The Supersized Scheme to Beat McDonald's Monopoly

When the annual McDonald's Monopoly comes to a close, your “big winnings” will likely amount to a free McFlurry—and that’s if you’re lucky. Logically, we know the odds of buying eligible menu items and collecting a full set of cash prize-winning pieces like Boardwalk and Park Place are infinitesimal. Still, we rip the game pieces from soda cups and fry boxes with the secret hope of receiving a coveted property.

And when we say the odds are bad, we mean they’re bad: According to Business Insider, you have a 1 in 602 million chance of getting Boardwalk, a 1 in 150 million chance of getting Short Line, and a 1 in 15 million chance of getting Kentucky Ave. Unless you’re someone like Jerome Jacobson. Then your odds improve substantially.

Jacobson worked in security at Simon Marketing Inc., the company responsible for the printing and distribution of McDonald’s Monopoly game pieces. After the pieces were printed, the valuable ones were placed in envelopes and given VIP transport to the various production plants where they were supposed to be attached to the McDonald's packaging, Priceonomics says. Jacobson, a former policeman, was the escort for these important pieces—and by 1989, two years into the Monopoly promotion, temptation proved too sweet to resist. He started out slow, opening an envelope and stealing a stamp worth just $25,000. He gave it to his stepbrother, who cashed it in without incident.

With one successful heist under his belt, Jacobson, who went by the alias “Uncle Jerry,” got bolder. By the mid-'90s, virtually all of the major prizes were awarded to someone who had been handpicked by Uncle Jerry. One donation suggests that he may have felt a little like Robin Hood: In 1995, St. Jude’s Hospital mysteriously received an unmarked envelope containing $1 million worth of winning pieces. Though the gift remained anonymous for years, it was later revealed that Jacobson had been behind the donation, according to CNN.

In 2000, one of the members of the scam tipped off the FBI, which in turn launched an investigation they deemed “Operation Final Answer.” (Don’t judge the feds for confusing their games—a Who Wants to Be a Millionaire-themed McDonald's promotion was also hacked by Jacobson.) Using methods such as wiretapping, phone records, and even tailing suspects to a secret meeting, The New York Times reported, the FBI was able to confirm that Uncle Jerry and his crew had taken in excess of $13 million in prizes. More than 50 people were indicted, and Jacobson himself went directly to jail without passing Go. Not only was he sentenced to three years and one month in federal prison, he also had to return the $1 million in kickbacks he received for doling out the prized pieces. Game over.