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Published: Mar 17, 2017 12 min read
boot monopoly token
Malcolm Park—Alamy

When we were kids, my brother and I used to play Monopoly with my grandfather. He always picked the boot token. Not coincidentally (at least to us) he always lost.

My brother and I gravitated towards what we considered the “power” pieces. The top hat. The racecar. The cannon. The Scottie dog, which looked like it belonged on the lap of somebody powerful and affluent, who fed it caviare and called it “sweetums.”

But my grandfather always saw himself as the work boot. If he had a reason, he never came out and explained it. We never got a lecture on the symbolism of Monopoly tokens, or how by choosing the top hat we were buying into a culture of winner-take-all capitalism. He just preferred the boot.

He also played like somebody who wasn’t all that interested in bankrupting his family with real estate investments. Which is crazy, because that’s the whole point of Monopoly. That’s like playing Candyland and not caring if you get the Ice Cream Sea card. Do you even want to get to Candy Castle, dude?

But he never seemed to care. He rarely invested in real estate or utility companies, opting instead to hold onto his tiny fake money because he was “saving for the future.” When he did buy property, he declined to charge us rent when we landed on his space.

“You’re playing this wrong!” we’d scream at him.

He’d just shrug. “I’ll be fine,” he said, counting his increasingly small stacks of cash.

I never made the connection between my grandfather’s Monopoly strategy and his personal life. But it was there. He was a fiercely liberal Democrat who wrote angry letters to The Nation when he felt they were leaning too far to the middle. He was a high school teacher with a salary just slightly more than a 7-11 employee, a proud union man, and a home fixer-upper whose idea of a great weekend involved ripping out drywall. He was the closest to a living embodiment of a Monopoly shoe token that I’ve ever encountered.

I’ve never been able to play Monopoly without thinking of him, and feeling a little guilty when I don’t take the boot token. But that quandary is gone now, because the option of choosing that symbol is no longer on the table. As of today, the boot token is gone. Kaput. It sleeps with the fishes.

It all started this past January, when Hasbro—the toy-making behemoth that owns Monopoly—launched a campaign asking the public to vote on their favorite tokens for a new generation of the game. Four million people weighed in on 50 options, which included the classics, like the boot, top hat, and Scottie dog, and some amazingly awful new prospects, like a gramophone, monster truck, and bunny slippers.

The thimble will pass Go no longer.
NoDerog—Getty Images

Which is essentially like saying, what should be the emblem of the United States: The bald eagle, or a TMZ photo of Justin Bieber urinating in a restaurant mop bucket?

Seriously, Hasbro? A bunny slipper? That was an actual choice for an 82-year-old board game that we've all agreed without saying as much out loud is essentially capitalism role playing?

When the dust settled this morning, three tokens were gone —the boot, the thimble, and the wheelbarrow—and three new ones were introduced: a T-rex, a rubber ducky, and a penguin. Of course. Because nothing symbolizes the harsh reality of laissez faire economics like extinct reptiles, a child’s bath toy, and a waddling flightless bird.

If debating the “symbolism” of Monopoly tokens feels a little silly, you’d be right. But that doesn’t mean it’s not true. A cigar is sometimes just a cigar, to paraphrase Freud, but the miniature top hat in a board game about real estate and industrialism is absolutely an iconic Progressive Era financier.

“J.P. Morgan clearly inspired the creation of the game’s Monopoly Man character,” says Philip E. Orbanes, a board game designer and author of three books about Monopoly, including The Monopoly Companion. “His top hat was clearly seen as a symbol of wealth. The boot was, by contrast, representative of the working class.”

Hasbro more or less backs up this interpretation. Jonathan Berkowitz, a senior vice president of marketing for Hasbro Gaming, says the boot “was modeled after the working shoe of the 1930s, and we like to say that the top hat has been a staple in Mr. Monopoly’s wardrobe from the very beginning.” As for whether the tokens represent a class structure of extreme financial inequality, Berkowitz doesn’t offer much insight. “We enjoy the ‘folklore’ our fans have created around the iconic game,” he says.

Fans aren’t the only ones creating folklore in air quotes. The game’s official origin story is debatable, says journalist Mary Pilon, author of The Monopolists: Obsession, Fury, and the Scandal Behind the World's Favorite Board Game. “As Parker Brothers (the original creators of Monopoly) told the story for years and years and years, a man invented the game during the Great Depression while he was on the brink of destruction financially,” Pilon says. “He sells it to Parker Brothers, it becomes a huge hit and saves him and the company from ruin. It’s a great story, but it’s also not true.”

