When a police detective offered a Yonkers waitress half of his lottery ticket instead of a tip, it was a simple act of generosity to a long-time friend. But his decision would not only impact both of them for the rest of their lives, it would also inspire a popular romantic comedy starring Nicholas Cage and Bridget Fonda. “It Could Happen To You” follows the pair as they become millionaires and fall in love, but as Sgt. Robert Cunningham and Phyllis Penzo explain, the Hollywood version of their story is purely fictional.
Cunningham, a Dobbs Ferry police detective for more than 30 years, was a regular patron of Sal’s Pizzeria in Yonkers. A favorite of local police officers, he frequented the spot for their linguine with clam sauce and to visit with his friend, waitress Phyllis Penzo. In March 1984, Cunningham visited the restaurant and placed his usual order with Penzo. At the end of his meal, instead of leaving a tip, he offered her half of his lottery winnings if she helped him pick out the numbers. She agreed, and the pair filled out the blank New York State lotto card together.
From Waitress to Windfall
Cunningham’s impromptu decision led to a life-changing $6 million win. True to his word and committed to honor his promise to Penzo, he split his winnings. Each of them netted $3 million paid out at $285,715 per year over 21 years. At the time of their windfall, Penzo had worked at Sal’s Pizzeria six nights each week for the previous 24 years. When she received a call at 9 a.m. on April Fool’s Day, she thought it was a joke.
“I was still asleep,” she remembers. “I said, ‘Don’t bother me now.’ ”
But Cunningham was swift to convince her that he was giving her half of his winnings from the $1 ticket (approximately $18 million in 2024). Penzo screamed and woke her husband as she realized her friend was telling the truth. When interviewed by People Magazine shorty after their win, Cunningham explained that he knew right away that sharing his winnings was the right thing to do—and that his wife agreed.
“If I say I’ll do something, I do it. I hope money never changes me,” he said. “I told [my wife Gina] I had a partner and we were splitting down the middle. That was it. That is how our family operates.”
Both Penzo and Cunningham also asserted that they would continue to work despite their newfound wealth. At the time, their plans for how to spend the money were modest and family-focused. Cunningham planned to expand his family home in Dobbs Ferry and Penzo intended to use her share to buy a house in Yonkers with her husband Robert.
The Hollywood Treatment
Eight years after the winning numbers were drawn, TriStar Pictures began shooting a Hollywood adaptation of Cunningham and Penzo’s story. When films are based on true events, the plot lines typically closely follow the true story so it accurately reflects what happened in real life. With movies that are “inspired” by true events, they have much greater creative freedom to fictionalize and sensationalize different aspects of the story.
The 1994 film “It Could Happen To You” is only very loosely inspired by the actual events.
“Ours is really a luck story, but the filmmakers turned it into a love story,” Penzo shared in an interview with Entertainment Weekly.
Except for the part about us winning, it’s totally fiction.
In the film, the pair are strangers. The cop, Charlie, suggests the lotto tip because he doesn’t have cash on hand. The waitress, Yvonne, agrees and they win a $4 million portion of a $64 million jackpot. Tensions arise when Charlie’s wife, Muriel, doesn’t want to give Yvonne her share. The couple ultimately divorce and Muriel successfully sues for the full lottery winnings, including what Yvonne was promised. In the end, the cop and waitress fall in love and get married. In the media storm following the divorce proceedings, they receive thousands of letters and donations from fans across the country, totalling more than $600,000. At the end of the film, the couple fly over Central Park in a hot air balloon.
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!”
