How One Man With Mafia Ties Swindled $24M From McDonald’s Monopoly Game

July 28, 2021

By Aara Ramesh

Next month marks 20 years since the Federal Bureau of Investigations (FBI) conducted a series of raids and arrested eight individuals for a racketeering plot in which they defrauded McDonald’s Corp of $24 million dollars over a 12-year period. 

On the face of it, this summary may seem bland and unexciting, but the truth is that even Hollywood couldn’t spin a story quite like this. This tale has it all: wire fraud, mail fraud, money laundering, the New York mafia, convicted drug dealers, unscrupulous characters aplenty, roadside meetings to exchange cash, a gold suit, sting operations, clandestine airport bathroom operations, and more.

No one could blame you if you missed the story of Operation Final Answer (as the FBI nicknamed it), as the long-anticipated trial for it began the day before 9/11. The case came back into prominence in 2018, when the Daily Beast published a tell-all expose of the case, and in 2020, when HBO released a six-part documentary, “McMillion$,” chronicling the case.

In today’s piece we take you through the myriad twists and turns of this conspiracy, which, at times, truly beggar belief.

The Plot

The overall skeleton of the scam, which began as early as 1995, is at once both intricate and painfully simple, and is predicated on a series of extremely fortunate coincidences — if just one tiny detail had been different, the whole thing would never have happened at all.

At the center of it is a man called Jerome P. Jacobson, also known as “Uncle Jerry” (an affectionate moniker bestowed on him by a mob associate who we will get to later). At the time, Jacobson worked as the Director of Security at Simon Marketing, a firm that was contracted by McDonald’s to run a promotional scheme in the 1980s and 1990s that featured the board game Monopoly.

The twice-a-year game involved customers buying McDonald’s products and peeling back a sticker on the packaging to reveal what prize they had won. The rewards ranged from a free menu item to a $1 million jackpot. The odds of winning the jackpot were one in 250 million, and the odds of even just three connected people winning the same $1 million prize were “virtually impossible.”

As part of his job, Jacobson oversaw the printing of unique game pieces and was responsible for ensuring their safety and for hand-delivering them to the various McDonald’s packaging plants across the country. By chance, a supplier accidentally sent him a package of the holographic, tamper-proof stickers that were used to seal the envelopes that carried the game pieces. If the envelopes were ever opened after the pieces had been deposited inside, the seal would ideally reflect that. This delivery proved to be the true jackpot for Jacobson.

He concocted a plan in which he would break the seal, swap out the high-value tickets for lower prizes, and then just replace the seal. Where did he do this? In various airport bathrooms. Jacobson was accompanied on all trips by an independent auditor, who was supposed to double-check that the seal was in place. But Jacobson was able to make the swap by slipping her and doing the deed in the men’s bathroom, where she obviously couldn’t follow him.

Once he had the jackpot tickets, Jacobson would sell them to his family and friends for a premium, as he was not able to redeem them himself. As time went on, he recruited middlemen to do the sales for him, to make more money himself and to diversify the winners’ pool and make it less obvious that all of them were linked by a common person or geography. At his trial, Jacobson admitted to stealing up to 60 of the lucrative game pieces.

One time, Jacobson even anonymously “donated” a $1 million game piece to St. Jude Children’s Research Hospital in Tennessee, allegedly to offset the gravity of his crime in the eventuality he was ever caught. The extremely generous good-will gesture from a stranger even made national headlines.

So who were his co-conspirators?

The Cast

Each character in this plot is more colorful and vibrant than the last. 

Jacobson himself was briefly a police officer in Hollywood, Florida, before he went into private security. His then-wife was a security auditor and managed to get him a job with Dittler Brothers, a printer business known for serving high-profile clients with a need for extreme confidentiality. One of those clients was Simon Marketing, who devised and ran the Monopoly game for McDonald’s.

The first associate Jacobson recruited was Gennaro Colombo (also known as Jerry), who claimed to be a member of New York’s Colombo crime family. His father, Joseph Colombo, was apparently the head of that family. An attempted assassination on Joseph in 1971 was at the center of the Robert De Niro movie “The Irishman.” Jerry Colombo’s wife, Ruby, was also implicated in the scam, and roped some of her friends into it. 

Colombo died in a car crash in 1998, after which Andrew Glomb was brought on board. He was an ex-convict who had been imprisoned for trafficking cocaine on an airplane. Dwight Baker, a Mormon real-estate developer, was also drawn in after he grievously injured his spine in a tractor accident. He and his wife were hoping to make some money by selling the stolen pieces to pay off back taxes they owed.

These men would coach the winners through the process of lying to McDonald’s and claiming the money, even going so far as to falsify addresses in their name to legitimize wins and spread the victor pool out evenly.

