Presenting... American Criminal: The Great McDonald's Monopoly Heist

Summary

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Podcast Summary

Cautionary Tales with Tim Harford (Pushkin Industries)

Episode: Presenting... American Criminal: The Great McDonald's Monopoly Heist

Date: February 17, 2026
Featured Series: American Criminal, Episode One: The Great McDonald's Monopoly Heist

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Overview:

This episode of Cautionary Tales, hosted by Tim Harford, features an episode of the true crime history podcast American Criminal, hosted by Jeremy Schwartz. The story dives into the infamous McDonald’s Monopoly promotion—once a flagship marketing campaign of the fast food giant—and the astonishing, real-life heist that rigged it for over a decade. Exploring themes of greed, fraud, innovation, and corruption, the episode chronicles how one man compromised a billion-dollar campaign and unravels the dark side of an all-American dream.

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Key Discussion Points and Insights

1. Setting the Scene: Ordinary People, Big Temptations

• Gloria Brown's Choice (03:01)
  • Story opens in 1997 Charleston, where Gloria, a struggling single mom, is invited to dinner by her friend Robin and Robin's husband, Jerry.
  • After dinner, Robin proposes Gloria “win” the McDonald's Monopoly game, hinting at inside access to million-dollar prizes.
  • Gloria is skeptical but tempted:

    "She's not even sure if she believes what Robin just told her, but she really wants to. A million dollars. She can't even picture that much money." (04:32, Jeremy Schwartz)

2. Monopoly’s Origins: A Game About Unfairness

• History Repeats (06:25)
  • Explores the invention of the original Monopoly game by Lizzie McGee, intended as a lesson about economic inequality.
  • McGee's creation was appropriated by Charles Darrow, who profited while erasing her contribution.
  • Parallels drawn between the rigged game and how life (and business) frequently “isn’t fair”—foreshadowing the Monopoly heist.
    • "Lizzie did everything right... Then when someone violated her patent, she negotiated in good faith and she still got screwed." (07:50, Jeremy Schwartz)

3. The Rise of McDonald’s and Gamification

• Happy Meals to Monopoly (10:35)

  • Chronicles the evolution of McDonald's from a simple barbecue joint to a global juggernaut.
  • Happy Meals revolutionize family dining; soon after, gamified promotions such as Monopoly further spike sales and customer excitement.

    “It’s a shining example of American capitalism.” (13:35, Jeremy Schwartz)

• Monopoly at McDonald's (15:20)

  • Starting in 1987, McDonald's teams with Simon Marketing to produce the first Monopoly campaign.
  • Customers collect game pieces for prizes, ranging from fries to $1,000,000. Odds for the highest prizes are minuscule.
  • Simon Marketing runs all logistics—McDonald’s is hands-off with the nitty-gritty.

4. Anatomy of the Heist: Meet Jerry Jacobson

• Jerry’s Backstory (22:26)

  • Jerome “Jerry” Jacobson starts on the police force, faces health issues, and eventually lands a job at a printing company contracted to make McDonald’s game pieces.
  • Jerry is trusted with tight security, which only increases his desire for control and respect.
    • "He likes the respect it gives him, the feeling of control he has keeping a handle on the firm's production of high value pieces of paper." (27:25, Jeremy Schwartz)

• Jerry, The Security Zealot (28:00–30:00)

  • Implemented strict anti-theft measures (checking shoes, no solo bathroom trips) and became known as a stickler.
  • Eventually promoted to Head of Security at Simon Marketing.

• The Opportunity and the Temptation (31:55, 37:10)

  • A misdelivered box of holographic security stickers removes a key safeguard—Jerry now has everything needed to steal winning pieces.
  • Story told of a McDonald’s executive allegedly overruling the randomization of winners, nudging Jerry toward rationalizing his future crimes:
    • “They don't want any of the big winners going to Canada ever again... This is Jerry's version of events, and there's no public evidence backing up his story.” (39:33, Jeremy Schwartz)

• How the Scheme Worked (37:10–43:20)

  • Jerry initially tests the waters by giving a $25,000 winning game piece to his stepbrother; they cash it without trouble.
  • Sells other prize pieces to distant connections, always careful to avoid direct ties.

5. The Scam Evolves

• Perfecting the Theft (40:50, 41:45)

  • Jerry figures out the combination to the supposedly doubly-locked briefcase, allowing him to access envelopes of high-value winners.
  • Uses bathroom breaks as a cover to swap legitimate winning pieces with “duds.”

