Scamfluencers - Jerry Jacobson: The Real Hamburglar | 201

Episode Date: February 16, 2026

Since its launch in 1987, McDonald’s Monopoly game has become a cultural obsession, with millions of people buying Big Macs and fries, convinced they might be one peel away from a million-dollar payday. But for nearly a decade, the jackpot was unwinnable. The man responsible for distributing the pieces, Jerry Jacobson, was quietly stealing them and selling them for profit. And like every Monopoly game, it eventually ended – only this time, when Jerry’s game was over, the house rules no longer protected him.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Sachi, how do you feel about contests? Because I do feel like you have an opinion. And also, have you ever won anything? I don't feel particularly lucky. And I don't think I've ever won a contest. Yeah, I also feel the same way. But I do look up to people who are like always entering contests. Because I guess the thing is, like, you will win eventually.

You should have to enter as many as you can. I admire any commitment to almost any bit. That's really true. Even if it's evil, I'm like, well, you try. I'm like, you committed to something and I can't do that. Yeah, I agree. Well, today, I'm going to tell you the crazy story of why one huge fast food contest promised customers winnings of fancy cars or millions of dollars, but no one ever won anything but

small fries and cheeseburgers, at least not legitimately. The system was rigged as hell, and there was one guy deciding who won and who lost, and he decided, we are losers. It's August 2001, and Amy Murray is standing outside a brick townhouse in Rhode Island holding a gigantic novelty check for a million dollars. Amy is 30 years old with shoulder-length blonde hair. She looks like she could have been a cheerleader in high school. Amy is here to present the check to a man named Michael Hoover,

who's basically won the lottery. Not the state lottery, though. Michael found a million-dollar game piece from McDonald's Monopoly. the wildly popular game where customers try to collect pieces on fast food items and in magazines to win prizes. Amy works for McDonald's and is in charge of publicity for promotional games like Monopoly. Part of her job involves interviewing big winners like Michael so the company can use their stories and commercials. But today's check presentation is different. Because the camera crew standing next to Amy isn't her usual team,

they are all undercover FBI agents. Amy is a part of a sting operation designed to take down a group of mafia-connected scammers who've been rigging the monopoly game. She's been sworn to secrecy about the investigation. She can't even tell her family or her coworkers, which has been stressful and isolating. Amy is nervous, but she wants to help. She wants to catch the cheaters and restore McDonald's good name. Her heart races as Michael opens a door and welcomes them inside. Michael is a white guy in his late 50s

with a wide face and a full head of silvery hair. Amy hands him the oversized check and asks him to explain, on camera, how he found the winning monopoly piece. And Michael's story is weirdly specific. He says he brought a copy of People Magazine to the beach, took a nap, and then dropped the magazine in the ocean. So he stopped at the grocery store on his way home

and bought another copy of people. And that copy is the one that has, the instant win game piece inside. It's a pretty remarkable story, and to get even more evidence of Michael lying on camera, one of the agents suggests he take them to the beach and show them where it all supposedly happened. Amy stands on the sand holding her high heels in one hand.

She watches as Michael flashes a huge grin and poses with the giant check. Then, out of nowhere, a drunk guy runs up and snatches the check. One of the FBI agents takes off after him and tackles him to the ground. Okay, Sarah, hold on a second. I have a couple of questions about this. One is that this seems like a lot of energy for the FBI too exact on just like some drunk guy. Two, I'm wondering if everybody in the story knows that you can't actually cash a novelty check.

So even if he steals it, it's like stealing a poster. Also, what are they bothering chasing him for this is a sting operation? It doesn't even matter. Listen, once you're in the FBI mindset, all you really can do is react, you know what I mean? Right, yeah, yeah. But the FBI won't be able to stop the other criminals as easily. Michael may be the one holding a million dollar check,

but he's not calling the shots. Neither are the other so-called winners. They're all downstream from the real players. Serious criminals who've been manipulating the monopoly game for years. Their mafia-style ring controls all of the winning pieces. Amy and a rag-tag crew of FBI agents are rolling the dice, hoping to find the Mr. Moneybags all the way at the top. From Wondery, I'm Sarah Hagi.

And I'm Sachi Cole. And this is scam influencers. Since it was first introduced in 1987, the McDonald's Monopoly game has been a huge hit. Millions of people have bought Big Macs and fries, dreaming of a million-dollar payday. But for nearly a decade, customers had zero chance of hitting the jackpot,

at least not honestly, because the man in charge of distributing winning pieces across North America, Jerry Jacobson, was stealing them and selling them for a profit. For years, he passed Go again and again collecting far more than $200 each time. But eventually, every monopoly game ends. And when this one did,

the House rules no longer applied. This is Jerry Jacobson. The Real Hamburger. It's 1987 and Jerry Jacobson is on watch in Atlanta. Jerry is the head of security for a printing company called Dittler Brothers, a firm that specializes in printing things that need to stay secure, like lottery tickets and postage stamps. He's in his mid-40s, and with his broad shoulders, dark brown hair and thick mustache,

he looks like exactly what he is, a former cop. And now, Jerry has a new project to police. Dittler Brothers recently won a major new contract. McDonald's is launching a new promotion, modeled after the Monopoly board game, and Dittler Brothers will be responsible for printing every single game piece. These are the pieces that will get stuck to soda cups,

burger wrappers, and fry containers across North America. There are two ways to win the game. One, get a matching set of properties like boardwalk and park place, just like the board game. Or you can peel off an instant win ticket. Most of the prizes are small, like a free Big Mac or a happy meal, but some winners get things like new cars, vacations,

and cash prizes up to a million dollars. It's a brilliant marketing strategy. The game is simple to play and the rules are easy to understand as almost everyone has played Monopoly at home. And like the board game, it taps into the very American fantasy that one lucky break can change your life. The game also encourages people to buy more menu items, driving up McDonald's sales by as much as 40%.

