It is not easy for a lifelong gambler to isolate the stupidest bet he has ever made, but one that still haunts me is the 1979 World Series.
I invested $1,000 on Baltimore to take the series against Pittsburgh, and the Orioles put me in an ideal situation when they captured three of the first four games. I could hedge my position by making a small wager on the Pirates, who were now 8-to-1 underdogs, so that whatever happened I could not lose.
Of course, I didn't do anything so intelligent. Instead, I congratulated myself for perceiving that the orioles were such a superior team, and continued betting them in each of the remaining games of the Series. When the Pirates won them all, I managed to lose my skirt in a can't-lose situation.
I was reminded of this debacle as I sat in the Gulfstream Park press box this morning listening to the Old Timers' Story Hour. Some venerable handicappers here regularly regale each other and their younger colleagues with tales of the great highrollers of the past, and a reminiscence by Sam Engelberg of the Miami News perfectly embodied the lesson I should have learned in 1979.It will be forever emblazoned on my memory.
Early in 1948, Engelberg related, a department-store buyer named Harvey made a number of substantial wagers on Thomas E. Dewey to win the presidential election. Harvey stood to win $100,000 if he were right, and as election day approached, that seemed to be a foregone conclusion. In gambling circles the odds on the election had skyrocketed to 10 to 1, and even at that price almost nobody was willing to bet Truman.
A respected New York bookmaker knew of Harvey's enviable position, and on election night he approached the gambler with a proposition. "Tell you what I'll do," he said to Harvey. "I'll let you bet me $15,000 on Truman at 7 to 1. That way you've got a sure thing. If Dewey wins you make $85,000, and if Truman wins you don't lose anything."
"You're trying to rob me!" Harvey shot back. "You know the price ought to be at least 10 to 1."
"I know it," the bookmaker conceded, "but tell me where you can bet $15,000 to 10 to 1 and know you're going to get paid. I'll post the cash in advance."
Harvey was unmoved. "You're not going to cheat me," he said. "I'm not going to take the worst of the odds."
The next morning Harvey woke up to learn that Harry Truman had won the election. Engelberg saw him that day and recalled, "He looked as if losing that bet had made him physically ill. His skin was practically green. But he told me he was going to go to Las Vegas to recoup."
Harvey went to Vegas, but he did not recoup. He lost $50,000, almost all of his worldly worth. On the flight back to New York, he slumped in his seat dead of a heart attack, demonstrating that for a gambler excessive greed can be fatal.