Crazy Secrets About Monopoly

Knowledge

June 5, 2025

19 min read

Let's delve into some crazy Monopoly secrets!

CRAZY Secrets About Monopoly! by BE AMAZED

Monopoly is one of the most popular board games in history. Since it first hit the market in 1935, over 250 million sets have been sold, and the game has been played by more than one billion people worldwide. But how much do you really know about this global favorite? From its controversial history to rules you’ve never even heard of and a scandal that rocked the world, get your game faces on for this special Monopoly edition of the ultimate fact show.

Who Invented Monopoly?

One evening in late 1932, a Philadelphia businessman named Charles Todd and his wife Olive introduced their friends Charles and Esther Darrow to a real-estate boardgame they’d recently learned. The game had no name, and it was passed from friend-to-friend rather than sold in a box. But the rules were already familiar: roll the dice, enthusiastically move your tokens around the board and buy up property as you go.

Charles Todd introduced monopoly to his friend

Charles Darrow, who was unemployed at the time, enjoyed the game so much that one day he asked Todd for a copy of the rules. Todd had never written them up before and didn’t believe that a written version of the rules had ever existed either.

But he was wrong. In fact, the game had been invented in Washington DC way back in 1903 by a daring and progressive woman named Elizabeth ‘Lizzie’ Magie. But Lizzie’s legacy would be cruelly erased for decades to come as Monopoly’s glory was handed over to the man who had picked it up at his friend’s house.

Charles Darrow went on to sell the rights to Monopoly to the Parker Brothers in 1935, who helped him develop it into the roaring success it is today. Darrow made his millions off the game and has been remembered throughout history as Monopoly’s inventor. But that couldn’t be further from the truth.

When Elizabeth Magie sat down to think up the game in the early 1900s, she was an unknown woman working as a stenographer. Boardgames were becoming increasingly commonplace in middle-class homes, and Lizzie wanted to create one that taught people about real estate, income inequality and the successes and failures of life.

Her original design included all the elements of the modern board, and she named her creation: The Landlord’s Game. She created two versions: an anti-monopolist set in which all were rewarded when wealth was created, and a monopolist version where the goal was to create monopolies and crush your opponents. Unbeknownst to her, it was the Monopoly rules that would later catch on.

Lizzie entered the U.S. patent office on 23rd March 1903 to secure her legal claim to the Landlord’s Game and published it at least two years later. Its popularity spready throughout the next three decades and eventually caught on with a community of quakers in Atlantic city, which is probably how it made its way to Darrow.

When Monopoly took off in the mid-1930s, Parker Brothers bought up the rights to other related games to preserve its territory, which included The Landlord’s Game. For the patent and two other game ideas, Lizzie reportedly received $500 and no royalties. Though she protested angrily that the new Monopoly game made no mention of her story, Lizzie faded into obscurity and died a widow with no children in 1948.

Although attempts have been made to re-write Lizzie into the games history Hasbro still downplays her role, and their official history of the game even “begins” in 1934. One of Lizzies last jobs was at the US Office of Education, where her colleagues remembered her as an elderly typist who talked about inventing games.

Monopoly helped allied prisoners of war escape during WW2

Monopoly may be the cause of some serious tensions, but this quaint little game actually saved lives during World War Two! During the war, large numbers of British airmen were felled over enemy airspace and then held as prisoners behind enemy lines. But thanks to the Geneva Convention, Germany allowed humanitarian groups like the Red Cross to distribute care packages to those prisoners.

One of the categories for theses care packages was games and past times. You understand where this is going, right? The Allies took military advantage of this surprising act of empathy by posing as charities who would send care packages to their prisoners of war. And by care packages, we mean clandestine escape kits containing tools like compasses, metal files, money and, most importantly, maps.

To eliminate their chances of discovery, these kits were disguised as Monopoly sets. The compasses and files were disguised as playing pieces, real bank notes were squirrelled away below the Monopoly money, and the maps were concealed within the boards themselves.

Monopoly boards hiding maps and money

The kit was developed by MI9, the British Secret Service unit responsible for escape and evasion, who collaborated with John Waddington Ltd, the U.K. manufacturer of Monopoly at the time. Captured soldiers were told that the “special edition” monopoly sets would have a red dot on the Free Parking space, something that would look to an untrained eye like a standard-issue printing error.

Once they’d obtained the playing pieces within them, they were instructed to destroy the games. British historians now estimate that the secret Monopoly boards could have helped thousands of captured soldiers escape. Did someone say get out of jail free card?

What’s the story behind the Monopoly pieces?

