I have never won a game of Monopoly.
I have, however, spent many hours helping other people finish winning one.
This is partly an essay about what makes a game worth playing. Mostly, it is a rant about why Monopoly makes losing take so fucking long.
There is always a point when the game is effectively over. One player has reached critical mass. They own half the board, everyone else is mortgaging whatever remains, and no plausible sequence of decisions will change the result.
Then Monopoly continues for another hour.
Perhaps winning feels better. I wouldn't know. I imagine there is some satisfaction in grinding your friends into bankruptcy. Not too much satisfaction. Just enough to make their suffering worthwhile.
But surely even the winner eventually wants the game to acknowledge what everyone around the table already knows.
Monopoly usually ends long before it stops.
At first glance, Monopoly's problem seems obvious: luck. You roll the dice, land somewhere, and accept whatever the board has decided to do to you. But I love games with luck. Magic: The Gathering is probably my favourite game ever made, and it begins by shuffling your carefully constructed deck into an order you cannot control.
Luck isn't the problem.
The problem is being offered the performance of a decision when there is barely a decision to make.
You land on an unowned property. Do you buy it? Most of the time, obviously, yes. If you repeatedly refuse without a strategic reason, you aren't expressing an alternative play style. You're griefing. You are the League of Legends player running directly into the enemy team while insisting that experimentation is part of the game.
This is not quite as simple as I wanted it to be. Under the official rules, declining a property triggers an auction in which every player, including you, can bid. Monopoly also has trading, building, mortgaging, cash management, and decisions about leaving jail. There are better and worse properties. There are better and worse players.
To my frustration, under the formal definition used in game theory, Monopoly is unquestionably a game. It has players, strategies, payoffs, and outcomes that depend on what everyone else does. A game does not stop being a game because it contains luck or because rational players frequently arrive at the same decision.
So the dramatic version of my rant doesn't survive: Monopoly is a game.
It just spends far too much time making me feel like I'm not playing one.
Mark Rosewater, the head designer of Magic, once proposed that a game needs goals, restrictions, and, most importantly, agency. In his essay "What Is a Game?", he argues that a choice whose correct answer is always the same is not really a decision.
That distinction explains why Monopoly feels worse to me than Snakes and Ladders. Snakes and Ladders is honest. You roll the dice and watch the race happen. Monopoly surrounds the dice with money, deeds, auctions, and the appearance of economic control. It lets you touch the machinery while giving you surprisingly little power over where it goes.
Worse, the amount of power you have shrinks as you fall behind. The player with property earns rent. The rent buys more property and houses. Those properties produce more rent. Their decisions become increasingly powerful while yours become increasingly administrative: roll, move, pay, mortgage, repeat.
Chess has the opposite problem. Against someone much better than me, I will probably lose every game. There is no lucky draw coming to save me. But every move matters, the advantage was earned, and when the position becomes hopeless, I can resign. Chess has a graceful way to say that the meaningful game is over.
Monopoly doesn't. Not when played casually with friends, anyway.
You could get up and leave, but that feels petulant. Your friend deserves the satisfaction of winning properly. I also hate leaving things unfinished. So I stay at the table and help the game complete the administrative work of bankrupting me.
This is the strange social trap Monopoly creates. As a player, I know my meaningful participation is over. As a friend, I feel obliged to remain so somebody else's victory can feel complete.
The losers donate their time to the winner's conclusion.
Magic offers a different bargain. An opponent puts a threat on the table. Either I have an answer or I don't. If I don't, I can use the mechanics of my deck to search for one. I can draw more cards, preserve my life total, choose which resources to spend, and play towards the cards that could still save me.
Sometimes I find one. Sometimes I don't. Luck still decides plenty of games.
But the possibility of getting lucky creates decisions before the lucky card ever arrives. I am not merely hoping. I am identifying my outs and trying to reach them.
That is one of the things I want from a game: actionable hope.
I don't need every player to have an equal chance of winning until the final turn. I don't need a game to feel sorry for me and manufacture a comeback. I need it to keep giving me meaningful ways to pursue one. If the game continues after those ways have disappeared, it is no longer creating tension. It is producing captivity.
For a long time, I thought searching for an answer was the most interesting thing a game could let me do from behind.
Then I played a game that dared me to do something even stranger.
It let me make the entire world less stable until an answer became possible.
That game deserves its own essay. I'll save it for the next rant.