• Cautious Expansion and the Human Warning (44:45)

  • Jerry tries to bring others in, but some—like his stepbrother—refuse and urge him to quit:

    “Right in front of Jerry, Marvin walks over to a toilet, opens the lid and drops the piece in. Then flush.” (45:39, Jeremy Schwartz)

  • Jerry promises to stop, but in reality, he’s just getting started.

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Notable Quotes & Memorable Moments

• On the Unfairness of the Original Monopoly

  • “The point I'm trying to make is that life isn't always fair. Lizzie did everything right. She created something new... she still got screwed.” (07:50, Jeremy Schwartz)

• Jerry’s Rationalization

  • “McDonald's executives order Jerry to run the program again. They don't want any of the big winners going to Canada ever again... This is Jerry's version of events, and there's no public evidence backing up his story. But he'll later point to this as his reason for doing what he does next.” (39:27, Jeremy Schwartz)

• Marvin’s Rejection of Stolen Fortune

  • “Right in front of Jerry, Marvin walks over to a toilet, opens the lid and drops the piece in. Then flush. The two of them literally watch a million dollars go down the drain. Then Marvin turns to Jerry and tells him to cut it out. He's gotten away with it for now, but it's gonna blow up in his face sooner or later.” (45:39, Jeremy Schwartz)

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Timeline & Timestamps for Important Segments

• 03:01 — The ketchup kitchen: Gloria is offered a piece of the rigged game.
• 06:25–08:30 — Monopoly’s origins and parallels to real-life injustice.
• 10:35–14:00 — McDonald’s transforms with Happy Meals and gamification.
• 15:20–19:10 — The McDonald’s Monopoly phenomenon becomes a cultural staple.
• 22:26–28:00 — Jerry Jacobson’s personal and professional background.
• 28:00–31:55 — Security paranoia and path to head of security.
• 31:55–37:10 — The breakdown in security and Jerry’s opportunity.
• 37:10–43:20 — The mechanics of the heist: overhead locks, bathroom swaps, and distribution to distant contacts.
• 44:45–46:00 — Marvin's warning: a million-dollar ticket flushed, a last moral stand.

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Tone and Style

The narrative blends conversational, engaging storytelling with true crime intrigue. Schwartz blends dramatic reenactment with a touch of dark humor, keeping the listener invested in both the outlandishness of the scam and the human failings that make it possible.

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Summary

This episode lays the foundation of the McDonald’s Monopoly heist, presenting it as a cautionary tale—about the unpredictability of fate, allure of easy money, and the ingenuity (and fallibility) of those entrusted with power. It’s a story of how security, luck, and ambition interweave, and how one man’s personal insecurities and professional resentment fueled a multi-million dollar fraud.

Key takeaways:

• Even the most secure systems are vulnerable to human error and greed.
• Unfairness embedded in games—and life—often repeats itself, regardless of scale or intent.
• The story is just beginning: the next episode promises to chronicle how Jerry's scheme expands—and how it all starts to unravel.

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For more: The remainder of the series and additional resources can be found on American Criminal, including suggestions to check out the HBO series McMillions and the book by James Lee Hernandez and Brian Lazardi.

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Transcript

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[Jeremy Schwartz (American Criminal Host)]

Pushkin.

[American Criminal Podcast Narrator]

In 1987, McDonald's teamed up with the game of Monopoly to launch a hugely successful marketing campaign. Buy a Big Mac or a large fries and you could win a prize ranging from a free ice cream all the way to a million dollars. There was just one problem. The game was rigged. This story comes to you from the True Crime and History podcast American Criminal, where host Jeremy Schwartz explores the dark side of the American dream. Enjoy.

[Jeremy Schwartz (American Criminal Host)]