Some of the most recognizable aspects of Monopoly are its eclectic mix of playing pieces. Plenty have come and gone over the years, with old favorites getting the boot in favor of some questionable new ones. When Monopoly was first introduced to the world in 1935, there were just six playing pieces: the top hat, the thimble, the iron, the boot, the battleship and the cannon.

But what’s the story behind these odd tokens? Originally, Charles Darrow, the guy who stole the idea from poor Elizabeth Magie, envisioned players using small items from around their homes as playing pieces. But it wasn’t until his niece suggested that the pieces could be charms from a girl’s charm bracelet that the iconic pieces were born!

As new versions of the game were released, so too were new pieces. In 1935-1936, the race car, the purse, the rocking horse and the lantern were added, with the race car being the only surviving piece today. In the 1950s and beyond, the Scottie dog and the wheelbarrow were added to the roster alongside a few more scrapped pieces.

And in 2017, Hasbro shook things up again when it allowed players to vote out three of the original pieces in favor of 50 new designs. Eventually, it was the trusty thimble, the boot and the wheelbarrow that got the chop, while the rubber ducky, penguin and T-Rex were added; at least it wasn’t that awful hashtag!

Monnopoly pieces

There’s no word on whether Darrow cut his niece a juicy check for thinking up one of the most iconic parts of the game, but considering the actual game itself wasn’t his idea either, you'd doubt she got a penny.

Who is Mr. Monopoly?

Besides the dude on the Pringles can, Mr. Monopoly is one of the most iconic mustachioed characters in popular culture, but who is he?

First and foremost, his name isn’t even Mr Monopoly. When the character was first created during the depression-era 1930’s, he was named Rich Uncle Pennybags. When Parker Brothers were first approached by Darrow, they originally rejected Monopoly on the basis of “52 fundamental errors”. But Darrow was not deterred. He printed 5,000 copies of the boardgame continued to sell it independently on the street with Rich Uncle Pennybags as its mascot.

By the time Parker Brothers did get on board with the game, the character was already well-known enough to front other of the company’s board games. In 1940 he became the star of a game called Dig, and in 1946 he fronted the eponymous Rich Uncle game.

It has also been said that Mr. Monopoly was possibly inspired by J.P. Morgan, a powerful banker who helped finance the construction of railroads and organized several major corporations, including General Electric. The identity of the designer of the character, artist Dan Fox, was unknown until 2013, when a former Parker Brothers executive named Philip Orbanes was contacted by one of Fox’s grandchildren. And Mr. Monopoly isn’t the only character in the game, either. Officer Mallory is the officer in charge of the jail, and Jake the Jailbird is the dude behind bars! Who knew?

McDonald’s Monopoly once caused an epic scandal!

Back in 1897 McDonalds launched a new, unique sales promotion that would soon be hotly anticipated for decades to come: McDonald’s Monopoly. Anyone who frequents the fast-food chain when the promotion is on will know that it’s essentially a big prize draw.

There are two ways to win: first, by peeling-off little tokens that sometimes offer free menu items, or by collecting property sets, just like in the real game, which boast big prizes like cash, new tech and even all-expenses paid holidays!

Besides the fact that it encourages the consumption of some of the world’s most unhealthy foods, it all sounds like a bit of wholesome fun, right? Well, fun isn’t exactly the word many people would use to describe the scandal that went down in 2001, when one man scammed McDonald’s Monopoly out of an eye-watering $24 million dollars. For twelve years, almost nobody legitimately won prizes from the Monopoly game. Instead, nearly all winners were in some way connected to one man who was secretly stealing the most valuable prize tokens: Jerome P. Jacobson.

McDonald’s circulates a few rare tokens that read “Instant Winner!” which don’t require participants to have a full set of game pieces. These are the tokens that were guarded most carefully by the company’s security team. A security team that included one Jerome P. Jacobson.

At first, Jacobson was a model security officer, he even inspected workers shoes to make sure they weren’t stealing from the company. But things soon changed. At one point, McDonald’s reorganized the distribution of the prize tokens so that they prioritized the United States over Canada.

When Jacobson saw what they were doing, he realized how easy it would be to get his hands on the winning tokens. By this point he’d been promoted to head of security, meaning it was his job to transport the winning tokens and personally place them on the packaging factory line.

Jerome P. Jacobson McDonald's monopoly

Jacobson had received a package that was accidentally sent to him from a supplier in Hong Kong, containing a set of anti-tamper seals that would allow him to switch out the winning tokens. Because he was always accompanied by another member of security on his travels, he would sneak to the bathroom, make the switch and pocket his prizes.

