Breaking Monopoly

What if the classic board game had better rules for simulating capitalism?

Every year, when the temperature in New York dips past freezing, my friends and I vote against catching hypothermia on a subway platform, and make plans to play Monopoly. It is a perfect game when you are forced to sit somewhere for a very long time, because there is no game clock, and no easy way to speed up the proceedings. We have never played a game that finished in fewer than five hours and like all games, it reveals the secret heart of the people you love, as they are free to pursue complete victory without the usual factors of empathy, laziness, absent-mindedness, etc. impeding their ascent in real life. More specifically than other games, it also makes you think about capitalism, and the ways in which you’ll never be happy.

Monopoly was invented in 1903 by the fiercely progressive Elizabeth Magie, who designed it as a warning against prominent monopolists of the era like Andrew Carnegie and John Rockefeller. She created the game, then called The Landlord’s Game, with two sets of rules: Players could win by achieving wealth for all, or they could win by crushing their opponents and assuming all the money for themselves. Perhaps not surprisingly, the latter was more popular. Her idea was copied by a man named Charles Darrow, who sold it to the Parker Brothers gaming company, whereby the rules were modified and the name was changed to Monopoly.

Soon after its release in 1935, it became a hit. Amongst the iconic board games — Scrabble, chess, backgammon, and so on — Monopoly is unique for the way it streamlines and miniaturizes the dynamics that rule us in real life. In America, we are meant to accumulate wealth and property, and the elements enabling our success can be as random as a roll of the dice. (Think of one’s rich parents as the equivalent of landing on Boardwalk and Park Place.) Monopoly is the American Dream, shrunk to a tabletop.

While playing, I find myself increasingly unable to separate my in-game emotional state from my real one. When I struggle to buy property and collect pricier rents, when my dice take me into dangerous territory, when my deals backfire because of some variable I haven’t considered, I become unusually upset and irritable. I project myself into a future where I am left with a faltering business, an empty bank account, and insurmountable debts. Winning in Monopoly requires some reserve of tactical acumen, but it’s really just about how lucky you get when moving around the board. Make too many poor rolls and it’s incredibly difficult to recover, and when this happenstance misfortune leads to my downfall, I consider how easy it would be for the same to happen in real life.

During a January blizzard, my friends and I settled in for a long night. I did not begin the game particularly successfully, and irritated with the prospect of going to pauper’s jail, I made a spontaneous attempt to bend the rules by offering real money during a prospective deal: St. Charles, $200 of in-game money, and $20 of American money to secure Illinois, which would allow me to achieve a monopoly and begin building. ($20 was a lot, yes, but I’d had a couple of drinks, and was feeling frisky.)

My opponent immediately said yes, because she realized we were playing a children’s game. But everyone else at the table protested, since it would benefit me, and because they did not want to have to consider spending actual money in future deals. (I futilely attempted to cite the Air Bud corollary, which states that there’s nothing in the rule book that says a dog can’t play basketball.) The deal was rejected, and unsurprisingly, I ended up losing altogether.

At home, I couldn’t stop thinking about my failed attempt to rewrite the rules. Why shouldn’t real money have been allowed? We were simulating capitalism, and in capitalism, you throw whatever money you have to get what you want. Allowing me to shell out cash to sweeten the deal wouldn’t have just allowed me to succeed in the game; it actually would’ve been truer to the ideological premise.

I didn’t stop there. I wondered what other rules could be introduced in order to better simulate the dynamics of capitalism, without fundamentally ruining the core Monopoly experience. It should be easier to achieve what we wanted, I thought, both in the game and in life.

After some brainstorming, I settled on a loose set of additions to the rule book.

First, real money would be allowed into the game, but only as part of a deal for property. The concept of mergers would be formalized — this had also been shot down during the other game — allowing two struggling teams to join forces, and achieve some sort of compromised victory. (The true monopolist seeks to dominate on his own.)

Running out of money can be a frequent issue, stretching games to interminable lengths as players wait to pass Go and accumulate rent. A loan system, requiring diligent bookkeeping from the banker, was necessary. But how would you simulate the risk of taking out real loans? While window shopping in a tabletop game store, I came across a wall of multi-sided dice, and had my answer. Upon requesting a loan, players would roll a 20-sided die — most commonly used in games like Dungeons & Dragons — and multiply it by 10. That number would be the percentage of interest charged if the loan was failed to be repaid inside two turns around the board.