It's crazy to me that McDonald's would even need a board game to drive up sales, but I guess if there is any fast food company that I would believe would find a way to gamify eating fries, it is McDonald's. Yeah, of course. And I was eating it up. Okay. And Jerry is an instant winner because his, his job took on a lot more importance with this new contract. Jerry grew up as a sickly kid

with chronic allergies in Youngstown, Ohio. But for a few years in his early 20s, he managed to live out his dream of being a police officer. Jerry was a bit of a wildcard. He once consulted a psychic for help solving a murder case, but eventually, health issues led him to leave the force. Jerry's wife at the time, Marcia nursed him back to health. She also helped him land the job but Dittler brothers. Jerry, it's worth noting, has a thing for getting married. Marcia was his fourth wife. But Jerry's got a darker side. Not long after helping him get this new job, Martha leaves Jerry, allegedly after he became violent with her sons. Years later, she tells the filmmakers behind the HBO docu-series McMillians that Jerry threatened to shoot her.

Despite his personal issues, Jerry seems to thrive at work. He has an intense management style. Jerry oversees a team of about 30 people and seems to enjoy bossing them around. He writes them up for mistakes and frequently criticizes his female employee's outfits. Oh, Sarah, you know, I really appreciate episodes like these because right out of the gate, he sucks. And it's so clear he sucks and he's a supervillain and I hate him. I mean, listen, it's safe to say this new McDonald's contract supercharges Jerry's inner cop. For every round of monopoly, Dittler Brothers produces half a billion thumb-nish. sized game pieces. Jerry designs an elaborate security system to protect the most valuable ones.

High dollar pieces are cut out individually and sealed inside envelopes with tamper-proof metallic stickers. Then they are locked in a vault and secured with dual-entry combination locks. When Jerry delivers the pieces to their final destination, he carries them in a custom vests he designed to better hide them on his body. And he's always accompanied by an independent auditor. Jerry even checks his employee's shoes to make sure they aren't stealing game pieces. Jerry's vigilance annoys some of his employees, but it impresses the team at Simon Marketing, the company that helps design and oversee the Monopoly game for McDonald's.

In 1988, just a year after Monopoly launches, Simon Marketing poaches Jerry from Dittler Brothers. They put him in charge of security for the entire $500 million McDonald's Monopoly operation. For Jerry, this is a dream assignment. He's making six times more than he did as a police officer. He's flying first class to deliver the winning game pieces to McDonald's packaging factories around the United States and charging lavish meals to his expense account.

Jerry should be on top of the world. But it's not enough. He wants more. And this time, he's not going to wait his turn. It's 1989 and Jerry is with his family in Miami. He's been working on the McDonald's account for nearly two years. It's a good job, and he has some of the authority he's been seeking his whole life. But he can't stop thinking about the monopoly pieces.

Every day, he handles tickets worth millions of dollars in prizes, money that could change his life forever. So today, Jerry quietly slides something special to his stepbrother, a McDonald's monopoly piece worth $25,000. Even Jerry can't fully explain what made him go from cop to criminal. Later, he admits he might have been showing off. Jerry grew up feeling like he was in his stepbrother's shadow. He also says he just wanted to see if he could do it

to show that he could do something big even if it's also illegal. But there's also a practical reason to give the monopoly piece to his stepbrother. Jerry can't claim the winning piece himself. If he wants the money, he needs someone else to turn in the ticket. and then give him a cut of the winnings. Jerry's stepbrother mails a ticket an official prize claim form to McDonald's corporate headquarters.

And it works. He gets the $25,000, and he and Jerry split the cash. Jerry's amazed. Not just by the money, but how easy it was. This might be why he tries again with his butcher. The butcher knows about Jerry's job and says he wants to win the monopoly game.

He offers to pay $2,000. in exchange for a $10,000 winning piece. Jerry agrees, but he knows that if a lot of winners are connected to him, it will raise red flags. So he tells his butcher to have a friend cash in the ticket. It works, and once again, Jerry has some easy money. Well, you gotta give him this. He's pretty practical.

Yeah, I mean, it's not without complication. He isn't the only one taking advantage of the game. Around this time, a teenager working at a migdictor. McDonald's in Wisconsin gets arrested for stealing 3,000 game pieces. After that, the company changes their system. Winning pieces are now handed out directly to customers from a secure role at the counter. This removes Jerry's team from the process, at least for a few years. In 1995, McDonald's expands a Monopoly game, offering a $1 million prize for the first time.

