Why You Can’t Cheat at Cheat Monopoly

A few years ago I learned how to play Cheat Monopoly. It’s a great game, if you’ve never played, and I highly suggest it. But fair warning- only play with people that you’re close enough to that you’re comfortable with their humor and will not butt heads.

I can promise you that will happen regardless. This is not a game that you want to play with new friends, people who hold grudges, anger easily, or as I found out, your sister.

The Rules

The object of the game is the same as regular Monopoly, except you cheat as cleverly and as much as you can. You steal money or property, move extra spaces, or do anything that you can get away with; as long as you don’t get caught within two turns. After two turns you are free to boast about how much money you stole from someone or whatever it was that you did. If you do get caught, you have to give up what you stole and put two hundred dollars in the center, and if you wrongly accuse you have to put two hundred dollars in the center too.

The game gets vicious fast. You’re always suspicious of the banker and the realtor, who, if we’re being honest, are both most likely guilty. You have to watch every player with a hawk’s eye while simultaneously try to fly under the radar yourself. If you get paranoid or anxious easily, this isn’t a good game to play. The amount of tension in the room is comparable to high stakes poker. Playing regular monopoly can take about one to three hours to completely finish. Cheat monopoly on the other hand is less predictable. Depending on the stealth and skill of the players, it can take anywhere from a half hour to twelve hours.

It will put your friendships, patience, and awareness to the test. And don’t even think about stepping away from the board. Never underestimate or trust the other players.

The Lesson

That was a lesson that I taught my sister the hard way. We decided to play in my living room one day with her boyfriend at the time. It was my job to set up the board and get everything ready while they were in the kitchen making food. The first and only rule of Cheat Monopoly is cheat as much as possible without getting caught, so of course I hid the best properties and about one thousand dollars under my seat while setting up. It was the perfect cover, they were busy making popcorn and I had all the cards and money at my fingertips.

We started the game staring each other in the eyes, watching every move. All three of us were relatively good at the game. We all had moments where we were sweating just waiting for someone to call us out and rubbing it in the others’ faces when we didn’t get caught. And then my sister landed on one of the most expensive properties (one of the dark blue ones). I smirked as she looked through the remaining properties, knowing that I was literally sitting on that one.

I stood up and grabbed the pile of money and properties that I was hiding since the beginning and pridefully explained how I stashed them before they came into the living room and have been waiting for someone to land on them. Her boyfriend laughed and gave me a high five, thinking it was clever, and made a comment about how they shouldn’t have left me alone with the board.

My sister however, did not appreciate it as much. In fact, she became furious because I cheated (at Cheat Monopoly) before anyone else was in the room. She scolded me for doing so and demanded I give the property up. I admit that I didn’t take it as well as I could have, and we started arguing over it. We’re both pretty stubborn; it got to the point where we stopped playing because I refused to give up what I stole and she refused to be okay with it and continue to play.

If I remember correctly, it ruined the day because we stayed mad at each other for the rest of it. I don’t think she has played Cheat Monopoly since that game. As stressful and potentially cutthroat the game is, it’s still fun. I hate knowing that a disagreement between us is the only reason that she doesn’t like the game anymore. At the time, in my eyes, I was correct. But I know at the same time, through her eyes, she was the one who was correct. I wish now that I would have sacrificed my pride, given up what I took, and played by someone else’s rules beside my own. Looking back, I know it was wrong of me to expect everyone to play by the same set of rules that I had in my head and not be open-minded to others.

You can’t cheat at Cheat Monopoly.