The Top 11 Classic Monopoly Player Tokens – Part One

Which player token should you use?  No choice in the game of Monopoly is more crucial than this one.  The pawn you represent yourself with tells other players who you are, and what kind of strategy you will employ to seek victory.  Choose poorly, and other players will greet your trades with skepticism and scorn.  Choose wisely, and your play group will seek to trade commodities with you for little more than a smile.  Choose The Thimble, and the other players will snarl, snatching the game pieces back, slamming the box lid shut and insisting that you leave.

This top list is for The Classic Monopoly game, only.  I refuse to list and examine every permutation of every Monopoly game and game variant’s token.  So that means we will pretend that Monopoly didn’t have three tokens pulled from the core game in 1950 (A Lantern, A Purse and A Rocking Horse).  We’re also unimpressed with the Koala that only appears in Australian versions, the Locomotive, which only appeared in the Deluxe Edition, or the token remakes for Monopoly: Here and Now.    We’re also not here to discuss which of the Ninja Turtles was the greatest (That would be Donatello), or who is the most awesome character hanging out at the G.I. Joe home base (That was a trick question.  The answer is: Zartan in disguise).  Back in my day, we used to have eleven player tokens, and they were not created equal.

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Number 11: The Thimble

The Thimble is the lowest of the low.  If someone you don’t like asks you to play a game of Monopoly, there’s no better way to insult them than to say, “Sure!  I’ll take ‘The Thimble!'”  You could grab the box out of their hands, rip it in half, toss both halves out the window, punch that jerk in the face, then storm out of his building.  But if you did that, the hated gamer might sit down, confused by your actions.  By claiming ‘The Thimble’, however, you’ve sent a clear message:  I don’t respect you as a human being.

What makes this lowly icon so despicable?  To start, the thimble is a symbol of domestically.  It indicates someone who is happier darning socks than drinking scotch with the high rollers on a Saturday night.  Some would defend The Thimble based on its symbolic message of practicality, and frugality.  Beware those sniveling blackguards;  they only mean to lead you into a role of passivity.  No one wins the game of Monopoly by being frugal.  Daring plays and informed decisions will lead you to victory in this game.  That, and a clear mean streak meant to rob your fellow players from what is rightfully theirs.  A conversation between two Monopoly winners, meeting each other for the first time, might go like this:

Lex Luther:  So, you play Monopoly, too? Excellent.  You know, I’ve often enjoy playing the game as ‘The Thimble’, since it reminds me to take my time, and helps shape an environment of fairness that permeates to all of the players.”

Tony Stark:  True!  I believe it was Benjamin Franklin who said to “Beware of little expenses; a small leak will sink a great ship.”

Lex Luther [Through gritted teeth]:  Indeed.  Shall I see you in The Champagne Room in The Palm at eight tomorrow morning for a game?

Tony Stark:  Make it fifteen minutes of.  [Then, turning away, while speaking into his earpiece]  Miss Potts?  Cancel my appointments for the next two days.  I’ve met a master.

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Number Ten: The Iron

Another symbol of domestic living, The Iron shares many poor qualities with The Thimble.  It is, however, saved by the notion that The Iron is a symbol of eagerness.  While it infers simple beginnings, The Iron also proclaims that, while its owners may be humble enough to press their own clothes, they are fierce competitors who straighten their wardrobe and prepare themselves for the day that they will stride out on top of the world.

Iron players also get to stick a few puns in as they march around the board.  If you’re on a ‘hot streak’, you can roll the dice and announce that you’re “ssssizzlin!”  Extra bonus points are awarded to ironmen and ironwomen who ‘flatten’ their opposition, and it’s true that The Iron is an automatic trump for The Top Hat.  If you are unlucky enough to have The Top Hat while an opponent has The Iron, you should play in mortal fear of that opponent.  They may act charming throughout the game, but their sole desire is to crumple you into a crude burnt mess.

But for all of The Iron’s posturing, they’re still a ham-and-egger.  They’re the employee who wakes up in the morning, and wishes big thoughts while they toss the iron on the stove next to the frying pan.  True, you shouldn’t let your staff walk all over you, but the hot dog vendor on the sidewalk represents a more dangerous threat to your city-wide corporate takeover than an obsessive, lint-picking, fashionista.

