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  1. Such is the story of lottery winners Robert Cunningham and Phyllis Penzo, in which a shared gift in lieu of a tip turned out much better for both of them. A Dine-In Lottery Win In 1984, New York City detective Robert Cunningham was dining at Sal’s Pizzeria in Yonkers when he suggested to his waitress and long-time friend Phyllis Penzo that the two split a lottery ticket instead of tipping on ...

  2. Dec 31, 1998 · 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.

  3. Mar 1, 2022 · In 1984, detective Robert Cunningham from Dobbs Ferry, New York, won a lottery payout and split it with his waitress, Phyllis Penzo, as he'd promised. In the movie, the cop promises to split because he has no money for a tip; in real life, Cunningham promised it because Penzo helped him pick the numbers.

  4. In 1984, Phyllis Penzo was a waitress at a pizzeria commonly frequented by Yonkers, New York, police officers. In March of that year, Officer Robert Cunningham, a regular patron and longtime friend of Penzo, suggested that the two split a lottery ticket, each of them choosing three of the six numbers, in lieu of his leaving her a tip.

  5. Apr 2, 1984 · April 2, 1984. Waitress gets $3 million tip. YONKERS, N.Y. -- Police Sgt. Robert Cunningham offered a waitress at his favorite pizzeria half of his lottery ticket instead of a tip. She accepted ...

  6. Apr 7, 2024 · But other than the pair’s occupations and the lotto ticket tip, the rest of the plot is pure Hollywood rom-com. “No, I didn’t marry Bob,” Penzo said. “And I would never go up in one of those balloons!” Watch a TV commercial featuring Robert Cunningham and Phyllis Penzo

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  8. Feb 10, 2024 · Yes, ‘It Could Happen to You’ is partially based on a true story. Penned by the talented screenwriter Jane Anderson, the film takes inspiration from the life of Detective Robert Cunningham of Dobbs Ferry, who won $6 million at the New York State Lotto prize in 1984 and decided to give half of it to Phyllis Penzo, a waitress employed at Sal ...