As a young man, Jerry Jacobson worked as a police officer in Florida for about a year when he sustained a wrist injury. In 1980, Jacobson went on medical leave due to a neurological disorder, then moved to Georgia with his wife. After recovering enough to work, he floated between jobs for a while until his wife helped him get a job at Dittler Brothers, the specialty printing company where she was assigned as a security auditor.

Beginning in 1981, Jacobson worked his way up the ladder and eventually took charge of production for Simon Marketing, the company overseeing the production of the McDonald's Monopoly pieces.

According to some who worked with Jacobson, he was so stringent about security "he inspected workers' shoes to check they weren't stealing McDonald's game pieces." A truck driver who transported the game pieces told the Daily Beast that Jacobson had even required someone to go to the bathroom with the driver during company hauls.

Even though Jacobson kept a watchful eye over his employees, he was the one person who oversaw the printing of the pieces and knew the combination to the safe that protected the instant-win pieces. Despite having an independent auditor on his back at all times, Jacobson was able to eventually work out a scheme to rip off millions of dollars from his employer and McDonald's.