Securing the game pieces often meant Jacobson had to personally carry them in a case shut with a tamper-proof seal. But in the mid-90s, Jacobson figured out a way to rig the popular game so that the most lucrative winning game pieces would almost always find their way to people he knew - people who then shared millions of dollars in winnings with him, according to federal officials who announced the arrests of Jacobson and seven of his associates in 2001. It was Jacobson's job to look after game pieces for McDonald's promotional events, making sure no employees pocketed any of the prizes themselves. In the 1990s, Simon made the game pieces used in McDonald's promotional contests, including the Monopoly and Who Wants to Be a Millionaire games, where customers could win up to $1 million in prizes just by buying items like french fries or a soda.
Jacobson, also known as 'Uncle Jerry,' was once director of security for Simon Marketing.