They return to sticking game pieces onto food packaging and in magazine. ads, which brings him back under Jerry's purview. Then, fate steps in. A supplier accidentally mails Jerry a role of the high-security metallic anti-tamper seals used to protect the winning game pieces. Now, he has everything he needs to cover his tracks, and he starts scamming again. Here's how it works. When Jerry travels with the winning pieces, he's always accompanied by an independent auditor.

But the auditor is a woman, which means there's one place she can't find. follow him, the men's room. So Jerry goes into a stall and opens an envelope filled with thumbnail sized game pieces, one of which is a big winner. He replaces it with a pack of regular pieces and reseals the envelope using one of the metallic anti-tamper stickers. Then he pockets the winning piece for himself. Jerry picks up right where he left off. He gives his butcher a piece worth $200,000. The butcher promises to pay him for. $45,000 in return and says his sister will go to Maryland to cash it in. But sometime later, Jerry sees a McDonald's commercial.

The butcher is on TV bragging about his win. On top of that, he screws Jerry on the deal and only pays him $4,000. Jerry is furious, but he can't exactly go to the police. So he decides that from now on, he needs to get paid up front. And he makes sure his operation is more organized. You might even call it organized crime. That's right, Jerry links up with the mob. Specifically, the Colombo crime family,

which is one of the infamous five families in the New York City Mafia. Jerry gets connected to Gennaro Colombo, a beefy balding guy in his early 30s who looks like he could be an extra on the Sopranos. Does the mob have nothing better to do? It was always my understanding that they had things to do, but they don't have anything to do other than this? They got their fingers in a lot of different pies, okay? It's a lot of gabagool.

As Jerry later tells the story, he just happens to run into Gennaro at the Atlanta airport in 1995. According to Jerry, Gennaro says he's on his way to Atlantic City to gamble and shows Jerry a bag stacked with $100 bills. Jerry claims that Gennaro opened up about his connections and his experience running sports betting

and underground gambling rings. This is a pretty implausible story. And for what it's worth, Gennaro's brother, Frank, later says another family member learned about what Jerry was doing and brought it to the family. Then again, some have speculated

that the connection might have come through Jerry's stepbrother, who knew a lot of discrete guys in the New York manufacturing business. However, they actually meet, Jerry and Gennaro develop a good working relationship. Jerry has the pieces, and Gennaro has the connections and muscle.

Together, they're ready to supersize the scam. It's 1997, and Gloria Brown is in Jacksonville, Florida, talking on the phone with one of her most chaotic friends. Gloria is a 39-year-old single mom and former social worker with big glasses and shoulder-length black hair. She's had major struggles in her life, but she's proud of what she's accomplished. She has a modest house, and even a rental problem.

property. Gloria is chatting with her friend Robin, who's in her late 30s with black, curly hair, and cat-like eyes. Gloria is pleasantly surprised when Robin shares her news. She recently married a rich man named Janaro Colombo. They got engaged after knowing each other for two weeks. Sarah, how long would I have to date a literal mob boss before you would give me your blessing? I don't know. It depends on how much stuff he's buying me, to be honest. How much am I benefiting from this? Yeah, I would buy you something very nice with his credit card. I think I'd have to be like, listen, you know this can't go anywhere far, but let's milk it for now. Yeah. Shared priorities.

Well, soon after, Robin and Gennaro visit Jacksonville and have lunch with Gloria. But to Gloria, the vibes are off. Janaro does most of the talking and grills Gloria about her family, her job, and her assets. she and Robin barely get to catch up at all. Later, Robin tells Gloria that now that Janaro has met her, he wants to offer her an opportunity, the chance to win a million dollars. Robin is enthusiastic,

but Gloria's bullshit meter is going off the charts. Slowly, Robin gives her more details. She claims that the McDonald's Monopoly game is rigged. This actually pisses Gloria off. She plays a game with her son all the time, and now she feels like a sucker. But Gennaro tells Gloria that this is how the game really works. McDonald's can't afford to give away millions of dollars

so the winners are picked in advance in exchange for cash up front. Eventually, he tells Gloria that the McDonald's ticket is a rare, risk-free investment opportunity, so she should invest as much money as she can afford to, and she can start by mortgaging her house. If you are ever trying to play a game, through a fast food company and you have to mortgage your house to do it. You know, I don't think I needed to host this show for three years to know that that's probably not a good idea.

Oh yeah, totally. And at first, Gloria agrees. She turns on the offer. But then, Gennaro applies the screw. He tells her there's another investor who's ready to buy the ticket, so she needs to act fast. Gloria has a bad feeling about it. But she also wonders if this is her chance to see. secure financial stability for her family.

And then, Gloria finds out that Janaro is in the mob. And now that the mob is involved, Gloria feels like she's in too deep to say no. A few weeks later, she meets Janaro on the side of I-95 and hands over an envelope with $40,000 in cash. She feels like she just sold her soul to the devil. Then, the real work starts. Janaro tells Gloria to say she found the winning ticket on the back of a fry box while cleaning out her car.

He also has her memorize his cousin's address and phone number to make it look like she lives in South Carolina instead of Florida. He's worried that too many winners are coming from the same general area. Gloria even records an answering machine greeting for that number in case anyone calls to check. Finally, in the spring of 1997, Gloria drives to a Hilton Head McDonald's with Gennaro. Her stomach is in knots as she hands her game piece to the manager. When the manager confirms that her win is legit, the store as employees break out in cheers.

