I think it was back in college when I first came to realize that Monopoly was a terrible game.
I had grown up playing it, of course, like any good red-blooded American. My family invented our own special house rules, like every family did. At one point I lost a game by landing on Ventnor Avenue, which was owned by my brother. He had improved it by building something like 5 or 6 hotels, which I'm almost sure is not technically allowed under the rules. When my wife and I started dating, we played sometimes and I learned the rules that she played with. It felt like a way to learn something about where she came from.
But I came to realize that the rules of Monopoly, as a game design system, are eye-bogglingly awful.
The only thing that matters to the outcome of the game, of course, is obtaining monopolies and improving them. There's no way to bankrupt your opponent by any other means. Railroads and utilities are meaningless past the early game. The cards matter not at all except in cases where they cause someone to land on an improved property. In the late game, landing in jail is actually a huge advantage, and your stints in the slammer to last as long as possible.
At one point I even undertook a project to rebalance the game to enable multiple paths to victory, and to smooth out the value on rents and property values so that the early game mattered as much as the late game. Yes, hanging around with me is a non-stop party. I abandoned this effort before too long, luckily, but the fact that I felt the need to undertake it at all says something. I've never tried to figure out how to rebalance Sorry, or Stratego, or Battleship.
I was blown away to discover later in life that the game we call Monopoly was, in its protean form, not supposed to be a fun or balanced game. It was designed to teach economic lessons about Georgist economic theory, which I only learned about by reading about the history of a board game. So, mission sort of accomplished? Eventually?
The game plays the way it does because it was meant to show the outsize economic power of owning land and having monopolies. It was never meant to be balanced.
I don't know about you, but I never felt like I learned any kind of lesson from playing the game as a kid, apart from the fact that my brother cheated, and that it was fun when you had a lot of money.
But the game obviously touched something in human nature to have gone viral in the way it did, quite beyond the plan or intent of its various creators. It was fun to acquire land, to amass wealth, to make trades and negotiate, even if the rules weren't totally optimized (I'm looking at you, "tally up your assets and pay a percentage as income tax").
The reason the game didn't teach the lesson it was meant to teach is built into its nature as a game. Each time you play, it's a fresh start, a fair deal. Every player starts with the same amount of cash, and there's a wide open real estate market just waiting to be scooped up.
To really illustrate the economics it was meant to illustrate, there would need to be a change to how Monopoly is played: make it a legacy game, where each session is shaped by what happened the last time you played. How much would you want to play Monopoly if every time you played, your opponent started with the property they'd built up the last time? Starting with the same amount of cash would not matter at all if your opponent had hotels at the beginning of the game. The board would be stacked against you, and it would only be a matter of time before you lost.
If Monopoly had been designed that way, it would have made its point much better. But of course it would never have gone viral in the first place, because no one would ever want to play a second time.
I get very skeptical whenever someone starts touting the virtues of an unfettered free market, and this is part of the reason: we are all living in a Monopoly game where there's no restarting, no clean slate. Accumulated wealth has a way of skewing the game. The rich have the means to make sure they keep getting richer, and all the poor can do is keep rolling the dice, hoping they land on Free Parking.