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The McDonald's Monopoly Game Was a Smash Hit. But the Man Behind It Was Siphoning $24 Million

The man tasked with the iconic game's safety was secretly gifting friends and family lavish prizes, all under the fast food chain's nose

By Mark Gray

For some McDonald's fans, the fast food chain's annual Monopoly promotion was a highlight
The game offered game pieces that could lead to prizes — some that were life-changing, like houses, cars and cruises
But a man entrusted to keep the game in check was actually hiding a secret
For more than a decade, the iconic McDonald’s Monopoly promotion was an annual cultural moment — but then a 'McFlurry' of scandals and oddities rocked the contest to its core.

The Monopoly promotion, which began in 1987 and took place in the fall, was a marketing success from the beginning, as customers would collect game pieces attached to various food and drink containers or in newspaper or magazine ads.

Those game pieces would reveal an instant prize or a game piece to be used on the paper Monopoly board, which could also trigger a prize. If someone acquired the correct combination of game pieces — Park Place and Boardwalk, for instance — a house, car, cruise or large cash prize may await. The odds of winning a big prize, however, were astronomical.

“It is hard to find things that are less likely to happen than winning one of the bigger prizes in the McDonald's Monopoly game,” Misha Brown said on a recent episode of his Wondery podcast, The Big Flop, which did a deep dive into the promotion.

Still, the yearly promotion was a boon for McDonald’s, as sales reportedly rose during the six weeks the game was in effect.

McDonalds Restaurant playplace
A McDonald's in Tennessee.
Getty
Unfortunately, what McDonald’s and its customers didn’t know was that the Monopoly game was being rigged by the man hired to keep it legitimate.

At the promotion’s inception, a well-regarded manufacturing company was hired to print game pieces, and a man named Jerome “Jerry” Jacobson, a former police officer and security director for the marketing company who initiated the game, was tasked with supervising the printing process and ensuring the game’s safety. As part of his job, Jacobson had access to the winning game pieces, which were stored in vaults, the New York Times reported.

Two years after the game began, Jacobson hatched a plan to steal a game piece worth $25,000, which he gifted to his stepbrother in exchange for a cut of the money, the HBO docu-series McMillion$ claimed in 2020.

“He knew I could keep my mouth shut,” Marvin Braun, Jacobson's stepbrother, said in the docu-series.

Despite the family connection, no red flags were raised, prompting Jacobson to repeat the act, this time gifting a $10,000 ticket to his butcher in exchange for a cut, the Times said.

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A McDonald's store is seen on October 30, 2023 in Austin, Texas.
In 1995, six years into Jacobson’s secret pilfering, McDonald’s upped the ante, announcing a $1 million prize. Jacobson stole not one, but two $1 million game pieces, even gifting one anonymously to St. Jude Children’s Research Hospital, he would later admit to prosecutors, according to the Daily Mail.

Soon after, and by happenstance, Jacobson met a man with alleged mafia connections at an airport and decided to partner with him in the scheme. Jacobson even gave his new partner, Jerry Colombo, a game piece for a Dodge Viper.

Eventually, Colombo’s family started "winning" large prizes, with Jacobson continuing to get a cut of the money, which he used to buy a large home, a car collection, land on a lake and several vacations, per The Big Flop.

In 2000, however, the Federal Bureau of Investigation received a tip about the shadiness happening within the game and noticed that three of the winners lived just a few miles from one of Jacobson’s homes, which would be a statistical anomaly — even an impossibility.

"In my world, you don’t believe in coincidences very much, and the chance of having numerous family members and relatives win the game was just astronomical,” federal prosecutor Mark Devereaux said in the McMillion$ docu-series.

The McDonald's logo is displayed at a McDonald's restaurant on July 22, 2024 in Burbank, California. McDonald’s is extending its $5 meal deal in most U.S. restaurants past its initial four-week offering with the fast-food icon saying the offer has driven customers back to its restaurants.
A McDonald's in California.
Mario Tama/Getty
The FBI wiretapped Jacobson’s phone and eventually arrested him in August of 2001 for conspiracy to commit mail fraud, per CNBC. More than 50 others were convicted in connection with Jacobson’s scheme, the Times said.

“This fraud scheme denied McDonald’s customers a fair and equal chance of winning,” then-U.S. Attorney General John Ashcroft said at the time at a press conference announcing the arrests.

Jacobson was eventually forced to pay $12.5 million in restitution and was sentenced to 37 months in prison after coming clean, admitting to stealing approximately 60 winning game pieces and defrauding the game of $24 million in cash and prizes. He told the judge he charged roughly $50,000 per sticker.

“I am deeply ashamed of what I have done,” he said in court.

Jacobson now lives in Georgia, according to the Daily Beast.

In 2018, The Hollywood Reporter said that 20th Century Fox and Ben Affleck and Matt Damon‘s Pearl Street Films bid $1 million for the rights to the Daily Beast's in-depth story on the crime.

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