But Gloria can barely muster a smile. I can't imagine this feels gratifying at all. She's had to do so much work to get this. It's shrouded in mystery and bad acts for her. I mean, like, part of winning these things, the joy of it is like, it's random. And you just feel lucky that day. Yeah, exactly. It just can't feel good.

And the celebration doesn't last. back home in Jacksonville, Gloria realizes she's gotten the raw end of the deal. The winnings are paid out in installments of $50,000 a year, and she has to give Janaro half while paying taxes on the full amount. In the end, she's only taking home about $10,000 a year. When she factors in the higher mortgage payments from her refinancing, she's barely breaking even. Gloria's kicking herself for getting involved in this scheme. But Janari's Giro's role in the scam and his control over this part of Gloria's life is about to come to a tragic end. It's 1998, about a year after Gloria paid for a winning McDonald's monopoly piece.

Gloria isn't the only person Robin and Gennaro have recruited for the McDonald's scam. Robin brought in her brother-in-law and her own father. Gennaro even claims a prize himself. He wants to be an actor, so he's delighted to appear in a McDonald's Monopoly ad, flashing a wide grin and holding up a giant fake key to a bright red sports car. Gennaro might feel like a winner, but Robin is having a change of heart. At first, Robin thought being a mob wife would be fun. She was coming off of a series of unstable relationships,

and Gennaro's wealth offered security. They live with their young son, Frankie, in a lavish house in South Carolina, complete with a chauffeur and bodyguards. But Robin isn't happy. The excitement from their whirlwind romance has petered out and her husband is distracted. He's cheating on her with several women, including her personal trainer. And he's spending a lot of time on his new business venture, a strip club called The Fuzzy Bunny. When local officials try to shut it down, he turns a strip club into a church where people just happen to be stripping.

I know that that's wrong. I know. I think it's a flawless business model. Listen, I'm genuinely shocked they didn't do that in the Sopranos. It's crazy that they're not doing that everywhere across this fine country. Right now. Yes. Robin is feeling isolated and lonely,

so she starts confiding in an unlikely source, Jerry Jacobson. They know each other through Gennaro's work, and Robin sees Jerry as driven and successful. Even without the monopoly scam, Jerry is making the equivalent. of over $100,000 a year from his job at Simon Marketing, and the scam is only making him richer. Jerry has started dressing in sharpsuits, and he joined a classic car club.

Robin finds him sophisticated, and more importantly, he listens to her. They sometimes chat on Robin and Gennaro's home phone line. Jerry even half-jokingly proposes to her, but he also tells her she needs to make up with Gennaro. You know, I'm starting to think, think that Robin may not be a very good judge of character. Sarah? I mean, he's sending mixed signals, you know? And eventually, Robin has had enough. She tells Janaro she's going to leave him,

but he says divorce isn't an option, and he means it. After their discussion, Janaro makes sure Robin is always with him, one of his family members, or someone in his entourage. Robin feels trapped. Finally, she tells Gennaro she'll try and make it work on one condition. They have to leave South Carolina and start fresh elsewhere. In May 1998, Robin, Gennaro, and their son Frankie get in their Ford Explorer and head to Georgia looking for land to buy a new house. But they never make it. During the drive, they get into a terrible accident with a speeding F-150 truck.

First responders have to use the jaws of life to come. cut Robin and Frankie out of the car. Gianaro suffers serious injuries and dies in the hospital two weeks later. Robin is distraught. She's grieving her husband, but she's also worried the Colombo family will blame her for the accident since she was driving. They already aren't her biggest fans. She's not Italian, she chain smokes, and she has an outspoken personality.

She's not exactly the family's idea of a traditional wife. Robin also wants to keep her son, the first Colombo grandchild, away from the family business. This annoys her mother-in-law who's very possessive of the baby. On top of all of this, she doesn't have Janaro around to support her anymore. Robin is used to the lavish lifestyle of a mob wife and she doesn't want to get a regular 9-5. So she starts running a new scam, insurance and credit card fraud.

This is so unfortunate. This just feels like a woman who's been. backed into a corner and she has no idea how to take care of herself because she has always been taken care of by other people. And now she is going to dig herself even deeper in a hole. You are very correct, unfortunately. About a year after Gennaro's death, she gets caught and goes to prison. While she's locked up, Gennaro's mother gets custody of Frankie. Robin isn't the only person Gennaro left behind. Without his mob connection, Jerry now has to find new winners on his own, a situation that's about to create a McFlurry of problems.

When A.J. Glom first hears about the McDonald's Monopoly scam in 1998, he's excited. But it's not because he needs the money, it's because the con sounds like a real thrill. AJ lives in Fort Lauderdale. He's in his late 50s with a mustache, a prominent nose, and an easy laugh. And he's no stranger to breaking the law. He recently finished serving a 12-year sentence for trafficking cocaine. After he was convicted, instead of reporting to prison, he fled to Europe and spent 16 months as a fugitive

before finally being arrested in a San Diego donut shop. AJ has tons of stories from the 70s and 80s, from taking poppers with famous authors in Monte Carlo to hiding a gun and a bologna sandwich during a brief stint as a would-be hitman. And while he's trying to stay out of trouble since getting out of prison, his current life seems boring. So when a friend tells him about the McDonald's scam, A.J. feels a familiar rush. The same one he used to feel when he was on the lamb. He's in.