It's 1997 in Charleston, South Carolina. Gloria Brown's in the kitchen cooking dinner with her friend Robin Colombo. Gloria is enjoying spending time with Robin. The two have known each other for a few years, but Robin moved away from Florida a little while back and Gloria's missed the company. So when Robyn called to invite her to visit for the weekend, Gloria was all for it. It's been a strange trip, though. Gloria was hoping to catch up with Robyn one on one. She's been going through a hard time lately, and it would be nice to be able to vent a little to her friend. But Robyn's husband Jerry is just always around, which is making it hard for Gloria to really open up. She doesn't know this guy, and while he's got a certain charm to him, it feels like an act to Gloria. Like maybe he's hiding his real personality beneath the surface. So as she and Robin finish preparing the meal and bring the dishes to the table, Gloria can't help feeling relieved. She's going home tomorrow. Sure, all of her financial troubles will be waiting for her, but at least she'll be free of Jerry. The trio raise their glasses and a quick toast. And then, before Gloria's finished her first bite of food, Robyn fixes her with an intense look and says she needs to talk to her about something. Neither she or Jerry have touched their plates yet, so Gloria senses this is important. Like maybe it's the whole reason she was invited here in the first place. Trying to sound casual, she says she's all ears. That's when Robin starts talking about McDonald's. Specifically their famous Monopoly promotional game. The one that's been running for as long as Gloria can remember. She nods along, talking about the prizes she'd love to win. Mostly just to fill in the quiet while Robin lights a cigarette. After taking a drag, Robin explains that the whole thing's fixed. Those people you see on the TV saying they've won a million dollars, they didn't win anything. They were chosen. And you want to know who chooses the winners? With a dramatic flourish, Robin points to her husband. Him. He's the one with all the power. Gloria's eyes widen as she listens to her friend explaining the scheme. How Jerry's been choosing all of the million dollar winners for years now. McDonald's does it this way to make sure that only good people win the money. They don't want anyone with an embarrassing criminal history or something like that tied to the company. Gloria nods. That kind of makes sense. Then Robbins says that they want Gloria to be the next big winner. If she wants, that is. Gloria's feeling lightheaded. She's not even sure if she believes what Robbins just told her, but she really wants to. A million dollars. She can't even picture that much money. She's a single mom, and making ends meet with just one income is tough. Now her friend's just offering her money. She gazes across the table, trying to find the words to answer Robin, smiling at her, eyes gleaming with excitement. But Jerry's smile looks more like a smirk. Makes Gloria think there's more to this than Robyn's letting on. And suddenly she's wondering, should she take the money or run for her. From airship I'm jeremy schwartz, and this is american criminal. In 1903, amateur inventor and political activist Lizzie McGee put the finishing touches on a board game she'd come up with as a way to demonstrate the inequalities in America's economic system. The game invited players to move their tokens around a square board and forced them to pay rent every time they landed on a property they didn't own. She called it the Landlord's Game, and it developed a small but passionate following. Three decades later, heater salesman Charles Darrow played Lizzie's game at a dinner party with friends and saw it as a potential moneymaker. He took the Landlord's Game, removed some of the criticisms of capitalism, and renamed it Monopoly. When his stolen version of the game became a hit, Charles sold the rights to Parker Brothers, who paid Lizzie $500 so she wouldn't try to defend her patent. The company also gave her a promise in writing to credit her as the game's inventor in all future editions. It was a promise Parker Brothers never fulfill, denying Lizzie recognition for inventing a game that was becoming a staple in homes around the country. And while Lizzie McGee's role in the creation of Monopoly was quietly smudged out, Charles Darrow went on to become an incredibly wealthy man who was lauded as an early innovator in the world of board games. The point I'm trying to make is that life isn't always fair. Lizzie did everything right. She created something new and innovative. She got a patent to protect her intellectual property. Then when someone violated her patent, she negotiated in good faith and she still got screwed. Unfortunately, that's not the only time that the game of Monopoly was used to screw people out of millions. This is episode one in our three part series on the great McDonald's monopoly heist. A Man on the Inside. It's Just about lunchtime on May 15, 1940, in San Bernardino, California, brothers Richard and Maurice McDonald stand in front of their brand new restaurant, a small octagonal hut called McDonald's Barbecue. The air is full of the smell of slow cooking meats, and the brothers employees are at their stations ready to go. This McDonald's joint isn't like most other restaurants. Aside from a few stools at the counter, there's nowhere for customers to sit and eat. Instead, people are expected to drive up and place their orders with car hops, young women in short skirts and majorette boots, and then eat right there in their cars. Strictly speaking, this is not a brand new idea, but it's not the norm here in San Bernardino. So Richard and Maurice are nervous about how locals will react. Still, they're hopeful it'll be a hit. They're determined to make their fortune in the restaurant game. Maybe they'll make tens of thousands of dollars, they think. Even more if they're lucky. Course, these guys got no idea just how big their little barbecue joint will get one day. Forget thousands. The McDonald's name will one day be worth billions. And in about 50 years from now, the actions of one man will threaten to bring all of it crashing to the ground. Eight years after Richard and Maurice McDonald first opened their drive up restaurant, they shut it down. Not for good, though. By 1948, they were making $300,000 in sales each year, which would be around $4 million with inflation. That's not bad, right? Well, the brothers think they can do better. They've noticed that some of their items have been a lot more popular than others. So they want to streamline things. Less overhead, more customers, more money. When they reopen in December 1948, they go all in on their real money makers, hamburgers. They also replace their car hops with a cashier who takes orders at a counter. Plates, silverware and dishwashing staff give way to paper wrappers and cups. And they replace their old kitchen with a new, hyper efficient layout, with staff working on an assembly line to churn out burgers as fast as possible. That way, customers can get their food just seconds after they walk up, then be on their way. It's a bold gamble to take a risk on a concept that discourages customers from lingering at the restaurant. But it's one that takes off. And before long, the McDonald brothers have turned their restaurant into a franchise, with a second location in California and a third in Arizona. Gradually, they expand their menu to offer french fries and milkshakes. That's what brings Ray Kroc out to California in 1954. He's a milkshake machine salesman, and he wants to know why One restaurant owns eight of his products. When Ray pulls up to the McDonald's in San Bernardino, he sees people lining up to order trays full of burgers, fries, and plenty of milkshakes. The number of customers impresses Ray, sure, but more than that, he can't get over the pure efficiency of the place. How quickly they can churn out food for people like the McDonald brothers. Ray's keen to make a fortune for himself, and he's pretty sure he's just found his golden goose. He sets up a meeting with Richard and Maurice and convinces them to let him have the franchise rights. From there, he institutes a model of hyper efficiency in every new store the company opens. Not only will customers be able to buy their food and leave with it just moments later, they're guaranteed to have the same experience in whichever restaurant they visit. It's comfort when you're away from home. It's an easy meal when you're short on time. It's a shining example of American capitalism. By 1960, McDonald's restaurants around the country are grossing $56 million annually. And that's only the beginning. The company soon expands beyond the US with stores opening in Europe, Asia, and as far away as New Zealand. But towards the end of the 1970s, McDonald's is looking for ways to make their customers happier. In particular, they want the whole experience to become family friendly. It's a big shift from 30 years ago, when Richard and Maurice wanted to get people in and out as fast as possible. That kind of efficiency really lends itself to people looking for a quick bite on their own. But there's money to be made by enticing families to visit the restaurants, too. In October 1977, the company rolls out a marketing scheme to do just that. They're called Happy Meals, and you probably don't need me to tell you what they look like, right? Food, drink, small toy, bright box. It's not the first time toys are used to directly market to kids, but it sure is a masterclass in doing it right. Obviously, the Happy Meals are a hit. Kids love the toys, and with multiple options available, they have to come back several times if they want to collect the whole set. And for the next decade, it's one of the best marketing tools McDonald's has in its arsenal. But pretty soon, they'll launch a campaign that'll make Happy Meals look like, I don't know, child's play.