He knew he couldn’t claim them himself, that would be far too suspicious, so he sold them to distant friends and took a cut of their winnings. Between 1995 and 2000 he earned his associates $24million in stolen prize money.

McDonald's monopoly Jerome P. Jacobson

Having stolen some records which proved the Canada switch up had happened, Jacobson figured that his position at the company was safe. But then he went full Robin Hood with his new-found power. One morning, the staff at the St. Jude Children’s Research Hospital in Tennessee were dumbstruck when they received an anonymous envelope containing a million-dollar instant win Monopoly token.

Despite a full investigation, nobody could figure out where the envelope came from. Jacobson thought he was in the clear, until several years of stolen prizes finally led McDonald’s bosses to get the FBI on board. Eventually, one of Jacobson’s co-conspirators snitched anonymously, and his trail of masterful fraud was discovered.

It turned out Jacobson had also roped in members of the Colombo Mafia to participate in his scheme, and, in a massive sting, the FBI indicted over 20 people who had been involved. Jacobson was sent to jail, without passing Go, on 10th September 2001.

Not all of his accomplices faced jail time. Some were simply ordered to repay their winnings, $50 a month, for the rest of their lives. But even with this agreement, McDonald’s did not expect to get all their stolen money returned to them. Would the real Hamburglar please stand up!

Jerome P. Jacobson McDonald's monopoly scam

Who is the best Monopoly player in the world?

Believe it or not, Monopoly can be considered an actual sport. And just like sports, there are championships. In total, fourteen Monopoly world championships have been held, with the most recent taking place in Macau on September 8th, 2015.

Throughout the years, additional rules for tournament gameplay have been added to account for the ambiguities in the official rulebook. There have been 14 different champions from all over the world since the first ever tournament was held in Catskills, New York in 1973, but the current reigning champion hails from Italy.

After 10 hours of property space purchases, paying rent and passing GO, Nicolò Falcone from Venice beat out 27 fellow competitive Monopoly players to come out triumphant. The grand prize was $20,580, which may seem like a random figure, but it’s actually the total equivalent of the bank in a standard Monopoly game!

Nicolò is a 34-year-old stand-up comedian who managed to knock out defending champion Bjorn Halvard Knappskog, USA Representative Brian Valentine and Japan’s Grand Champion, Tsutomu Doita, to win the title. But what’s his secret?

Nicolò’s strategy for winning the tournament was to purchase all the railroads, but he also recognizes the importance of using jail as a safe space in the latter half of the game. Until the next world championship takes place, this Italian funny man can proudly say that he’s the best Monopoly player in the world!

What’s actually supposed to happen when you land on ‘free parking’?

The rules of Monopoly have always been up for debate. No matter how much you try to play it by-the-book, there will always be someone who claims you’re playing it wrong. But one of the most hotly debated topics is this: what exactly is supposed to happen when you land on free parking?

According to the copy of the rules slipped into every copy of Monopoly ever sold, Free Parking does nothing. Despite it being a mere space for your kitschy playing piece to rest while you count your money, Hasbro has also stated that they receive hundreds of calls from bemused customers asking for clarity every year.

As a result, the company decided to conduct a study of Monopoly players, which helped them discover that a shocking 68% of respondents admitted they’d never actually read the rules, can you imagine something so ludicrous? Some people love nothing more than a good flick through a riveting rule book of an evening.

Monopoly rulebook

What’s more, they found that 30% of people just made up their own rules! This discovery inspired Hasbro to include with a new set of so-called “house-rules” with the game. One of the most popular of these rules is that every tax dollar and fine goes into the center of the board and is then given to whatever player lands on Free Parking. Talk about a bonus!

You’ve probably been playing Monopoly all wrong

The free parking rule isn’t the only one that’s sure to get your knickers in a twist. After decades of people simply ignoring the rule book, the likelihood is that there’s plenty you don’t know when it comes to how the game should be played.

In fact, according to a viral 2005 blog post by Johnny Nexus, basically everyone is playing the game wrong, which makes it much longer than it needs to be. According to Nexus, the major mistake is that whenever someone lands on a property and doesn’t choose to buy it, most people just move on to the next players turn.

What you’re actually supposed to do, according to the official rulebook, is to auction off the unowned property to the highest bidder. This not only encourages more interaction between players, rather than just hanging around until your turn, but also speeds the game up slightly.

The reason why the rule may have fallen out of the favor over the years is that it might encourage more family confrontation. After all, Monopoly is competitive enough without risking a heated auction every time someone rolls the dice!

Monopoly game family feud

And that’s not the only rule that may have slipped under your radar. Did you know that when you land in Jail, you can still buy and sell property? Yes. Landing in jail doesn’t stop you from making any money and is no real set back for a rich enough player, a bit like in real life!

