Randomized Auction Monopoly
Or, Monopoly without Monopoly
I grew up enjoying Monopoly. Yes, probably because I usually won. But the diplomacy of organizing trades was also deeply exciting for me. What kinds of trades could be made? You give me a monopoly, and I don’t charge you when you land on it? Permanently, or just the first few times? What happens if I’m bankrupted and someone else gets the Monopoly you’re immune to? Surely they aren’t obligated to maintain our arrangement. But what if I trade the whole thing to someone else, laundering out your immunity, in exchange for someone else’s? These kinds of questions were of great interest to me.
So I have Monopoly shaped grooves in my brain, perhaps disproportionate to how good a game it really is. I’ve tinkered before with heatmaps of how likely a given space is to be landed on, and thought some about how I think the optimal Monopoly bot would behave.1
But while Monopoly theory is fun for me, piggybacking off the joy I felt playing in my younger years, actually sitting through an entire Monopoly game is rarely a winning proposition.2 There are such better board games for the same time investment, after all. Thus, I also have an interest in another theoretical Monopoly question: how can you salvage the game? What is the best way, of all ways, to enjoy this gaming classic?
The answer, dear readers, may shock you.
The Randomized Auction
One problem with Monopoly is that the first hour or more is just rolling dice and mindlessly buying stuff. A good player should buy more or less anything they land on, and not that many trades tend to happen early on.
Luckily, this problem has an easy solution: start every player with the usual $1500, and shuffle the deck of properties. Then, one at a time - with nobody knowing the order ahead of time - auction off every property. Suddenly, while there is still enticing randomness (you could buy Boardwalk as the first property up, for example, then wait for Park Place only to find it last in the stack), players have more control over their destinies. Gone are turns where you land on someone’s owned St. Charles Place and fork over $12, or whatever. After the auction phase, all properties are owned, savvy bidders have their monopolies to start developing, and the game can begin.
I confess, this part wasn’t my idea. I forget who exactly turned me onto it, but it was someone in college, which such experimentation is at its glorious peak. And indeed - they were exactly right! Auctioning all the properties off at the beginning is clearly best. And for added fun, you can even change up the auction style; for any kind of auction, you could give it a try. For instance, once in college I played a game where all players bid simultaneously, and the highest bidder paid the second highest bidder’s price. The sky’s the limit!
So are we done? Not quite.
The Simulation
It’s perfectly acceptable to just play Monopoly, once all the properties are auctioned off. Why not? You’ve cut the game’s time considerably, and tilted the balance toward skill and away from luck.
But I propose something else. Because the act of rolling the dice, moving around at random, sometimes landing on an opponent’s hotel and sometimes not… isn’t it a bit too up to chance? Who among us hasn’t wondered, if we replayed the game 100 or 1000 times, how many times our specific portfolio of properties would have won the day? And indeed, after the auction phase, there’s little need for trading; players have already implicitly negotiated their ways into the best positions they can.
So why have the humans play one game robotically, when robots could play 1000 games, and see whose portfolio wins the most often?
Simulating Monopoly is tricky, but some other people have made simulators, so I’ve been tinkering with actually implementing this version of the game. Where all properties are auctioned off at random, and then bots take over, playing a huge number of games behind the scenes to see who made the savviest buys. My dream version of this software would actually have two winners: all players would predict the distribution of wins between the auction phase and the simulation phase. The first winner is the one who won the most of the simulated games, the second the one who made the closest guess for whose position was strongest.
Anyway, if I ever finish the project, I’ll link it on this blog. But for those who ever enjoyed Monopoly, the plain old non-simulated auction version is worth a try. It’s fun!
Mortgage everything but properties that can be Monopolies as soon as houses can be built, in order to get 3 on every property as soon as possible, for one.
Or, well, fine. I still do love plain old Monopoly. There’s something lovely about the little pieces, being a Shoe or Car and owning Marvin Gardens and going to Jail because you rolled doubles too many times. But you can only return to that well so many times, absent the gentle pleasant fog of nostalgia.