Well, you know, at least he's honest about what he needs and wants in this life. He is not pretending to be a good guy. He knows what he needs, and it is crime. I admire it. Soon enough, A.J. is holding a lot. holding a plastic baggie with a winning piece in it. To help Jerry spread winners out geographically, A.J agrees to cash in the ticket in Pittsburgh where his parents live. But then, A.J. thinks about how much publicity the winners got,

and he decides he doesn't need that kind of attention. So he proposes a new plan. He'll give the ticket to a friend in San Diego, and they'll split the winnings. Soon, A.J. becomes part of a web of recruiters doling out tickets for Jerry. Like Robin, he focuses on. trying to help people he knows, including a man he met in prison in West Virginia. For AJ, having the power to make someone rich, or at least less poor after paying taxes and their kickbacks to Jerry, is a huge rush.

They must also all feel some sense of power, too, in that they are scamming, like, one of the biggest companies in the world. Yeah. Like, the person that they're ripping off is McDonald's. That feels amazing. Yeah, I could definitely see. sense justifying this in like a Robin Hood style way. Yeah, exactly.

Eventually, AJ starts working directly with Jerry, who's pushing 60 now. And Jerry probably enjoys working with AJ, because, unlike some of the other winners and recruiters who can't resist going on TV to brag about their wins, AJ keeps a low profile. And this seems really important to Jerry. AJ notices he's becoming increasingly paranoid. His new wife, Linda, doesn't know anything about his criminal enterprise. Keeping this secret has turned Jerry's hair gray. I remember how he consulted psychics when he was a cop?

Well, he's back at it. At one point, he starts seeing a psychic-slash-chiropractor to help manage distress, and he pays with a $50,000 game piece. I mean, at that point, why not? He's just handing these things out like candy. Yeah, why not? And you know, what else did you pay a psychic slash chiropractor? If not, a game piece.

Yeah, legal tender? I'm not going to give them money. No. And over the course of two years, AJ recruits 10 winners for Jerry. By 2001, the scam has been running for more than a decade. Dozens of people are involved, and Jerry has stolen as many as 60 winning pieces, worth over $24 million in total. Jerry must think he's a real game match.

master, but someone else is about to spoil his good time. It's March 2001, about three years after AJ was brought into Jerry's operation, and Doug Matthews is bored at work. Doug is an FBI agent in Jacksonville, Florida, a sleepy field office that doesn't usually see a lot of big action. This is annoying for Doug because he's pretty ambitious. He's a 29-year-old newly minted agent with a boyish face, brown hair, and a young. a warm southern drawl. He looks like a grown-up frat boy or the bully from a Y2K-era teen movie.

He's also a class clown, constantly making jokes and looking for something goofy. So he gets really excited when he sees a post-it note on a veteran agent's desk that reads, McDonald's Monopoly fraud? Doug asks the agent, Richard Dent, what the note is about. Richard explains he got an anonymous tip claiming that the McDonald's Monopoly game is rigged. But it sounded so wild, he didn't take it seriously. Doug loves wild. This is exactly the kind of thing he's been looking for. So Richard gives him the green light to look into it.

Doug calls the tipster back. They give him three names, three million-dollar winners who all appear to be related. Doug starts digging into the case. If the tip is real, this is white-collar fraud on a massive scale. He convinces Richard to reach out to the U.S. Attorney's Office who are intrigued.

So the FBI sets up a meeting with McDonald's executives at the FBI office in Jacksonville. They're joined by Assistant U.S. attorney Mark Devereaux, who's in his early 40s with a neat mustache and silver hair. He's a snappy dresser, the kind of guy who will later wear a tuxedo to court to protest their growing trend of casual Fridays. This is a serious crime, but Doug doesn't quite match the vibe. He shows up to the meeting wearing a gold suit which horrifies his superiors. Sachi, can you read how he later described this decision in the HBO docu-series McMillians? Yeah, he said, quote, I had it in the closet and I thought this is a great opportunity to wear it. This is like a golden fry suit, right?

Unfortunately, I find this very funny. Yes, this is how you should treat this kind of crime. I agree, but I hate when a guy has a little bit like that. You're like, okay, I'm clapping now, baby. Oh, just enjoy the bit, Sarah. We live in hell. And I'm too deep in, you know, there's a lot going on here for me. During the meeting, the FBI is cagey.

They don't know yet if McDonald's is a victim, or if some of its executives are co-conspirators. They tell McDonald's the game is rigged. They just don't know exactly who is behind it. McDonald's is worried that news of the scam will leak and ruin the company's reputation. But the executives agreed to cooperate with the FBI, and crucially, to keep the game running so they can catch the fraudsters in the act. A few weeks after the initial tip, the FBI gets permission to run wiretaps

on some of the alleged collaborators. They discover a pattern. Several of the winners reference the same person, Jerry Jacobson. When the agents realize Jerry is the head of security for the company that distributes the game pieces, they become convinced he's involved, even if they aren't sure how.

