Phyllis Penzo was a waitress at Sal’s Pizzeria in Yonkers, New York, for twenty-four years. During that long tenure, she saw nice customers, difficult customers, generous tippers, and skinflints. But Robert Cunningham, a police detective from nearby Dobbs Ferry, was in a class by himself. Cunningham gave Penzo a tip of $142,857.50 a year for twenty years.
Cunningham, a thirty-year police veteran, was a regular diner at Sal’s, where he liked to order linguine with clam sauce and maintain a steady flow of banter with Penzo, other employees, and regular customers. True to his lighthearted style, Cunningham was making a sort of joke on Friday evening, March 30, 1984, when he offered his favorite waitress an unusual tip: a half-interest in a lottery ticket. Each picked three of the six numbers; Cunningham walked across the street and bought their ticket.
Penzo laughed, then forgot the incident until the next night, when the detective walked into Sal’s Pizzeria after work with the winning lottery ticket triumphantly clutched in his hand. It was worth six million dollars: three million for each of them. Cunningham, who ordinarily might have left a couple of dollars on the restaurant table, had no regrets about splitting the prize. After all, he says, Penzo helped pick the winning