Gambling on Monopoly is the Most Degenerate Thing I’ve Ever Done

Everyone learns the game of Monopoly from when they’re a little kid. It takes fucking forever, just hours and hours cause no one knows how to play it correctly, plus the regular rules are bullshit. Everyone’s gotten pissed, flipped the board over and quit. In fact, more people probably completely hate this game than people like it. But everyone’s played it.

Dane Cook even had a whole schtick about it back on his Harmful If Swallowed special back in 2003.

I hated Monopoly throughout the years. I couldn’t stand sitting there long enough to not get bored playing a board game. Plus, I hated doing all the math. So I would never play it. Fuck wasting like six hours to get pissed off at my brother for manipulating me with stupid trades to crush me at this game.

As an adult though, a friend of mine introduced me to a slightly modified version of the rules to speed up the game to around a half hour to an hour and I found a new appreciation of the game.

The modified rules are pretty simple:

  • You can’t buy any properties your first trip around the board (actually makes a stunning difference to the speed of the game for a rule so simple that seems meaningless).
  • Income tax and luxury tax, any fines paid from Chance and Community Chest cards and paying bail to get out of jail goes into the middle of the board, not the bank.
  • If you land on Free Parking, you get all the cash in the middle. The middle of the board starts with $500 on it from the bank. That decreases each time someone lands on it until its $100, which it stays at each following time. 
  • If you land on Go! (not pass it but actually land on it), you get $400 instead of $200. 
  • Everything else is the same

I regularly started playing it with these new rules, just to give me something to do. Games wouldn’t go longer than maybe an hour and a half maximum and once you learn the optimal ways to move properties around and stuff like that, it makes it even more fun. 

But just like everything else, after a while you get bored of doing the same thing. So what better way to enhance a game than to gamble on it. I told my buddy the idea to maybe play for five bucks every time we played (usually we crush two or three games in a couple hours while having some beers). As a fellow degenerate, he liked the idea and said, sure why not? Obviously, $5 isn’t much and eventually like anything else you starting doing the double or nothing game and then it becomes like $20 on a game of Monopoly, which ironically is what the whole board game costs.

Gambling on Monopoly is probably the most degenerate thing I’ve ever done. I’ve bet on European Tour and Korn Ferry Tour golf events. Even just dice rolls or coin flips and shit like that. Monopoly’s a game all about making other people go bankrupt while getting rich on other people’s failures. It’s pretty much all a metaphor for gambling. Don’t go broke and chase trying to get rich. Why not gamble on it? Gambling makes everything more fun.