They're making real progress. but Doug hates listening to all the phone calls, so he pitches another idea. What if they did an undercover operation? McDonald's is already doing publicity interviews with all of the winners, so why not use these interviews to collect evidence from people they suspect

are in on the fraud? A few weeks after he pitches the idea, Doug gets called into the FBI's top boss's office. He's nervous and worries he might be getting fired. Instead, they tell him, the fake interviews are a go. Doug might be a goofball, but he's just been handed

an undercover operation involving one of the most famous clowns in the world, Ronald McDonald, and it's about to end Jerry's winning streak. It's April 2001, and Amy Murray is sitting in a hotel room in Hilton Head, South Carolina. The room has been half-heartedly

turned into a cramped TV studio with dim lighting and a couple of chairs. Amy is the McDonald's communication manager from the beginning of the episode. And today, she's sitting next to an undercover FBI agent and interviewing Gloria Brown, Monopoly winner and Robin's friend. Amy is dedicated to McDonald's and sees this undercover operation as a way to catch the people who rigged the game and help salvage the company's reputation.

She feels a little bit bad about lying to people like Gloria who clearly doesn't want to be here. but Amy is a professional, so she keeps a smile on her face as Gloria struggles to recount the story of how she found her winning ticket. Then the team hands Gloria a photo. They tell her it's the McDonald's in Hilton Head where she supposedly cashed in her winning ticket and asked her to autograph it. And although a lot of McDonald's restaurants do look similar, Amy and the agent are pretty sure Gloria will recognize this one because it's in Jacksonville where she actually lives. But Gloria doesn't recognize it, and she signs the photo.

While these interviews with the winners are happening, Amy is also working on a new cycle of the Monopoly game. The FBI hopes it will help them catch more criminals. It sounds like this is entrapment if they're setting something up that they know is already flawed and broken. Like, is this allowed? I mean, Amy and her bosses know this is risky, running a game they know is compromised

could open McDonald's up to lawsuits, but they want to do the right thing. And to make it look legit, they go all in, complete with a huge advertising blitz. The game will run for four months, which gives Amy and the FBI a tight deadline to catch the criminals in the act.

Each time someone reports a win, Amy notifies the FBI and they schedule a visit to interview the winner. In August, they visit Michael Hoover, the guy photographed holding a giant check on a Rhode Island beach. By the end of the month, after four months of interviews, wiretaps and surveillance, the FBI has what it needs. They know Jerry Jacobson is at the center of the fraud ring and that he's working with several recruiters,

including A.J. Glam. They still don't fully understand how Jerry is stealing the game pieces, but they have enough to make arrests. For years, Jerry has been conning McDonald's. but soon he'll be the one to grimace. It's a warm Monday morning in August of 2001, and John Boyanowski arrives at work to find a thick stack of paper sitting on his chair. John is in his 20s with brown hair and a boyish face,

and he's a cub reporter for the Greenville News in Greenville, South Carolina. The 38-page report came through the office fax machine over the weekend, and as John sips his coffee, he realizes, this isn't a normal police report. It's a top secret FBI memo, and it details an upcoming massive bust tied to a fraud ring involving the world's largest fast food chain.

The Greenville News is a small local paper, so John assumes a lot of reporters got the same facts. Plus, it's already been a few days since the facts came in, but when he checks the headlines, he can't find the story anywhere. This could be a major scoop, so John calls the FBI office

in Jacksonville for comment, explaining he thinks they may have faxed him something by a mistake. Idiot. I hope the cop who took his number was the one who accidentally sent him the paperwork. This is the story of a lifetime. I dream for such things to happen. Listen, he's young so he doesn't understand. Do not go to the cops and say, I think you sent me something mistakenly. I think you made a boo-boo.

Take it. Yeah, hey. Take the gift. I know you guys are the state. I just want to see if I can help you. Insane. Well, the reaction confirms that this is indeed a real story. The FBI is shocked.

And that same day, agents fly to Greenville to meet with John and his editors. They ask the paper to hold off on publishing the story. John and his editors agree in exchange for an exclusive once the raid happens. During the meeting, John asks how the memo was sent to their report. newsroom. The FBI agents won't say, but Sachi, would it shock you to hear that everyone in their office suspects it was Doug? For what it's worth, apparently there was a legitimate glitch with the FBI's office speed dial. A week later, John wakes up before dawn and climbs into a black SUV with FBI agents. They hand him special headphones so he can listen in on the raid as it

unfolds. John hears agents pound on the door of Jerry's home in Georgia. and take him away in handcuffs. The agent sees Jerry's sports car, along with a trash bag of cash they find in the trunk. He listens as the FBI arrest seven of Jerry's co-conspirators, including Michael, who has picked up mid-massage at a hotel spa in Wisconsin, still wearing his bathrobe and slippers.

