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Armchair Expert with Dax Shepard

You Might Enjoy: The Big Flop

Thu, 22 May 2025

Description

On each episode of Wondery’s podcast The Big Flop, comedians join host Misha Brown to chronicle one of the biggest pop-culture fails of all time and try to answer the age-old question: who thought THIS was a good idea?The Hamburglar was just a mascot, but Jerome Jacobson was the real deal — a McDonald's security chief who pulled off the ultimate inside job. While millions of Americans peeled game pieces hoping for a miracle, this master manipulator was turning Big Macs into big bucks, orchestrating a multi-million dollar fraud. Discover the supersized story of how one man's greed turned America's favorite promotion into the biggest McFlop in fast-food history.This is just a preview of The Big Flop. Listen to The Big Flop wherever you get your podcasts, or at wondery.fm/thebigflop_armchair.See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info.

Audio
Transcription

Chapter 1: Who is Jerome Jacobson and what did he do?

0.389 - 24.873 Misha Brown

The Hamburglar was just a mascot, but Jerome Jacobson was the real deal. A McDonald's security chief who almost pulled off the ultimate inside job. Hi, I'm Misha Brown, the host of Wondery's podcast, The Big Flop. Each week, comedians join me to chronicle pop culture's biggest failures and try to answer the age-old question, Who thought this was a good idea?

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Chapter 2: What was the genius idea behind McDonald’s Monopoly?

25.513 - 44.714 Misha Brown

At the time, the McDonald's collab with Monopoly was a genius idea. Come get a Big Mac and you could go home with a million dollar prize piece. The only problem? When they picked their head of security, the one guy in charge of protecting those million dollar pieces, Let's just say McDonald's drew the wrong card.

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Chapter 3: What went wrong with the McDonald’s Monopoly game?

45.074 - 71.973 Misha Brown

Comedians Ify Wadiwe and Beth Stelling join me to break down what really went down with the McDonald's monopoly scandal. You're about to hear a preview of The Big Flop. Watch full episodes of The Big Flop on YouTube or listen wherever you get your podcasts. Remember when a big, beautiful, family-sized house cost $250,000? Something like that today would be, what, triple the price?

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72.553 - 97.952 Misha Brown

Well, imagine you get that house for free. Grandpa gets a million dollars and your best friend wins a brand new car, all thanks to the McDonald's Monopoly game. If that sounds too good to be true, that's because it is. Unless, of course, you're the Robin Hood of scammers, or I guess, in this case, the Hamburglar of scammers. Let's get into it, besties.

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Chapter 4: How did the Monopoly scam work for over a decade?

99.293 - 115.364 Ify Wadiwe

It's the Monopoly game, only at McDonald's. With over 50 million prizes, it's supersized excitement. For years and years, the game was compromised. It was rigged. The scam worked for more than a decade, with the crooks making off with more than $24 million.

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Chapter 5: What are the thoughts of comedians on the Monopoly game?

126.744 - 154.861 Misha Brown

From Wondery and at Will Media, this is The Big Flop, where we chronicle the greatest fails, blunders, and flubs of all time. I'm your host, Misha Brown, social media superstar and supersized drama queen at your bestie, Misha. And on our show today, I'm so excited, we have an actor, a comedian, and writer. It's Ify Wadiwe. Hey. Hello. Hey, how's it going? So, so good. Woo-woo. Woo-woo.

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155.765 - 179.029 Misha Brown

We are also joined by another comedian and podcast host of Sweethearts Podcast. And we called your mom. It's Beth Stelling. Hi. Thank you for having me. So excited. So before we get into the whole story of McDonald's and the Monopoly game, what do you remember yourself about the McDonald's Monopoly game?

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Chapter 6: Why did players feel disappointed with the game?

179.329 - 193.115 Beth Stelling

It felt like they kept moving the finish line. I mean, I'm over here getting repeat after repeat. It's such a disappointment to peel that off the wet cup or the fries and find out you just have another freaking park place.

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193.896 - 215.289 Ify Wadiwe

Oh, yeah. Oh, yeah. I was all in. I probably just really made McDonald's sales numbers jump whenever it came around because the way they did it is you'd always get two. You'd always get two, so you were always hunting down one. And giving you that two made you think you were closer than you always were, even though everyone had the same two. It's so true.

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225.459 - 225.579 Ify Wadiwe

Okay.

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226.099 - 246.017 Misha Brown

Well, today we are talking about how one man managed to cost McDonald's a whole lot more than Monopoly money by taking one of its most popular promotions of all time. And yes, this story does end with someone going directly to jail. So the board game Monopoly was invented in the beginning of the 20th century.

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246.197 - 272.154 Misha Brown

And by the 1980s, it's become an American institution, just like another M name we all know and love, McDonald's. I'm loving it. So the idea to combine these two iconic brands comes from a company called Simon Marketing in 1987. And Simon Marketing also came up with Happy Meals. So, I mean, they know a thing or two about selling food. Hamburgers. You know what I mean?

273.815 - 292.485 Misha Brown

Now, the way the Monopoly game works is when you buy something at McDonald's, there are Monopoly game pieces attached to your drink or your fries package or your burger box. You can also find the pieces in ads in magazines and newspapers, which I did not remember that. The pieces are covered by little flaps that you peel off.

292.805 - 307.351 Misha Brown

And if you find the right combination of Monopoly pieces or the instant win pieces, you win a prize. So let's take a look at an ad for the Monopoly game from 1987. You win a dream vacation.

307.451 - 316.806 Beth Stelling

Collect these for a $250,000 home. A home? I don't remember that.

316.846 - 318.968 Ify Wadiwe

Yeah, I didn't know that. You were winning houses?

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