Detective Robert Cunningham's $3 Million Tip to Waitress Phyllis Penzo

Everyone knows that they should tip their servers well; in fact, the general rule, in North America at least, is 15% nowadays, but some people prefer to aim higher—or even tip with other gifts. 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

NY Lottery Winners Phyllis Penzo and Robert CunninghamIn 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 the bill. Though Robert was initially joking, Phyllis was hasty to agree. After all, the possibility of winning millions is much more tempting than a measly tip. The two chose the numbers together and waited hopefully for the draw.

On April 1st, 1984, Phyllis awoke to a call from Robert to let her know they’d just won $6 million. Initially, she was hesitant to believe him, as it was April Fool’s Day and she was certain it was just a rude prank. Still, he persisted. When she realised he was being genuine, she was filled with immediate excitement and woke her husband to tell him the good news: they were now millionaires.

With the winnings divided between the two of them, they were each walking away with $3 million. Since they accepted annuity payments, the two were set up to receive nearly $280,000 annually—making Phyllis one of the luckiest winners whose tickets were gifted.

How Did They Spend Their Winnings?

For Robert, he was eager to add more space to the home he and his family lived in. Since they shared the house with his wife’s parents, it’s obvious the house sometimes felt crowded. This way, everyone had space of their own.

Phyllis was immediately ready to shell out some of her millions, as she immediately invested in a new home as well as new cars for her family. Likewise, she took the opportunity to travel, as she was no longer restricted by the small wages that come with being a hard-working waitress.

It Could Happen to You Movie Poster 1994Movie Adaptation

A decade later in 1994, It Could Happen to You—a movie adaption of Robert and Phyllis’s story—was released, with the main cast featuring Nicholas Cage and Bridget Fonda. While the movie was based on the story of the shared lottery ticket, it didn’t stay true to what actually happened.

When interviewed by Entertainment Weekly, Phyllis expressed discontentment with the portrayal of a love story when that wasn’t her story with Robert at all. “Except for the part about us winning, it’s totally fiction,” she noted during the interview. Robert confirmed this when he mentioned that they were merely long-time friends who took the joke of sharing a lottery ticket very seriously.

It’s safe to say that the film was an extremely loose telling of what happened between Robert and Phyllis, as the two found the plot unbelievable and ridiculous when considering their friendship. Regardless, it was a box office hit that made nearly $38 million while in theatres, which is a substantial profit considering the movie’s $20 million budget.


Though Robert and Phyllis both indicated that winning the lottery didn’t change their lives too drastically, the luck of the draw definitely made it easier for them to live their lives just as they wanted to. Other lottery winners often say the same, though many very publicly fall off the deep end when faced with the excitement and responsibility of winning millions.

This story shows us what it means to be humble, even when experiencing the surprise of newfound wealth. Next time you dine out, remember to tip well, and maybe even throw a lottery ticket into the mix. You never know when you could change someone’s life for the better—though hopefully the recipient will be more appreciative than Tonda Dickerson, who won $10 million off of a tipped ticket and kept every penny to herself.

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