Despite what your friends may claim, the key to putting the smack down in this classic board game is not the speedy acquisition of Boardwalk and Park Place, nor is it domination of the utilities or possession of the railroads—indeed, ownership means little in Monopoly. Instead, victory depends on your ability to choose wisely your game piece, or token. With the appropriate token working for you, in no time you’ll be thrashing your opponents.

One of the best tokens, hands down, is the cannon, because when others land on the same square as you, you can kill them with it. Even more dangerous and effective is the cannon-battleship combo, formed by soldering the two curios together. With this piece, you may fire lethal shots across the game board, provided opponents are residing on a property (i.e., not on a “Chance” or “Community Chest” square). The cannon-battleship may be fired only after rolling a seven, a ten, or snake eyes. Ammo is limited to five rounds, but additional rounds may be purchased for $50 each.

This amalgamated-weapon piece, while fairly superior, is still vulnerable, and finds a common enemy in the Scottie dog, whom, after years of protest by PETA, Parker Brothers has declared immune to gunfire. The Scottish-terrier piece possesses surprising agility despite its metallic nature, and carries with it another distinct advantage in that it can annoy any other game piece to death. It has long been a favored token among professionals and dilettantes alike.

Some players contend the speediest way to victory is, not surprisingly, speed. To this end, the best tokens are, from most to least effective: the train, the car, the horse and buggy, and the dog—the idea being that the train is a faster mode of transportation than the car, etc., and will obviously get you around the board more quickly. The dog-train combo is just as fast, and as a bonus will make you invincible to the cannon-battleship. Some contend the battleship, by itself, is faster than the car, and possibly even faster than the train. But remember: you are on land. A nautical vessel doesn’t really make much sense for terrestrial transport. You’d be better off trying to scoot along in the thimble.

The iron is a worthless token that should only be used by domestic servants and children who don’t know any better. The top hat, though it did wonders for Abe Lincoln and Fred Astaire, is also among the weaker game tokens. It becomes slightly more powerful when carrying the dog (affecting an air of “magic”), or sitting upon the head of the speeding buggy driver. But without cane and tap-shoe accompaniments, the top hat ultimately falls short. The boot, symbolically, is rather base in light of the goal you are trying to accomplish, while the bag of money (available in later editions) seems conversely presumptuous. Combinations that include any of these weaker tokens will have dubious strength, not to mention a quite silly appearance.

What, though, of the wheelbarrow, a longtime favorite? This piece might look good at first glance: it is mobile, after all, and nicely houses the terrier in the dog-barrow combo. Yet experience shows that, for all its seeming usefulness and salt-of-the-earth implications, this burdensome tumbrel will only hinder your quest for capitalistic domination. You could learn the hard way with this token, or you could simply heed the words of William Carlos Williams, whose 1951 poem “The Silver Wheelbarrow” immortalized the game piece in all its flawed glory:

so much depends

a silver wheel

although not really,

the silver wheelbarrow is
a piece of shit.