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[Jeremy Schwartz (American Criminal Host)]

In 1987, McDonald's joins forces with another American icon for their First Monopoly campaign. McDonald's promises its customers that they can win prizes that range from free burgers and sodas to new houses, dream vacations, and even a million dollars. All you have to do is collect game pieces inspired by the classic board game. Complete a set of properties and you win a prize. There are also instant win pieces that mostly give out low value items like fries and desserts. But there are some instant wins for the million bucks, just not a lot. The odds of pulling a million dollar winner are somewhere in the region of 1 and 250 million. Still, people don't let the odds stop them. They flock to McDonald's in droves, buying the products that come with game pieces, hoping to hit the jackpot. The game is a massive success, and before it's even over, executives are already talking about bringing it back the following year. Now, what's really important to know about the whole thing is that McDonald's doesn't actually have anything to do with running this Monopoly promotion. The people behind the scheme are a company called Simon Marketing, the same team who helped develop the Happy Meal. McDonald's knows Simon can deliver. So they're responsible for everything from start to finish. McDonald's contracts them to print the game tokens, send them to stores, and carefully disseminate the high value pieces across the country. That means that McDonald's corporate has no idea where the winners will be when the pieces turn up. Well, except at McDonald's restaurants. They'll definitely be there. In 1988, the campaign returns and McDonald's sees a huge jump in sales during the months that it runs. Sure, they have to pay out millions in prizes, but the increased profits more than cover the expense. If customers want more tokens, they can buy more products. It's almost like gambling, but for legal reasons, it's not technically gambling. The game creates a feeling of excitement around the McDonald's brand. Almost 50 years after the first barbecue stand opened in San Bernardino, it's more crucial than ever that the company continue finding new ways to reinvent itself to stay on the cutting edge of the fast food industry. This does that for them every year, sometimes multiple times a year. It's not always Monopoly themed, but the basic concept stays the same. Buy products, get game pieces, collect the set to win. And with every new version of the promotion, they run ads featuring people who won prizes the last time. Cars, vacations, jet skis, cold hard cash. Everyday people are really winning these things. All they had to do was go directly to McDonald's. On the surface, it seems like there's no downside to this. People can go get a burger, some fries, maybe have a fun meal out with their family, maybe win a camcorder or new tv. And in the back of their mind there's that exciting thought that they might just be one of the lucky ones to find that million game piece. For the first couple of years, the game runs exactly as planned. Everyone's got the same 1 and 250 million chance of becoming an instant millionaire. But in 1989, one man will find a way to corrupt this incredibly popular game. He'll take it upon himself to see that no one in America will genuinely win those million dollar prizes ever again.