The game was actually created in 1904 by a Quaker woman named Lizzie Magie. She called it The Landlord’s Game, and it was intended to teach children about “the gross injustice of our present land system,” Pilon wrote, “and when they grow up, if they are allowed to develop naturally, the evil will soon be remedied.”

Long story short, a game that was passed around and played for over 30 years by Leftists nationwide was stolen by a toy-making empire who got rid of all the commie BS, and now the only “lesson” is that it can be super fun to build a fortune by destroying the nest eggs of your neighbors.

There’s so much irony in the history of Monopoly. It started as a game for the working class, then it became a game about class warfare, where the super rich (the top hats and their pampered dogs) were pitted against hard laborers (the boot, the thimble, the wheelbarrow). And now, with ”World Monopoly Day,” set for this Sunday, (as Hasbro calls it)—it’s officially a game where minimum wage earners don’t even have a token anymore. It’s all top hats and penguins. Hey, that penguin token looks like he’s in a comfortable tax bracket. He’s wearing a damn tux!

We like to brag that we live in a country where anybody can make their fortune with hard work and determination, but c’mon, we don’t really believe that. The guy in the work boots pushing the wheelbarrow is never going to become a megalomaniac billionaire who marries an eastern European model and has ties to the Russian government. But the guy with the top hat and the monocle, holding the adorable dog? He was born rich and he’ll die rich, and there’s not a damn thing you can do about it.

We elected a president who was born rich. On the Monopoly board, Donald Trump is the top hat. He’s not the work boots, and he’s definitely not the wheelbarrow or thimble. Donald Trump is our president for the same reasons that everybody wants to be the top hat when they’re playing Monopoly. The top hat is Mr. Monopoly. He’s got his freaking name right there ON THE GAME. Monopoly is his Trump Tower. You think he’s sweating it over whether the wheelbarrow is going to take an interest in real estate?

courtesy of Monopoly

I realize that I’m starting to sound like a stoned college kid who just read Manufacturing Consent. Obviously, none of this is systematic propaganda. It’s just a publicity stunt for an antiquated board game that needs a reason to stay relevant in a digital age. Nothing else going on here. But just to be safe, I reached out to Noam Chomsky, the pioneering linguist and MIT professor emeritus, and asked if getting rid of the Monopoly tokens that aren’t symbols of opulent wealth could be considered a nose-thumbing to the working class.

“The question that comes to my mind is whether people are even aware of the symbolism that you describe,” says Chomsky. “If not, then the ‘nose-thumbing to the working class’ is even a more impressive success in doctrinal management by those who Adam Smith called ‘the masters of mankind’.”

He’s referring to Adam “Father of Modern Economics” Smith, who wrote this in The Wealth of Nations (1776): “All for ourselves, and nothing for other people, seems, in every age of the world, to have been the vile maxim of the masters of mankind.”

“All for ourselves, and nothing for other people” is not the official slogan of Monopoly, but it might as well be. The official Monopoly slogan is “Own it all.” So, yes, Adam Smith nailed it. (Coincidentally, the now discontinued Trump board game—which is like Monopoly played with all top hats—featured the slogan: “It’s not whether you win or lose, but whether you win!”)

In the end, it doesn’t matter. It’s not like anybody plays Monopoly as a metaphor for our cultural relationship with wealth and power. We just want the fleeting endorphin rush of bankrupting friends and family. But still, little gestures matter. When my grandfather instinctively reached for the boot token, and then lost the game by not following the “Own it all” rules, it left an impression on me. Being a ruthless, remorseless oligarch isn’t as much fun if the other players are taking pleasure in being decent.

I’m going to try and do the same thing with my son. I likely won’t be as graceful a loser as my grandfather was, but maybe I can find a way to have a silent conversation with him about money. And why not? Everybody dreams of being a rich douchebag in a top hat. I’m going to make the rubber ducky my token of choice, because it reminds me of Sesame Street.

Yes, my symbol of economic striving is going to be the bathtime companion of lower middle class New York muppets, two single adult males who live together in a small one-bedroom apartment, which can get frustrating but New York rents have gotten insane, and they’re pretty sure they’re both going to lose their health insurance, but they’re not giving up because they know with just a little hard work and the kindness of friends, you can do okay in this world.

Yeah I know it’s stupid. I know my son is going to laugh at me, as he scoops up the last of my Monopoly money and sneers, “How’s that strategy working out for you, Ernie?” Well, whatever. Somebody’s got to keep this game honest.