Phyllis Penzo completely forgot that she’d agreed to choose lottery numbers with one of her regular customers in lieu of a tip — until Robert Cunningham walked back into Sal’s Pizzeria with a $6 million winning ticket in March 1984.
YouTubePhyllis Penzo, the New York waitress who won a $3 million tip in 1984.
Phyllis Penzo had been working as a waitress at Sal’s Pizzeria in Yonkers, New York, for 24 years when a chance encounter with a customer changed her life forever. Robert Cunningham, a police officer who frequented the restaurant, offered to split a lottery ticket with Penzo in lieu of a tip. Penzo completely forgot about the deal until Cunningham returned — holding a $6 million winning ticket.
Despite the windfall, Penzo didn’t quit her job. She said that she liked her regular customers too much to leave, and she continued working for three years despite her significant change in income.
She also bought a house, planned a trip to Hawaii, and — perhaps most remarkably of all — inspired a film starring Nicolas Cage and Bridget Fonda.
It Could Happen to You was only loosely based on Penzo’s story, as she and Cunningham didn’t really fall in love as depicted in the movie. But the story of one lucky lottery ticket was anything but fiction.
The Day Phyllis Penzo’s World Changed Forever
On Friday, March 30, 1984, detective Robert Cunningham of the Dobbs Ferry Police Department walked into Sal’s Pizzeria in Yonkers for a bite to eat. He struck up a conversation with Phyllis Penzo, a 48-year-old waitress who had worked at Sal’s for more than two decades. Cunningham was a regular at the joint, and he and Penzo had become friends over the years.
That night, Cunningham made an offer to Penzo: Instead of leaving a tip, she could help him choose three numbers on a lottery ticket. He would select the other three, and if they won, they would split the profit.
The New York TimesPhyllis Penzo in a 1984 issue of The New York Times.
“We were kidding around,” 55-year-old Cunningham told The New York Times in April 1984. “And I told her if we won it could be her tip. But she knows my word is as good as gold.”
As it turned out, those numbers — 7, 9, 21, 28, 29, 43 — were selected during the drawing the following evening. When Cunningham called Penzo the next morning to tell her the news, she thought it was an April Fool’s Day joke. But he returned to the pizzeria that night with the winning ticket in hand. He’d kept his word — and Phyllis Penzo had received a $3 million tip.
Phyllis Penzo’s Life After The Lottery
In the days following their win, Cunningham and Penzo were caught up in a media frenzy. “It seemed too good to be true,” Cunningham told The New York Times. But it was.
When asked what she would do with her share of the winnings, Penzo said, “I want to buy a house for my mother, my husband and myself and go to Hawaii. I don’t care about the volcano.” (Mauna Loa was famously in the midst of an eruption at the time.)
YouTubePhyllis Penzo and Robert Cunningham appeared in a New York Lottery commercial after their win.
Cunningham, meanwhile, planned to use his money for his children and grandchildren. He bought a boat and purchased a house that he shared with his in-laws. “It’s not like I got gold in my hair,” Cunningham told The New York Times a decade after his big win. “When you look at the spread, over 20 years, and what Uncle Sam takes, it’s not like you can go hog wild.”
In the end, Robert Cunningham and Phyllis Penzo each walked away with a payout of roughly $143,000 per year over a 20-year period — before taxes. While it was a significant amount of money for a pizzeria waitress, Penzo had no plans to quit her job, and she continued working for another three years. She briefly considered opening a restaurant but decided against it.
“[A]fter 27 years as a waitress,” Penzo told Entertainment Weekly in 1994, “you reach the age where you just can’t do those hours anymore.”
A New York State lottery commercial starring Phyllis Penzo and Robert Cunningham.
“I’m enjoying my life, and I’m finally enjoying my grandchildren,” Penzo told The New York Times in 1994. “Before, I was always working. Now, I take them all over.”
But winning the lottery wasn’t the end of Cunningham and Penzo’s story. In 1994, their lucky break was adapted into a Hollywood movie.
The True Story Behind It Could Happen To You
It Could Happen to You stars Nicolas Cage as police officer Charlie Lang and Bridget Fonda as waitress Yvonne Biasi, characters loosely based on Robert Cunningham and Phyllis Penzo. In the film, just as in real life, Lang offers to split a lottery ticket with Biasi in lieu of a tip. But that’s about where the similarities between the two stories end.
Onscreen, Lang and Biasi are each in doomed relationships. Lang’s greedy wife complains when she discovers that he actually plans to follow through on his deal with Biasi. In reality, Cunningham’s wife was more than willing to share. As Cunningham told Entertainment Weekly, “She said, ‘Hey, [Penzo] picked three of those winning numbers. She gets her half of the pot.’”
In the movie, Lang and Biasi both leave their partners and fall in love. As the film comes to a close, they get married and float off on a hot air balloon over Central Park. This was also entirely fictionalized.
TriStar PicturesBridge Fonda and Nicolas Cage in It Could Happen to You (1994).
Cunningham and Penzo stayed close friends, but they were happily married to their spouses and never even thought of pursuing a romantic relationship. “Ours is really a luck story,” said Penzo, “but the filmmakers turned it into a love story.”
“And I would never go up in one of those balloons,” Penzo added.
But even though Penzo and Cunningham didn’t end up together in real life, their story was still a heartwarming tale of friendship and honesty. There was no written contract between Penzo and Cunningham; he didn’t have to share his winnings. But he was a man of his word.
And unlike many lottery winners — like Tonya Dickerson, who was kidnapped by her ex-husband, or Jeffrey Dampier, who was murdered by his sister-in-law — Phyllis Penzo’s life didn’t take a turn for the worse. There were no acts of infidelity, no lawsuits, and no ugly battles with the IRS.
Penzo simply continued living as she always had, enjoyed time with her family, and shared her wealth with various charities. She died in August 2025 at age 91, and as her obituary states, she “will forever be remembered for her generosity and care for others.”
After reading about Phyllis Penzo and her $3 million tip, go inside the story of Stefan Mandel, the economist who won the lottery 14 times by hacking the system using basic math. Then, learn how Stephanie St. Clair became the “Numbers Queen” of Harlem.