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[American Criminal Podcast Narrator]

Foreign.

[Jeremy Schwartz (American Criminal Host)]

It'S the spring of 1980 in Hollywood, Florida. Jerome Jacobson lies in a hospital bed, frustrated and kind of scared. A few days ago, 37 year old Jerry collapsed with a terrifying paralysis that affected his legs, arms, eyes and respiratory system. His wife Marsha rushed him to the emergency room and he's been stuck in a bed ever since, waiting for answers. Since he's arrived, he's slowly regaining the feeling in his limbs and his vision is coming back, but he's ready for this nightmare to be over. Beside him, Marsha asks Jerry if he wants another sip of water. He shakes his head. He doesn't want a drink, he just wants answers. Just then, as if responding to his prayers, a doctor walks into the room and announces that they finally got results back on their tests. Jerry shuffles in the bed, trying to sit up a little straighter, but he can't even manage that. Resigned to his discomfort, he tells the doctor he's ready to hear the worst. Slowly, she explains that he has Guillain Barre syndrome, which means his body's immune system is attacking his nerves. It's a Rare condition, and there's no known cure. But it's possible to make a recovery with careful treatment and rehabilitation. Still, it'll be a tough road ahead, and Jerry's life will probably look different from now on. He might live with muscle weakness for a number of years, and he'll need plenty of support from his loved ones. Jerry's mind is reeling as he takes all of this in. He hates feeling like he's dependent on other people, like he's a burden. All his life he's just wanted to feel like he's in control, that he has true agency over himself. Now it sounds like he might never have that again. Jerry Jacobson was born in Youngstown, Ohio, in 1943. And he had a pretty unremarkable childhood. He grew up with a stepbrother, Marvin, who always seemed to get more than Jerry. More favors, more affection, more opportunities. But he tried not to let that get to him. One day, he'd leave all that behind. He had big dreams of getting a job that gave him plenty of authority and respect. And in his early 20s, he enlisted with the Marines. Unfortunately for Jerry, his time in the armed forces was short lived. His heart was in it, but his body wasn't. He was discharged during basic training thanks to his high arches and persistent allergies he'd had all his life. It was devastating for him to be told that he would never do a job he'd been dreaming about for years. But he didn't dwell in his misery for long. In 1976, he pivoted, enlisting as a police officer in Hollywood, Florida. It might not have felt quite as prestigious as the Marines, but it was a job that came with built in authority and a less physically rigorous screening process. And for a little while, things seemed to be going well for Jerry. Then, about a year after he was sworn onto the force, he injured his wrist on the job. It was so bad that he had to take extended medical leave while he was still off work. In 1980, he started experiencing extreme pain in one of his hands, which soon developed into a creeping numbness and eventually the paralysis that landed him in the hospital. The diagnosis of Guillain Barre syndrome is just one more blow that Jerry really doesn't need. He was already feeling pretty useless not being able to work. And now his wife will also have to take time away from her job on the force to care for him. After he's discharged from the hospital, Jerry goes home, where Marsha has to bathe and feed him every day and give him massages to help his Recovery. But although she obviously loves her husband deeply, she doesn't let him wallow. She says he can have 15 minutes to feel sorry for himself each morning. But then he has to get on with it. His life misery's no good here. With Marsha's support, Jerry shows clear signs of improvement. But it's obvious that he'll never be able to rejoin the police force. In 1981, the Hollywood PD let him go, meaning that he's got to start over once again. After that, Jerry and Marsha decide that Florida's brought them enough bad luck for one lifetime. So they move north to Atlanta, Georgia. By now, Jerry's recovered enough that he picks up some work as a mechanic. But Marsha's still the breadwinner. She leaves her police job behind to take a position as a security auditor for an accounting firm. Now, her new employers could assign Marsha to any of their clients, but they just so happen to place her with the Dittler Brothers. A printing company. This sounds kind of dull, right? A printing company. Well, what if I told you that Dittler had built its reputation by printing things like scratch offs, lottery tickets and promotional games for other companies? Huh. That suddenly seems more interesting. It's certainly a job that Marsha enjoys. And it's something she thinks Jerry is well suited to as well. So she recommends him for a role at the company. And soon, husband and wife are working side by side. Unfortunately, the Jacobsons are not a couple who should be working so closely together. They get into a lot of little arguments