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The Story Behind Each of the Most Popular Monopoly Pieces, Past and Present

The Story Behind Each of the Most Popular Monopoly Pieces, Past and Present

While many board games use colorful little pegs as markers, Monopoly, the game with the unique power to unite and divide a family in the matter of an hour, has those odd tokens you’re no doubt familiar with. You’ve probably played more than a few games with the little racecar or thimble without ever stopping to think, “Why the hell am I a thimble?”

Monopoly was created by Lizzy Magie in the early 1900s as a way to demonstrate, in game form, the greedy land grabbing that robber barons were doing in the Gilded Age. It was about as anticapitalist a game as they come — until a greedy capitalist of another sort came through and changed that. In the 1930s, Charles Darrow took credit for the idea of the game and put forth a story about using small items from around the home as playing pieces. He continued to get credit for Monopoly’s creation for more than half a century until people started to shed light on Magie’s true story in the 2010s.

While the origin story has more than its fair share of unfair plot twists, the original version of the game itself has been consistently popular with a long line of special editions with unique pieces. From 1950 to 1988, the pieces stayed the same. A lot has changed since then, though. These are the backstories of each of the major pieces.



Top Hat

Often considered the most recognizable icon of the game, the top hat is one of the things you might expect a Gilded Age railroad titan to wear. The token was based on the hat the game’s lead character, Mr. Monopoly, would wear. Of course, when the game was introduced, he was known as Rich Uncle Pennybags, and many have speculated the character was based on J.P. Morgan.



The piece of choice of US Monopoly champion Richard Marinaccio, the thimble is one of the original pieces. Much like the top hat and shoe, the thimble has appeared in most versions of the game that have been released. It didn’t make it far into the 21st century, though. The thimble was retired in 2017, only to make a surprise comeback in 2022.


Iron (Retired)

The iron was another classic token that fell to the wayside. Perhaps saddest to see it go was Monopoly World Champion Bjorn Halvard Knappskog, who used the piece in his last championship match. The iron should have seen the writing on the wall: it was the second least popular piece in a 1998 vote.


Boot (Retired)

Around since the beginning, the Boot was modeled after the practical work shoe of the 30s. Instead of changing its design with the times, the Boot has remained the same and is a symbol of both hard work and the riches that can come along with it. It was the third and final token to be retired in 2017. A T-Rex, penguin, and rubber ducky replaced the thimble, wheelbarrow, and boot.


Battleship (Retired)

The die-cast metal battleship token is actually somewhat of a game piece celebrity. The piece was originally used by Parker Brothers in a game called Conflict. When that game failed, it was easy enough for the company to take the pieces and use them in Monopoly. Since then, it has also been used in the game Diplomacy as well.


Cannon (Retired)

Often called the cannon even though rumor is the piece was supposed to be called the howitzer, this piece is closely tied to the battleship.The cannon was also used in Conflict and tossed in with Monopoly as that game failed. In 1946, it changed from its original design to the long cannon style. Unlike most pieces, the cannon was simply dropped from the lineup without any kind of fan vote or campaign. Some might say heavy artillery doesn’t belong in real estate, anyway.



The car was the seventh token added to the original game. The racecar steals its sharp looks from a 1930s roadster. The original idea was to design the car token based on the car Mr. Monopoly would drive around. It’s undergone a few changes through time, and it sported a “3” on its side until sometime in the 1960s.


Purse (Retired)

The purse became the eighth playing piece to join the Monopoly family, and it has a bit of an odd history. It appeared and disappeared from sets beginning in 1935 or 1936 until it was finally retired in the early 50s. Early on, the game pushed the limits expanding to 10 tokens (the purse being one of them) and then scaled back and continued to oscillate this way for years. The purse seemed to be thusly added and removed as these changes occurred. Photo Source


Rocking Horse (Retired)

The rocking horse is one of the more hard to find pieces nowadays, and screams pure nostalgia. It was only around from the 30s to the 50s, and it didn’t appear in many editions of the game during that time. Photo Source


Lantern (Retired)

The lantern is tied at the hip with the rocking horse. Both were added at the same time and removed in the 50s when the Scottie dog, the wheelbarrow, and the horse and rider were added. Photo Source


Scottie Dog

One of three new tokens added in the 1950s, the Scottie Dog became Mr. Monopoly’s right hand pup. The token has become the most loved of all the pieces. Who wouldn’t want man’s best friend by their side as they buy up Illinois Avenue?


Wheelbarrow (Retired)

Introduced in the 1950s wave of token changes, the wheelbarrow was one of the pieces that replaced the lantern, purse, and rocking horse. The wheelbarrow was included as an emblem of hard work and one of the prime tools needed to build the properties around the board. It met its demise in 2017 with the thimble and boot.


Horse & Rider (Retired)

The horse and rider became a staple piece beginning in the early 50s until it met a similar fate as the cannon of being removed without much fanfare. Cars, apparently, are much more in vogue.



Sack of Money (Retired)

The sack of money became the first new token added in over 40 years in 1999. It beat out the piggy bank (20 percent of the vote) and the bi-plane (29 percent of the vote) with 51 percent of a 1.5 million person poll Hasbro ran. Unfortunately for the sack of money, it was retired less than a decade after it was introduced.



The winner of a recent vote, the cat is one of the newest piece you’ll find. The cat defeated the diamond ring, a guitar, a toy robot, and the helicopter to find itself among the lot.




The Tyrannosaurus Rex token received more votes than any new potential game piece in the January 2017 vote for new pieces. By May of 2022, Hasbro announced it would “head to extinction” in a twist of fate that saw the return of the thimble.

Rubber Ducky

Rubber Ducky

Ushered in in 2017, the rubber ducky has thus far survived the whims of Monopoly fans.



Another piece that was brought in in 2017, the penguin lives on to this day.

Top image by All Vintage Man