Gloria is arrested as she's making breakfast in Jacksonville, and AJ is taking into custody while reading the paper at his house in Fort Lauderdale. Meanwhile, Robin, who's still serving time for credit card fraud, gets a visit from the FBI in prison. Oh, that must be a really comforting visit. I mean, she's already in prison, you know? I get, yeah, I mean, I wonder if her thought process is like,

could it get worse, I'm already here. Well, the FBI charges Jerry, A.J. Robin, and the winners with conspiracy to commit mail fraud because every winning piece had to be mailed to McDonald's headquarters. John breaks the story in the Greenville News and the case becomes a media sensation. Attorney General John Ashcroft goes on TV announcing somberly, quote, Those involved in this type of corruption will find out that breaking the law is no game. Jerry is all over the headlines and he's about to go on trial.

But the FBI is about to have much bigger problems. I feel like a legend. It's about two and a half weeks after the raid, and U.S. attorney Mark Devereaux is standing in a packed U.S. District courtroom in Jacksonville. Mark is there to indict the people involved in the McDonald's fraud case. Jerry is also being arraigned. Reporters are there scribbling notes about one of the splashes stories in the country. Then, everything stops.

Because the next morning is September 11, 2001. Suddenly, a fast food fraud case doesn't seem like such a big deal. And the Jacksonville FBI office comes under fire because three of the 9-11 hijackers had spent time in the area a year earlier. One of the agents says that if the Bureau hadn't been so focused on the McDonald's case, maybe they could have stopped 9-11 from happening. It's interesting that this sort of ends with 9-11 because the story and this case does feel so pre-9-11.

Like it speaks to a version of the world where you could bring a full tube of toothpaste on a flight. It's as if the FBI had nothing better to do. It's a lot of resources for a fast food game scam. Of course, it's like creating a fake publicity team. I mean, there's just so much that went into this. And the monopoly scam, understandably, falls out of the headlines. Over the next few months, the FBI indicts more people. Eventually, more than 50 are charged in the scam.

Many of them, including Gloria, plead guilty. Seven months later, Jerry does as well and agrees to testify in the government's case. In August 2002, Mark goes back to court, this time with Jerry as his star witness. Doug Matthews shows up to court in his gold suit, the same one he wore to the FBI's first meeting with McDonald's. Mark tells Doug he's making a mockery of the justice system and that he'll alienate the jury. He demands that Doug Go change. Yeah. You already made the joke once, bro.

Yeah, I'll say this. That might be a joke that would work on me once or twice or three times, but I think for the general population, and namely a jury, best not to do bits. Yes. If he was truly about that, he could have figured out a different bit. Just get a different suit. You can't figure out a hamburger suit grow up.

Well, when Jerry finally takes a stand, He admits to stealing up to 60 game pieces worth over $24 million and says that DeFraude McDonald's was the biggest mistake of his life. Jerry tries to get a lighter sentence by pointing out his one act of charity, sending a million-dollar game piece to St. Jude's Children Hospital. Mark isn't impressed with Jerry's Robin Hood Act. He argues that Jerry gave the piece away at the last minute because he hadn't lined up a buyer before the contest deadline.

Jerry tries one last move. He hands the FBI documents that he says prove that Simon Marketing deliberately rigged the game to prevent Canadians from winning major prizes. But Mark doesn't buy it. He tells a courtroom that the FBI looked into this and found no evidence of wrongdoing by McDonald's or Simon Marketing. I mean, of course he's going to dismiss any Canadian evidence, as you and I know, our inferiority complex grows. Every day. Yeah, it's like, who cares? Oh, no, Canadians couldn't win.

That's okay. No one's looking north of Montana. Of course. And in January 2003, Jerry is sentenced to more than three years in prison. AJ gets a year and a day. Some of the defendants were placed under house arrest, while others were fined and put on probation. Afterward, Mark moves on to his next big case. But for the people pulled into Jerry's orbit,

it will take decades to pick up the pieces. It's 2020, nearly 25 years after Gloria walked into a Hilton Head McDonald's to claim her fraudulent prize. Now, she's at her home in Jacksonville, getting ready to tell her side of the story. Gloria is talking to a film crew, a real one this time. They're working on an HBO docu-series called McMillions based on reporting by journalist Jeff Mesh. But this time, she's telling her story on her own terms. Gloria tells the filmmakers how scared she felt dealing with Gennaro and how little money she actually walked away with.

She says that, like many of the other people involved in the scam, she was just trying to claim a piece of the American dream. Here's Gloria. I just wanted to do better in life and didn't think of all the repercussions that was involved. I did a crooked deed and I've been knocked down. Just get up and keep moving. And that's what I did.

The filmmakers also check in with another person who's been deeply affected by the McDonald's scam, Robin and Gennaro's son Frankie. He was only a toddler when his father died, and he's in his 20s now. Frankie talks about how traumatizing it was when his grandmother, Gennaro's mom, Ma Colombo, showed him a picture of the wreckage when he was just nine years old. And it turns out, Frankie actually played a big role in bringing down the scam. At the end of the documentary, Gennaro's sister-in-law claims that Ma Colombo was the one who tipped off the FBI. She says Ma wanted to make sure Robin stayed in prison

so that Frankie would stay with his grandmother. There's some evidence to support this claim. All three fake winners in the original tip were connected to Robin. For what it's worth, Robin believes this is true. I kind of believe it's true. That feels really believable. Pretty crazy thing to do.

