the art of con, I realize it is a fitting description of what financial advisors do all the time. When there are five hundred analysts with five hundred different opinions—someone has to be right. That analyst is hailed as a genius—and gets richer, at least for a while.

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