Armchair Expert with Dax Shepard - You Might Enjoy: The Big Flop

Episode Date: May 22, 2025

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.

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? 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. 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 podcast. Remember when a big, beautiful, family-sized house cost $250,000? Something like that today would be, what, triple the price? 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. It's the Monopoly game, only at McDonald's. With over 50 million prizes, prizes and 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. On a sinking ship From Wondery and Atwill 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 super-sized 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. We are also joined by another comedian and podcast host

of Sweet Hearts Podcast and we called your mom, it's Beth Stelling. Hi, thanks 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?

It felt like they kept moving the finish line. I mean, I'm over here getting repeat after repeat, such a disappointment to peel that off the wet cup and or the fries and find out you just have another frickin Park place. Oh, yeah. Oh, yeah, I was all in I would probably just really made McDonald's sales numbers jump whenever it came around because 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. I feel like people were like truly just getting the fries and ripping it off and then throwing the fries in the trash. I'm like, not another one. 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 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 hamburgers. You know what I mean? Now, the way the Monopoly game works is when you buy something in 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. 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. Collect these for a $250,000 home. What? A home? I don't remember that.

Yeah, I didn't know that. You were winning houses? That's... That was in 87, so... Yeah, that's true. Houses were way cheaper. Way cheaper. And that looks like the McAllister home from Home Alone for $250,000. Today, that's what? $2 million. We will drop this house on top of your house.