This Ex-Cop Rigged McDonald’s Monopoly Game…And WON for 12 Years

This Ex-Cop Rigged McDonald’s Monopoly Game…And WON for 12 Years
Image: Cultured Vipers

Conspiracy & Fraud

Image: Cultured Vipers

You’d never think to associate McDonald’s long-running Monopoly game with conspiracy and fraud, but on September 10, 2001, a trial would begin that would see over 50 people convicted of mail fraud and conspiracy. The scheme was orchestrated and carried out by ex-cop and the mastermind, Jerry Jacobson, who would end up defrauding McDonald’s out of over $24 million.

You won’t believe this story of desperation, betrayal and wild antics.

Launched in 1987

Image: Trip Advisor

Although the Mcdonald’s Monolopy game is a huge nationwide event today, it had a very small start back in 1987. The first year alone the game generated over $40 million in prizes and since then the game has only grown thanks to a spot-on advertising campaign. With the hope of winning some of the amazing cash prizes, millions of consumers flocked to the restaurant to fill up their board pieces.

However, there was one big problem…

A Waste of Time

Image: Marketwired

Unfortunately, no one was going to win, even those super-sizing their orders to maximize their pieces. Why? Well, it seemed McDonald’s system to keep things fair was actually rigged. While the odds were always steep, in reality, they were much worse. The true odds were 25,000 to zero and the winning pieces were in the control of one man, who cooked up a system (although a sloppy one) to decide where the winning pieces were distributed.

Jerry Jacobson

Image: Wild About Trial

All Jerry Jacobson ever wanted to be was a police officer and he eventually achieved that dream. Unfortunately, due to a neurological disorder, he had to leave the force and moved from Florida to Georgia with his wife. At first, he floated from job to job in order to make it financially, before he landed a position at the Dittler Brothers, a printing company where his wife worked as a security auditor.

Working His Way Up The Ladder

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Over the next year, Jacobson would work his way up the security chain within the company until eventually he was promoted to Head of Production at Simon Marketing who produced the Mcdonald’s Monopoly pieces. Fellow employees remembered Jacobson as running the department with an iron fist. He would even go as far as inspecting workers shoes to make sure they weren’t stealing game pieces.

The One Man With the Power

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When it came to instant-win pieces, there was only one man who had access and that was Jacobson. He oversaw the printing of the pieces and was one of the few people with access to the safe that kept the ones with the large prizes. And even though he had an auditor at his side at all times, somehow Jacobson devised a scheme to rip McDonald’s off for millions.

The Initial Scheme

Image: CBS Miami

At first, Jacobson wanted to see if he could get away with stealing one of the winning pieces and cashing it in. He stole a piece worth $25,000 and mailed it to his brother in Miami, FL in the summer of 1989. Why did Jacobson turn to crime? Well, he revealed in court documents he felt like he needed to prove to his brother he could do actually pull it off.

Pay to Win

Image: Daily Star

Of course, once wasn’t enough for Jacobson and he began to sell winning $10,000 pieces to people as a side business. Unfortunately, McDonald’s began to have a string of inside thefts which caused Jacobson to suspend his distribution of the pieces locally and overseas until 1995.

No Canadian Printing

Image: HuffPost Canada

With Jacobson once again managing the promotional Monopoly pieces, he soon became angered with Simon Marketing when they declined to allow winning prizes to be printed in Canada. The company claimed they wanted the business to stay in the United States, but Jacobson felt this was wrong and knew Canadians would soon begin to question why there were no winners in their country.

A Rigged System

Image: World Lifestyle

It didn’t take long for Jacobson to believe that the game was stacked against the consumer. This motivated him to go ahead with his next scheme. Even better, he accidentally was shipped a set of anti-tamper seals for the winning pieces. It looked like things were set to go.

Lifestyles of the Rich and Famous

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During his time at Simon Marketing, Jacobson began to live a life of luxury. He flew everywhere first class, wore expensive name-brand clothing and dined at places like Ruth Chris Steak House where he would charge all of his food to his expense account.

Although he was making a comfortable $70,000 per year…greed took hold and he wanted more.

An Odd Group of Friends

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As Jacobson expanded his scheme’s operations, he would end up accumulating an odd assortment of friends to work with. One was Gennaro Colombo, a nightclub owner and operator of a gambling ring. Jacobson would also develop connections within the mob and soon had a wide net of people from mobsters to psychics to drug traffickers.

Every Prize for 12 Years

Image: Business Insider

For the next 12 years, this strange group won almost every Monopoly prize from McDonald’s that totaled to millions of dollars and even a Dodge Viper. Of course, Jacobson did throw some family members a bone every so often and one distant relative received $45,000. However, all of the “winners” found themselves indebted to Jacobson.

Paying Upfront

Image: Reader’s Digest

In order to score a winning piece, those who took part in Jacobson’s scheme had to pay a percentage of their winnings up front. Therefore, if you wanted to win $1 million, you had to make a $50,000 cash installment to Jacobson. Some people went as far as to mortgage their homes to make these payments.

A Web of Lies

Image: YouTube

Jacobson’s web of winners extended throughout Florida and other areas in the south. Those who paid for a winning piece had to drive to another state to cash it in, usually pretending to have just found the piece on their fries or drink cup. However, McDonald’s soon began to realize there were an unusually high amount of winners in the state of Florida.

The FBI Tipped Off

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While Jacobson was able to carry out his scam with no issues from 1995 to 2000, someone chose to tip off the FBI that the recent $1 million winners may have obtained their piece illegally. This would soon be the beginning of the end for Jacobson and his extended network of “winners.”

Taking Things Seriously

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The FBI immediately launched an investigation into the operation, tapping Jacobson’s phone and soon discovering his scam was more widespread than they could have ever imagined. The McDonald’s executive committee wanted the investigation called off due to the bad PR it could spread, but they chose to move forward, quickly closing in on Jacobson and his network of oddball workers.



The FBI decided to pose as a new crew and interview one of the most recent million-dollar “winners.” During the interview, they noticed how nervous he was and believed him to be lying. After months of surveillance and monitoring Jacobson and his extensive network, the FBI finally had enough evidence to move forward with charges. Through a series of raids, they were able to arrest everyone involved.

Guilty on All Accounts

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Jacobson chose not to fight his charges in court and pleaded guilty. He was sentenced to 15 years in prison, while his other conspirators had to pay huge fines and spend a year in jail each. Jacobson ended up paying $12.5 million in fines and legal fees.

Mcdonald’s Paying for It

Image: Gracie’s Blog

After Jacobson’s trial, McDonald’s knew they had to make things right with their customers. They spent millions on retribution to people who had hoped to win the ever illusive Monopoly prize money and offered over $10 million to 55 random customers. They also paid out $15 million on a class-action settlement.

In the end, Jacobson still believes he was giving back to those who were trying to win a rigged game, but the moral of the story is…McDonald’s Monopoly game is a gamble and you should really one expect to win a free small fries.

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