on the job, which spill over into blow ups at home. By 1983, they're divorced but still working together. And like his ex, Jerry takes his job with Dettler Brothers very seriously. He likes the respect it gives him, the feeling of control he has keeping a handle on the firm's production of high value pieces of paper. In 1987, Dittler are contracted by Simon Marketing to create and distribute all of the game pieces for the new McDonald's marketing campaign. this stage, Jerry's been with the company for around six years and is pretty high in their security team. So he's given the job of overseeing everything related to the Monopoly promotions. It's a gig he loves Being responsible for. The integrity of this high profile partnership is exhilarating, and he's determined to impress among the Dittler employees. Jerry gets a reputation for being a real pain in the ass with this Monopoly thing. He starts checking people's shoes to make sure no one's smuggling game pieces out of the factory. He also institutes a rule that employees who transport the pieces aren't even allowed to use the bathroom alone. There will be no corrupting this game. Not on his watch. Of course, making sure that hundreds of millions of game pieces remain under Dittler's control is only part of the job. The most important aspect, though, is taking care of the winning tokens, the rare property titles the customers will need to complete the set, and the big ticket instant wins. Those get an extra level of attention. For starters, they're each printed using blacklighting and feature tiny flaws in the text, a corner missing from the crossbar of a letter T or a slightly crooked punctuation mark. That way, they'll be almost impossible to counterfeit. Once these winning pieces come off the printer, Jerry locks them away in a vault with multiple layers of security until the time comes for the prize draw. Now, here's where things get more complicated. Before the start of each Monopoly campaign, a computer program is used to determine where the high value pieces will be sent. In other words, the winning tokens aren't just inserted at random into packets of other game pieces and then sent out into the world. What happens is this program will randomly select the location of another printing shop that makes McDonald's packaging, and that's where the pieces will be set. So in theory, Simon Marketing and Dittler Brothers will know what areas winners will come from ahead of time because they're the ones bringing the pieces there. And because these game pieces are so valuable, Jerry doesn't trust just anyone to bring them to their final destination. No, no, it's a job. He only trusts one person with himself. So when it's time to send the pieces out into the wild, Jerry and an independent auditor insert a winner into an envelope with a bunch of regular game pieces. The envelope is then sealed using a tamper proof holographic sticker. If anyone opens the envelope, the broken sticker will be a dead giveaway. And these stickers are specially created by another company just for this campaign. So it's not like someone can buy extras to stage some kind of heist. Anyway, Jerry and this auditor lock the envelope into a briefcase with a combination opening. He chooses the code for one side, she chooses the code for the other. There's no way for one of them to get into it without the other being there. Then they board a plane together. Jerry's got the briefcase handcuffed to his wrist. Then they fly to the airport closest to the chosen factory. Once they get there and Jerry and the auditor open the briefcase in front of all the employees. Then Jerry makes a big show of opening the envelope and carefully inserting the pieces into the packs that will be sent to the nearby distribution points. The dozen or so extra pieces are there to make sure that no one can track which box contains a winner. Like I said, it's a complicated process, but it's one that Jerry takes a lot of pride in. And it's a role he's well compensated for. In 1988, Simon Marketing hire him away from Dittler Brothers to be their head of security. There, he earns four, maybe five times what he'd be making as a cop, which is nice. But it's not just the money. He likes getting to travel regularly and quickly becomes obsessed with getting gold status. With his airline miles on board the plane, he has a habit of flashing his old police badge around when people ask him about the briefcase chained to his arm. It all feels like he's won at last. After a lifetime of setback after setback, Jerry's finally found where he's supposed to be. He's got money, job satisfaction, and the kind of authority he's been searching for for years. Under his watchful eye, the first couple of Monopoly campaigns go off without a hitch. Sales at McDonald's go up. Customers win millions of dollars worth of prizes, and everyone's happy. The employees at Simon Marketing and Dittler Brothers pat themselves on the back for a job well done. And at the center of it all is Jerry Jacobson. But despite his outward commitment to rules and integrity, Jerry's far from perfect. And soon enough, the temptation to cheat the system will prove too great to resist.

