Real Cheaters Monopoly

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Who are your current most favorite people?

We were insulted, just insulted. They’ve got a special edition of Monopoly, now called Cheater’s Monopoly. That’s cheating! In the old days, we played with a standard game and “special” standard rules. Rules for cheating, that is. Mr Monopoly! You’re always one of my favorites out of the great multitude of cheating, selfish capitalists. But this is one step too far.

I would like to rush and assure you that real cheaters’ Monopoly started many years ago. My uncle, a Navy Gunner’s Mate, assured me that it was an ancient and noble Navy occupation during the Second World War. And I played during my time in the Navy.

Cheaters Monopoly – the basics

I was reminded of this by a close friend who called, and the conversation came around to games. Almost simultaneously, we former Navy guys hollered out, “Cheaters Monopoly!” The basic overriding rule was that what you could get away with worked, but if you were caught, you went to jail. No get out of jail free card? You paid cash on the barrelhead depending on the roll of the dice. It was an exciting game. You could win big or lose bigger.

Now, every once in a while, someone got really pissed and a board got tossed. If all the pieces could not be retrieved, you were responsible for replacing the game with a new one. Sounds a bit onerous, right? Well, some of those missing pieces, money, chance cards, and such found their way into a cheater’s stash of goodies. It was no accident! A get out of jail free card was always a high-value item, as was a card with Mr. Monopoly advancing to collect two hundred dollars. We played in the berthing area, and pieces could “go missing” but get secretly retrieved.

Having cut my Monopoly “teeth” as a kid playing against my “anything goes, rules be damned” sister. I was not too bad at this. On one cruise, I played almost nightly against PO1 (first class petty officer) John O’Toole. O’Toole masterminded the bootleg hooch racket. Our side bet was a fifth of bourbon, and I took his prize token, the little Monopoly battleship. I did so well on that cruise that after a while I had trouble finding opponents.

Don’t believe me? Here’s my little flotilla of battleships won from O’Toole. I keep them as a reminder of good times. The multitude of bourbon bottles was shared with shipmates.

A collection of silver Monopoly battleship game pieces displayed on a wooden surface.

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8 Replies to “Real Cheaters Monopoly”

  1. Great story! I had never heard of Cheaters Monopoly. Games in the military just makes me think of Spades. I had never heard of it before the Air Force, but while enlisted, played around 11 million games of it, haha.

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