In addition to these, a wide array of people benefitted from the scheme. One man who Glomb sold a ticket to was convicted in 1999 for dealing 400 lbs of cocaine. Another person used his winnings to buy a boat, which he then named… “Ruthless Scoundrel.” (You can’t make this stuff up.) Jacobson’s stepbrother, nephew, and butcher all benefited as well, the latter two trading $45,000 for game pieces worth $200,000. In a side-of-the-highway deal, Colombo sold Gloria Brown a $1 million ticket for $40,000 in cash, which she mortgaged her house to obtain.

In the end, over 50 people were convicted in the scheme, with the following ones arrested in August 2001 by the FBI:

  • Linda L. Baker, 49;
  • Noah D. “Dwight” Baker, 49;
  • John F. Davis, 44;
  • Andrew M. Glomb, 58;
  • Michael L. Hoover, 56;
  • Ronald E. Hughey, 56;
  • Jerome P. Jacobson, 58; and
  • Brenda S. Phenis, 50.

The Climax

The truth is that had it not been for one aggrieved party (the identity of whom is not definitively known), this case might never have even popped up on the FBI’s radar. In March 2000, someone left an anonymous tip directing authorities to an “Uncle Jerry” and highlighting that there had been a suspicious amount of winners in the Jacksonville, Florida area.

The local branch of the FBI picked up the case, led by Special Agent Richard Dent and his rookie partner Doug Matthews. They settled on the codename “Operation Final Answer” as a nod to the game show “Who Wants to Be a Millionaire,” which was co-sponsoring that year’s McDonald’s Monopoly contest. One actual suggestion initially floated was “Operation Hamburglar.”

To gain traction in the investigation, the team had to inform some executives of McDonald’s about what they had discovered. They also hoped to gauge whether anyone on the inside of the fast food company was involved in the scheme. Eventually, they roped in Amy Murray, then with the company’s marketing team, to work alongside them. At one point, the team encompassed 25 agents nationwide.

In a bid to get results and expedite the process, the FBI tapped suspects’ phones and deployed undercover agents as a production crew in a string operation to get on tape the suspects’ stories. In the end, Dent convinced McDonald’s to run the Monopoly game one more time, despite the fact that doing so would open the company up to future litigation, as they knowingly ran a compromised contest.

Finally, in August 2001, the Department of Justice (DOJ) and FBI had all the evidence they needed to successfully prosecute. In a cross-state, coordinated series of raids, the eight individuals named above were arrested. They were accused of conspiring to defraud McDonald’s and its customers.

Jacobson was also charged with conspiracy to commit mail fraud, a technicality that allowed him to be prosecuted, as it was not explicitly against the law or the game rules to sell a ticket onto someone else. The fact that he used the U.S. postal service to do it, however, is what got him in real legal trouble.


Jacobson, as the ringleader and mastermind, ultimately served just over three years in prison. He was ordered to pay $12.5 million in restitution, which the HBO documentary says he is still doing today. In his seventies now, he reportedly still lives in Georgia with his new wife. He has not appeared to have acquiesced to any interview requests since his arrest and conviction.

The remaining conspirators received varying sanctions and sentences for their involvement, though Glomb declares in the documentary that he would do it all again “tomorrow” if given the chance.

McDonald’s was noted to have cooperated with the authorities and was not implicated in the conspiracy, given that an external vendor had employed Jacobson. It tried, over the next few years, to gain back favor with customers by conducting instant million-dollar giveaways, to a mostly lukewarm response.

McDonald’s and Simon Marketing sued each other later in 2001 for breach of contract. That ended with the former agreeing to a $16.6 million settlement in favor of the latter. McMillion$ says that in the aftermath, tainted by the whole sordid business, both Dittler Brothers and Simon Marketing folded, resulting in job losses for many.

Roll Credits

The last time McDonald’s ran the Monopoly competition in the U.S. was in 2016. It still has similar marketing schemes in other countries, though it says it has created an “independent promotions task force” to monitor the administration of the games and ensure that a similar scam is not repeated.

Many argued that this was a victimless crime, really. McDonald’s would have paid out the money anyway, they say. And yes, some of the co-conspirators were intimidated or bullied, and there was an element of organized crime to the whole thing, but at the end of the day, critics point out, the “winners” chose to participate in a scheme that seemed fishy at best. Despite all the bend-over-backwards lies and reassurances of legality that the middlemen made, the “victors” should have known better, according to some.

It seems completely implausible, really, that but for one anonymous tip on a post-it noticed by a newbie FBI agent seeking excitement and adventure, Uncle Jerry could have gotten away with “stealing” $24 million.

The only victims in this case might be those poor customers who thought they had a fair shot at winning a million dollars. If it hadn’t been for that mistaken delivery of holographic stickers…