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[Jeremy Schwartz (American Criminal Host)]

It's the summer of 1989 and 46 year old Jerry Jacobson is just arriving at a family barbecue. He walks inside his cousin's house and heads straight to the kitchen so he can put his beers in the fridge. Then, after making the rounds to say hello to his relatives, he heads back out to find his brother. Technically, Marvin Braun is Jerry's stepbrother, which is important for the purposes of this Story Jerry finds Marvin by the grill and pulls him aside. They need to talk, he says, and he leads Marvin away from the noise to a secluded spot in the backyard. Once they're alone, Jerry thrusts a hand into his pocket and pulls out a small plastic bag. He hands it to Marvin, who inspects it. Inside is a single game piece from the latest McDonald's Monopoly promotion. But unlike most of the pieces Marvin's seen in the past, this one doesn't look like a typical property square from the board game. There's just text here revealing that the bearer has won $25,000. About a month ago, Jerry mentioned to Marvin that he might be able to get his hands on this exact game piece. Everyone knows that Jerry works for the company that manages the monopoly game for McDonald's, but it still didn't seem possible that he'd just be able to produce a winning ticket whenever he wanted. Now he's essentially handed his stepbrother a check for 25 grand. Marvin should send the game piece in, he says. Then they can Split the winnings 50. 50. Marvin Blinks, inspecting the small token in his hand, while Jerry explains exactly what he has to do to claim the prize. Jerry is very proud of himself for pulling this off, and if it works out, he's sure he'll be able to do it again. Exactly how Jerry manages to get his hands on the first few winning game pieces isn't clear, but it's possible that the instant win prizes below a certain dollar amount aren't guarded quite as fiercely as the major ones. However it happens, Jerry successfully hands off a winning piece to his stepbrother in 1989, and Marvin claims the 25 grand without a hitch. Jerry probably chose Marvin as his test case, not because they're especially close, but because they don't share a surname. That means Marvin wouldn't set off any alarm bells when he claimed the money. But Jerry knows he needs to be more careful the next time he pulls the stunt. The last thing he wants is a trail of friends and relatives who want a bunch of money from McDonald's. Now, the monopoly campaign's been around for a few years at this point, and it's so popular that anyone who knows Jerry knows that he's a charge of the prizes. It's like he's their man on the inside. For the people bold enough to ask him for a favor, his local butcher in Atlanta is one of the first to come to Jerry and make the request. He wants to win a prize, but Jerry's not sure that's a Good idea. It'd be too easy to make the connection between the two of them, he says. But the butcher isn't fazed. He'll find a distant relative to claim the prize. After thinking it over for a few days, Jerry decides, yeah, it's a good plan. Of course, he's not just going to give the winning piece away. With Marvin, he asked for a 50% cut of the money, but he's willing to take less this time. So he sells the $10,000 instant winner to his butcher for $2,000 cash. Easy money, but I mean, it's. That can't last. Eventually, the fervor around the Monopoly game gets so big that McDonald's decides it's time to change up its procedures. Instead of individual game pieces that get handed to customers with their purchase, the tokens are peeled off, a secure role behind the counter. So for the next couple of years, Jerry is cut out of the chain of distribution and his little side hustle is put on hold. But it's only temporary. It's 1995, and Jerry Jacobson's 52. Just before 9am he pulls into his parking spot at Simon Marketing and heads inside. It's one of the days he needs to use his cane. Since his Guillain Barre diagnosis 15 years ago, the cane is something he has to rely on from time to time. Now he makes his way through the building and up to his office. That's when he sees it. A box on his desk. It's smaller than a shoebox and has stickers marking it urgent and fragile. Curious, he sits down and grabs a pair of scissors to cut through the tape. Inside is just one thing, but it's worth millions. It's a thick roll of holographic stickers, the kind Simon Marketing and Dittler Brothers used to transport the McDonald's Monopoly game pieces. Recently, the campaign has evolved. Now the tokens are stuck directly onto product packaging, like cups and fry boxes. So Jerry's once again responsible for bringing the winning pieces around the country, where they're applied at random during the production process. Just to be clear, these stickers absolutely should not be on Jerry's desk. They should have been delivered to someone else at the company, because giving him access to a huge supply of these stickers is removing a key obstacle to getting his hands on the big ticket prizes. Jerry recognizes that right away, and his brain kicks into high gear. It's time to restart his scheme. And