How to win Monopoly in 21 seconds

Monopoly has a notorious reputation for lasting an eternity, but what if I said you could win the entire thing in just 21 seconds? According to Daniel J. Myers, a professor of sociology at Notre Dame University, the shortest possible game of Monopoly between two players requires just four turns, nine rolls of the dice, and 21 seconds.

In short, one player moves around the board very quickly to buy Boardwalk and Park Place, and places houses on them. Meanwhile, the other player ends up drawing a chance card that sends them to Boardwalk, and they don’t have enough money to pay rent with the three houses. Hence, the game is over.

Shortest Possible Game of Monopoly by profdjm

However, this particular game is incredibly hard to come by. In fact, Josh Whitford, an assistant professor of sociology at Columbia University, estimates that it would only happen once every 253,899,891,671,040 games, and who has enough time to play Monopoly that many times? But Myers and his son dedicated a significant amount of time to figuring out how to play the fastest game of Monopoly ever, and they’re confident this is the answer. You'll probably have to take their word for it!

Why going to jail is actually a good idea

Here’s another shocking Monopoly truth that’ll have you questioning your current strategy: going to jail might just be a winning move.

Jail is one of the most-landed on spaces on a standard board, and when you wind up there, you’ll likely find yourself itching to get back out again. But according to Natalie Fitzsimons, a UK Monopoly Champion, spending more time in jail could be the key to success.

Hailing from Northern Ireland, the 26-year-old was ranked sixth in the world when she beat her husband and three others to the UK and Ireland championship title back in 2015. When the game is just getting started, Fitzsimons agrees that its best to try and get out of jail as quickly as possible; after all, you don’t want to miss the opportunity to buy up property while it’s still available.

But in the latter half of the game, when all of the property squares have gone, there’s no shame in hiding behind bars. While you wait patiently for good old Officer Mallory to release you, you can still collect without having to cough up after landing on expensive property. It may not be the most exciting way to win, but, according to Fitzsimons, it might be the most effective!

How long was the longest game of Monopoly ever?

Let’s face it, Monopoly often feels like it might drag on forever. By the time you’ve reached the end, the sun has gone down, and you can hardly remember why you decided to play in the first place.

You may feel like you’ve already played the most time-consuming game of Monopoly ever, but the longest recorded game in history, according to Hasbro, actually lasted a grand total of 70 straight days, dragging on for an immense 1,680 hours! There’s no word on where or when the game was played, or who even took part, but it’s safe to assume they were nothing more than a pile of flaming ashes in their chairs by the end of it!

Monopoly Game for 70 straight days

You can’t imagine anyone wanting to try and beat that record, but of course plenty of people have! In Scranton, Philadelphia on March 13th, 1975, friends David Monteith, Lazlo Farkas, Mike Dux and Al Henderson sat down to a game of Monopoly that lasted 54 straight hours.

That’s right, they played all day and all night until they finally called time on March 15th. The only additional rule they added was unlimited borrowing from the bank to ensure that no one went completely bankrupt throughout the game.

An officiator, Bernadine Yencho, was present to witness the event, and a designated form was signed by witnesses each hour of the game. Jokes about Monopoly’s time-consuming nature have gone on for so long that, in 2019, Hasbro decided to troll us all by releasing a longest game ever version! Would you dare to play?

What is the world’s most expensive Monopoly set?

Monopoly isn’t known for costing a total bomb, but with over a thousand variations of the game worldwide prices do vary. You may think you’re shelling out for the newest themed edition, but how does a set worth a staggering $2million sound?

With a price tag like that, you’re probably thinking “It must be made of solid gold or something,” and you’d be right! This incredible one-of-a-kind Monopoly set was created back in 1978 by world-famous San Francisco-based Jeweler Sidney Mobell.

The board itself is made from 23 carat gold, while rubies and sapphires top the chimneys of the solid-gold houses and hotels, and the dice have 42 full-cut diamonds for spots. All things considered, it wouldn’t be surprising if you play with real bank notes, too, but they’re just gold paper!

When Mobell created the board, an ounce of gold cost between $360-$460, but nowadays the price of gold per ounce has topped $1800! The only time this game was played was in a showdown between Mobell himself and Britain’s former Prime Minister Edward Heath.

When the board was bought to London, Mobell was surrounded by armed guards! The set is owned by the Smithsonian and has never been put up for sale, which is a shame, imagine the satisfaction of flipping this thing in anger!

I hope you were amazed at these crazy secrets about Monopoly! Thanks for reading.