Remember This? What a Tip!

By: Brad Dison

On Friday afternoon, March 30, 1984, 55-year-old Dobbs Ferry Police Department Chief of Detectives Sgt. Robert Cunningham stopped into his favorite pizzeria, Sal’s Pizzeria on Neperhan Avenue in Yonkers, New York. He had been a regular customer for seven or eight years. Robert took a seat and began filling out a lottery ticket he had purchased early that day. As he thought about the numbers to choose, 48-year-old waitress Phyllis Penzo walked to his table and asked to take his order. Normally, this would have been the extent of Phyllis’s conversation with a customer.

Robert placed his order and he and Phyllis chatted briefly about the lottery ticket. Most of us have had the passing thought about what we would do if we won the lottery, and Robert and Phyllis were no different. Entertained by their conversation, Robert playfully asked Phyllis if she would like to pick three of the six lottery numbers. They quickly decided that the numbers should be 7-9-21-28-29-43. Phyllis picked numbers that had personal meaning to her. 7 and 29 were the month and day of her daughter’s wedding anniversary, and 9 was for the month that her granddaughter was born. Robert picked the remaining numbers, 21-28-43, off the top of his head.

Before paying for his meal and leaving a tip, Robert gave Phyllis a choice. Robert, who considered himself “an average tipper,” said she could have a “chintzy tip or go half on the card.” Phyllis was used to the customary 15 percent tip, but if they won, she would receive 50 percent of the winnings. Although Robert and Phyllis knew the odds of winning were against them—3,529,562 to 1 to be exact—Phyllis decided to forgo the tip. She said “I just wanted to take a chance.” Robert paid his bill, left no tip, and exited the pizzeria.

On the following day, the numbers were selected. Robert held out little hope of winning. When he finally got around to checking the winning numbers, he took out the card showing which numbers he and Phyllis had selected. He compared the numbers on the card to those reported in the news. The first number was 7. Robert looked on the card and their first number was 7. The second number was 9. Their second number was also 9. His heart beat faster with every number he compared. 21-21, 28-28. His heart beat even quicker. 29-29, and finally, the last number was 43. Robert and Phyllis’s last number was also 43. In stunned silence, Robert checked the numbers again and again. His mouth dropped. In disbelief, Robert had his wife, Gina, compare the numbers to see if he had made a mistake. There was no mistake, the numbers matched exactly.

Robert, who by his own confession was “really uptight,” spent the remainder of Saturday, all day Sunday, and Monday morning “shaking like a leaf.” He had to wait until Monday for the New York Lottery to certify him as the winner and to certify that no one else selected the winning numbers. If other parties had selected the winning numbers, the winnings would be split. Robert waited impatiently. He had taken the morning off to visit the lottery office. Finally, a lottery spokesman congratulated Robert. He was the sole winner of the New York Lotto.

All weekend Robert had thought about his agreement with Phyllis, the waitress. Technically, Robert had no legal obligation to share the jackpot with anyone. He could have easily kept the winnings for himself. In the end, with the support of his wife, Robert split the jackpot with Phyllis. The jackpot was paid out in 21 installments over 20 years. It was the third largest jackpot in the history of New York’s lottery at the time, and is considered to be the largest tip paid to a waiter or waitress in history. Phyllis sacrificed her usual tip, which would have been a couple of dollars, for fifty percent of $6 million.


1. Tampa Bay Times, April 4, 1984, p.1.
2. Newsday (Suffolk Edition)(Melville, New York), April 4, 1984, p.9.
3. Newsday (New York, New York), April 4, 1984, p.6.
4. The Journal News (White Plains, New York), April 8, 1984, p.70.

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