Oh, banana. For sure, but I guess it feels like who else would have been able to take him down if not somebody who knew enough. Yeah, for sure. But today, Frankie says his mom and his grandmother have mended fences. In the documentary, Robin and Ma Colombo actually embrace on camera at a family gathering, their friends and talk all the time. According to The Daily Beast, Jerry is still married to his seventh wife, Linda. He has a monthly restitution payment of around $370.

Amy continued to work at McDonald's for another two decades and retired in 2023 after becoming a vice president of global marketing. McDonald's publicly apologized for the fraud and continued to run the monopoly promotion until 2015. The company relaunched the game in October 2025 after a decade-long hiatus, this time using the McDonald's app to collect game pieces and redeem prizes. This is a weird one. it really just started from like a very, how do I say, like a very honest, dishonest place. It's really straightforward. Yes, it's pretty interesting that Jerry was so proud of how good he was at his job that he was like, it isn't enough.

Not only am I good at this, like I can subvert it because I am the best at this. But overall, it just seems like I know there were millions of dollars stolen, but with the work of finding someone new, having them claim it, them getting taxed, all that kind of stuff. It just seems like so many steps, you know, was it worth it in the end? I don't think so. No, it wasn't worth it because it was like obvious that they were going to get caught. I mean, like the mistake that they made was that all of the winning seemed too tied closely to the guy who started the scam.

Hindsight is 2020. But if he just scaled it down a bit and kind of stole the winning tickets every few years, got to know, someone knew who wouldn't be tied to him, I do think he could have gotten away with it. I mean, he absolutely could have because if it wasn't for Janaro's mom, who would have tipped it off, you know? Yeah, another scam where we look around and realize if you had just been a little bit happier with a little bit less, you probably would still be doing this. I'm surprised, personally, the biggest shock is that there weren't more murders and violence involved in this. Yeah, it's a cleaner scam than you would think. Weirdly not violent the way I would have expected.

Yeah, everybody just sort of went down pretty easily. Does this make you want to go get some fries with me? You know, I will say this did make me hungry for fast food, but it really pissed me off because it's like, I don't know, I think all of it is a scam. Where what you're making me buy more McDonald's so I can maybe win something. Yeah, of course. I don't view like McDonald's as a victim here. I will never view them as a victim of anything.

I guess there are people who thought that they had a fair shot and bought, you know, McDonald's food thinking that they might win something. But I don't know. I think if you're playing any lottery, you get what you get. And what you get usually is a loss. There were people who like went crazy getting these pieces trying to get the whole board or whatever and all that. And like knowing that they were toiling away only to not. really ever have a chance at winning anything good must have just been so insane to the point

where I'm like I'm surprised at one of these obsessive McDonald's Monopoly players and weren't like, hey guys, has anyone noticed that like none of us win? Yeah, I guess the McDonald's Monopoly benefited from the fact that like people are used to losing in a lottery setting. Yeah. And especially because McDonald's is still like showing you like, look, these people have won. Somebody was winning them. It's not like, you know, a Willy Wonka ticket situation where they've put five and everyone's waiting for the fifth ticket to be called. You know, like that's how these things are framed. Most people lose the lottery.

I guess what's also interesting about this scam is Jerry figured out a way to make it two scams because there is like an MLM portion of this where he is sort of controlling how the money trickles. He gets paid the most. he controls who gets what. It's not just that he was stealing from McDonald's or stealing from the game and changing the odds, but that he's redistributing the wealth as he sees fit. Downline. Like he had recruiters and he had a downline

and there was like a flow to the money and to the fraud. Yeah, I mean, he wanted to be the boss of everything. If Jerry didn't do this, there could have been maybe world peace, I don't know. From your mouth to God's ears, yes. The lesson for me here is that there's never going to be a game a corporation puts on that you can ever win. There's no such thing as winning money this way. Now we have Mr. Beast and all these people making people do crazy shit for money.

You're not really getting anything. There's no universe where you're going to play a game and actually win something. And I think everyone should remember that. No company wants you to win something for free. So remember that the next time you supersize it. This is Jerry Jacobson, the real hamburgler. I'm Sarah Hagee. And I'm Sachi Cole.

If you have a tip for us on a story that you think we should cover, please email us at scampillincers at Wendry.com. We use many sources in our research. A few that were particularly helpful were how an ex-pop rigged McDonald's Monopoly Game and stole millions by Jeff Mage for The Daily Beast, the documentary miniseries, McMillians by James Lee Hernandez and Brian Lazzarte for HBO, along with their book, McMillians, the absolutely true story of how an unlikely pair of FBI agents brought down the most

supersized fraud in fast food history. Gloria Brown's book, I thought I would be living my best life, and Robin Colombo's book, from being a mafia widow to God's child. Susie Armitage wrote this episode, additional writing by us, Satchie Cole and Sarah Hagee. Eric Thurm is our story editor, fact-checking by Gabrielle Droulet, sound design by James Bray. Morgan. Additional audio assistance provided by Augustine Lim. Our music supervisor is Scott Velasquez for Frieson Singh. Our managing producer is Desi Blaylock. Janine Cornelow and Stephanie Jenz are our development producers. Our associate producer is Charlotte Miller. Our senior producers are Sarah Eni and Ginny Bloom. Our executive producers are Jenny Lauer Beckman and Marshall Louie for

Wondery.