this time, he's gonna take it up a notch. By the time the stickers are mistakenly delivered to Jerry Jacobson's desk. He's become disillusioned with the job he used to think made him special. It's nothing his company's done. It's their client, McDonald's. Later, Jerry will tell the story like he's in the room when the computer program is randomizing where winning game pieces will be sent to. That's standard, but that day the system designates a factory in Canada as the lucky destination. Before anyone could start the process to bring the pieces up north, though, McDonald's executives order Jerry to run the program again. They don't want any of the big winners going to Canada ever again. This is Jerry's version of events, and there's no public evidence backing up his story. But he'll later point to this moment as his reason for doing what he does next. Because after he gets his hands on those stickers, Jerry uses them to steal the highest value game pieces. And how he does it is laughably simple. Remember that the envelopes containing the winners are locked in a briefcase. Jerry puts the code in for one lock, and the independent auditor chooses the other code. They're each supposed to look away while the other sets their code. But Jerry just makes a show of looking away. He quickly peeks while the auditor spins the dials. Now he's got both codes to open a brief case. Still, once the envelope is inside the case, it's handcuffed to Jerry's wrist and the two of them go straight to the airport. The auditor's by his side the entire time. That's her job to keep him honest. But Jerry finds an easy workaround. Once they get off the plane at their destination, he says he's got to use the bathroom. Then he just walks into the men's room alone. While the auditor waits patiently outside, Jerry locks himself in a storm stall, opens the briefcase and removes the envelope. He peels the sticker up, tips the couple dozen pieces into his pocket, and replaces them with a bunch of worthless pieces he swiped from the factory. Then he reseals the envelope with a brand new sticker, locks it inside the briefcase again, and heads back to meet the auditor so they can carry on with their task. No one ever notices what he's doing. Doing. So Jerry easily starts making off with every high value ticket he can get his hands on. The only problem now is what to do with them. Obviously, he can't claim them for himself, but he's got to be careful about who he gives them to. He can't have anyone ratting him out. After the successful test case with his stepbrother Marvin. Jerry figures that he's someone he can trust. But Marvin's not interested. He owns a successful business and he doesn't need the money. So when Jerry starts giving him more winning game pieces, Marvin tells his stepbrother that he doesn't want them. Hell, he even drops a couple into Salvation army donation tins. And one night when Jerry hands him the big one, I mean the big one, a million dollar instant win piece, Marvin knows exactly what to do to get the message to through to his brother. Right in front of Jerry, Marvin walks over to a toilet, opens the lid and drops the piece in. Then blush. The two of them literally watch a million dollars go down the drain. Then Marvin turns to Jerry and tells him to cut it out. He's gotten away with it for now, but it's gonna blow up in his face sooner or later. Jerry sighs and tells Marvin he's right. He'll stop stealing pieces. It's not worth the risk. Marvin goes home that night thinking he's turned his brother around. But here's the deal. Jerry Jacobson is a liar. He's not going to stop. In fact, he's just getting started. From Airship this is episode one in our series on the great McDonald's monopoly heist. On the next episode, Jerry starts finding allies to help him recruit winners for his scheme. But with every person who gets roped in, the risk of getting caught goes way up. We use many different sources while preparing this episode. A few we can recommend are the Daily Beast article How an ex Cop Rigged McDonald's Monopoly game and Stole Millions by Jeff Mason, the HBO documentary series McMillions, and the book of the same name by James Lee Hernandez and Bryan Lazardi. This episode may contain reenactments or dramatized details, and while in some cases we can't know exactly what happened, all our dramatizations are based on historical research. American Criminal is a co production of Airship and Evergreen Podcasts. It's hosted, edited and produced by me, Jeremy Schwartz Arts Audio editing and sound design by Sean Rule Hoffman Music by Thrum this episode is written and researched by Joel Callan, Managing Producer Emily Burke. Executive producers are Joel Callan, William Simpson, and Lindsey Graham.

[American Criminal Podcast Narrator]

If you want to know how Jerry's story ends, you can find the rest of the great McDonald's monopoly heist and many more true stories of crime and punishment over on American Criminal wherever you get your podcasts.

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[Jeremy Schwartz (American Criminal Host)]

So good. Your bill, ladies. I got it.

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