Players can either win by finding one of the ultra-rare game pieces such as the Vacuum, or by completing a set of properties by finding the extremely rare odd-one-out — the odds of finding Boardwalk, for example, are about one in 600 million.
As the head of security for Simon Marketing, the company responsible for running the promotion, Jacobsen was the man entrusted with transporting those pieces from the printing plant to the packaging factories, where they would be randomly attached to McDonald's cups and cartons.
He first stole a piece worth $US25,000 in 1989 "to see if I could do it", giving it to his brother-in-law at a family gathering. In 1995, believing the game was already being rigged to exclude Canada, he set his plan in motion.
While en-route to the chosen factory, Jacobsen would slip into the airport bathroom — the only place he could escape from the female auditor tasked with monitoring the process — take the winning pieces out of the envelope and replace them with "commons".
Knowing he could not cash them in himself, Jacobsen sold the pieces to people recruited through friends and family — some of whom mortgaged their houses in order to make a down-payment — ultimately redeeming more than $US24 million ($35 million).
Strip club owner Gennaro Colombo, who claimed to be connected to New York's Colombo crime family, was the man who would "industrialise" Jacobsen's Monopoly scam after a chance meeting at an airport.
Colombo, who even appeared in a McDonald's commercial waving a giant key after being slipped a winning game piece for a Dodge Viper, died in a car accident in 1998.
His wife Robin, who was driving at the time, believed it was her late husband's family who were behind the tip-off to the FBI in 2000 that ultimately brought down "Uncle Jerry". "That was their retaliation," she told The Daily Beast.
The tip-off sparked a year-long investigation dubbed operation "Final Answer" — after Who Wants to be a Millionaire? — that culminated in two FBI agents disguised as a McDonald's film crew descending on the home of one of Jacobsen's "winners".
McDonald's agreed to continue running the promotion even though it was aware of the fraud, with the FBI insisting it needed to catch the perpetrators red-handed.
In August 2001, eight people including Jacobsen were arrested in co-ordinated raids and charged with conspiracy to commit mail fraud. In total, 52 members of the conspiracy were ultimately indicted.
"The goal was to catch these guys red-handed, and that's what we did," a McDonald's spokesman told The Washington Post. "We hope Americans will see that we were innocent victims along with our customers, and we got scammed by a sophisticated web of crooks."
The FBI said the investigation "required the utilisation of some of the most sophisticated and innovative investigative techniques available and the assistance of FBI personnel in dozens of cities across the country".
Then US Attorney-General John Ashcroft said, "This fraud scheme denied McDonald's customers a fair and equal chance of winning. Those involved in this type of corruption will find out that breaking the law is no game."
In 2004, an appeals court threw out the convictions of four men involved in the scheme, finding "a complete failure of proof" on the conspiracy charge. The group had maintained they were not aware the winning tickets had been stolen.
McDonald's terminated its contract with Simon Marketing in 2001 and the two companies sued each other. McDonald's case was thrown out and the fast-food company later agreed to pay Simon Marketing a $US16.6 million settlement.
Former cocaine trafficker Andrew Glomb, one of the eight originally arrested in the FBI's sting operation, told The Daily Beast he wasn't angry about his conviction. "It was a game, and I lost," he said.
Glomb said he still spoke to Jacobsen, now 76 and living quietly in Georgia. "Every time I talk to Jacobson, I always tease him, I say, 'You got any tickets?'"
