McDonald's Monopoly Is Back. Has Anyone Ever Won The Million Dollar Prize Before?

McDonald's Monopoly has returned after a decade spent missing in action. As it turns out, some players have won the top prize before — and most have really needed that money. For instance, one was homeless at the time of their win, while another was unemployed and living with his parents. The term "winning," however, can mean different things to different people, a fact demonstrated by one instance of massive fraud related to the game. Although there are financial scams that cause far more damage, this scandal, which was orchestrated by an unscrupulous security company executive, is notable for the amount of people and money involved in the theft.

When it was launched in 1987, the marketing for McDonald's Monopoly was handled by Simon Marketing Inc., where Jerome Jacobson was the head of security. Two years later, Jacobson devised a scheme to steal printed game pieces — his position gave him unfettered access to the game printers — and offer them to associates for a cut of their prize. By 1995, the Monopoly prize had graduated to seven-figure territory. Jacobson's scam also involved a mafia-connected associate named Jerry Colombo. Jacobson got sloppy, however, handing out too many winning tabs to people in too close proximity and earning the attention of the FBI. This culminated in his arrest and the arrest of some 50 other "winners." While not quite the biggest heist in American history, Jacobson and Colombo's $24 million fraud was certainly significant. 

According to the U.S. Department of Housing and Urban Development, about 23 out of every 10,000 Americans spent at least one night unhoused in 2024. This number includes both people living on the streets and people precariously sheltered in transitional housing or motels. In 2001, day laborer Patrick Collier had worked his way off the street on just $50 a day, and he was living out of a hotel with his fiancee, Sandi Fabian, and his mother. The hotel was located across the street from a McDonald's, where Collier and Fabian were having breakfast on the day of his much-needed win. While most of us can only hope to find a McDonald's Happy Meal toy worth a ton of money in the future, Collier did even better than that.

After the FBI uncovered Jerome Jacobson and Jerry Colombo's scam, McDonald's corporate executives, hoping to overcome negative optics affecting customer loyalty, decided to give away five grand prizes of a million dollars at random to lucky McDonald's customers. Collier became one of those lucky winners that fateful morning when he was handed a certificate by store employees; he didn't even have to actually play the game to win it. However, his win was still associated with the game, technically making Collier a million dollar prize winner.  

For Jon Kehoe, an unemployed millennial living at home with his parents, 2010 was a year of growth. The only winner of the top prize in the United States, Canada, or Puerto Rico, Kehoe was a former construction worker who used to earn nearly half of his annual prize earnings before his unceremonious lay-off — his McDonald's Monopoly earnings work out to $1 million divvied up over 20 years, or $50,000 per year. Down on both luck and money, Kehoe decided to treat himself to a McRib meal at his local McDonald's drive-thru. He couldn't have foreseen that this Mickey D's run would turn into a million dollar windfall.

Kehoe needed two specific Monopoly board pieces — a Boardwalk and Park Place tab — both of which he found on his drink cup. According to a McDonald's spokesperson quoted in the Milwaukee Journal Sentinel, Kehoe beat odds of "one in 3.1 billion" to win. However, a year after winning the top prize, he still hadn't moved out of his parent's house (although he did contribute to home improvement projects and a modest rent.) He also reduced his chances of ending up dead broke by sourcing good financial advice from professionals at his bank and credit union, as well as remaining frugal with his spending.