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Number Nine: The Top Hat

We’re moving up in the world.  The Top Hat is a symbol of status and power.  Well, except for the time period that Monopoly is supposed to be set in.  While the top hat often became a symbol of wealth in political cartoons in the thirties, it was a tad unfashionable.  Certainly, important bankers and heads of state still wore them.  So did hobos.  If you’re playing the game of Monopoly and you happen to be the banker, then you’re probably fine.  If you aren’t the banker, however… let’s just say that if someone hands you a dollar bill while they pass by in the street, it isn’t a side effect of your magnetic personality.

To add to the the disgrace of playing The Top Hat, there isn’t a lot you can do with it.  How do you move around the board?  In a puff of magical air?  Any number of other icons can maul you as they smash their way across the strip.  Well, except for The Thimble.  You can drop down and own that piece.  But if your goal in Monopoly is to destroy the worst piece in the game, you won’t be putting The Ritz on any time soon.

Listen, we know what you’re thinking Top Hatters.  You’re thinking that by donning a bit of class that you’ll be transformed into Rich Uncle Pennybags in a shower of sparkles.  It isn’t going to happen, though.  Every time you flip over a Community Chest, or Chance card, Pennybags will be dancing in a shower of money there, while you hang out in a bar on Oriental Ave.  You will never live up to the legacy of your uncle.  Throw that hat away, and become a new man!  Embrace modern industry!  Or, you can ride the trains in your ratty old hat.  It’s your choice.

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Number Eight: The Ship

I have a high respect for players who choose modes of transportation to represent themselves in a game of Monopoly, I really do.  But, listen, Mack, you’re going about this all wrong.  This is Atlantic City we’re marching about, not  Atlantis.  You can try to drive your ironclad down the road, but without, um, wheels, you won’t be accruing deeds so much as piling up traffic violations.

I think I know what happened here, though.  You heard that Monopoly was all about big money and captains of industry, and you’ve heard the crazy sort of people those eccentric philanthropists become.  You want to be one the beautiful people; the sort of person who joins together a sled team of Scottish Terriers and rides it through the center of town while spraying citizens with diamond bullets.  But the difference between that mad billionaire and you is that that man came up with a workable, albeit absurd, idea, and put it to use mollifying the public.  For years to come, people will talk about how Uncle Pennybags flew a hot air balloon, fueled by his own money, from Jersey to New Jersey on a one dollar bet.  You have a boat.  You can either leave it at the docks and play the game, or you can tear it and the city to pieces as you hammer your round ship down a square street.  The whole point behind doing crazy things is for the mad respect, and you, sir, are losing it by the nautical yard.

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Number Seven: The Wheelbarrow

Okay, I admit it.  I have no idea what the hell The Wheelbarrow is up to.  Is this person planning on having so much cash, that they will need to cart it around in one of these?  I don’t know, but the wheelbarrow is empty right now, so we haven’t gotten to that stage of the game.  Still, I like this player’s panache.  They’re thinking about the future.  A future that involves a wheelbarrow full of money.  At least that future makes more sense than whatever Mr. Ship had planned up there.

Until then, I guess they’re just having fun pushing a wheelbarrow around town.  Maybe they give rides to other people for a little money.  Maybe they take that money and give it to other people so they can now be pushed around.  Are they working, or playing, or are they playing you?  I don’t know.  I do know, however, that a ride in a wheelbarrow requires two people, while winning Monopoly requires throwing away every friendship you ever cared for.  Maybe, in the end, the winner will be The Wheelbarrow, with a giant pile of money in it and a circle of armed guards.  But there will be no one to push The Wheelbarrow along through old age.  No one but one of the endless drift of gaping plebeian faces that line the street.  Oh, all alone!  All alone!

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We’re down five and have six to go.  Who will take the most beloved prize of best Monopoly piece ever?  Not The Boot.  That comes in fifth.  I’m sorry to disappoint you boot aficionados out there.  I just didn’t want to get your hopes up.  I know it must be tough to support a piece of footwear as best piece ever, and I’m just another disappointment in your quest to have The Boot recognized as the best piece of all time.  But, no.  It isn’t even in the top three.