The incorporation of the d20 allowed for all kinds of probability-based additions. I devised a scenario for a government bailout, where after all the properties had been sold, the players would roll the d20, multiply this number by $100, and receive that equivalent in Monopoly money. I also created conditions for the exact opposite: Under recession rules, as voted on by the room when we all just want to go home, upon landing on an opponent’s property the player would roll the d20, multiply this number by 25, and add that to the owed rent.

I also decided to incorporate crime.

During the game with my friends, I imagined real financial burden, the type that leads to homes being foreclosed and children kept from attending college. What would a man do, in order to protect his family in a time of crisis? In the new Monopoly, after choosing who to rob, players would roll the Monopoly dice, combine this number, and then multiply it by the roll of the d20. If the number was equal to or higher than 120, they would receive half of their opponent’s cash. If it was lower, they would go right to jail. I also incorporated a separate penalty: $10 of real money paid to the attempted robbing victim, as restitution for emotional turmoil.

With this rough set of adjustments envisioned, it was time to beta test the rules. On a recent night, I was joined by Outline staff writers Gaby Del Valle and Paris Martineau, audio director James Green, intern Caroline Haskins, senior developer Erik Hinton, and director of partnerships Ally Cuervo, all of whom reviewed the rules ahead of time, and agreed to approach the night in a certain collaborative spirit. We decided to vote on modifications during the game, along with any other rules that seemed to make sense.

We agreed that the sense of optimism over the untrammeled terrain placed the game at the start of the Obama presidency.

At the beginning of the game, James proposed a new concept: determining the order of play by the privilege of the players. The most systemically advantaged of us would get first shot at claiming the property, as in life. We voted yes, and quickly sussed out the order. Erik, a straight white man, would go first; James, a bisexual black man, would go last. I went second, as a biracial — half-white, half-model minority — straight man. Ally, a white woman who attended private school went third; Gaby, a white-passing Latina woman, went second-to-last.

We became attuned to the insinuated symbolism of every move. Erik, on his first turn, collected a Get Out of Jail Free card; I followed by landing on Oriental Avenue; James went to visit someone in jail. We agreed that the sense of optimism over the untrammeled terrain placed the game at the start of the Obama presidency. Quickly, we began to vote on new rules, choosing to allow for deals to be conducted in private, over text or Slack (I voted against this, but acceded to the majority); we lowered the penalty for a failed robbery to $5; we rejected a proposal to incorporate a housing lottery, on grounds it was just too complicated.

The new rules were largely created to impact the more advanced stages of the game, and we began playing without much variation. Properties were divided up somewhat evenly, except for Caroline, who immediately was sent to jail, and failed to roll herself out of the hole. Paris attempted to rob Ally, but rolled a combined three with the standard Monopoly dice, rendering the theft mathematically impossible; Ally then tried to rob me, at first rolling a nine, but the d20 came down as an eight. (9 x 8 = 72, well below the threshold of 120.)

The first successful deployment of the rules came about an hour and a half in, when after procuring St. Charles and States Avenue, I proposed a deal to Gaby for Virginia, in order to attain the first monopoly of the game. Not particularly flush with in-game cash, and not willing to give up another property, I instinctively offered $20 of real life money. A pause came over the room as everybody realized I was serious. She accepted immediately, and everyone was reminded the game was really afoot.

After two hours, we voted to auction off the unowned properties, in order to hurry things up. (Caroline withdrew from the game, as she had other plans; she’d managed to purchase just one property, which she sold to Gaby for $5.) At this point, the first controversy struck. Gaby and Paris, who’d purchased Boardwalk and Park Place respectively, along with other interrelated properties, agreed to merge, combining their cash reserves and cards into a formidable super-team. I protested, citing that mergers were supposed to be for teams that weren’t doing so well, not the modestly rich aspiring to get richer.

A merger is formed in secret.

A merger is formed in secret.

A merger is formed in secret.

The merger was put to a vote, resulting in an argument that was torrid, and unpleasant. We were dead locked — so we sought outside counsel. After hearing both sides, Joshua Topolsky, Outline editor in chief, pointed out that the new rules did specify that the merger was intended for failing businesses. He also invoked the Constitution, noting that in America we abide by the spirit of the original text, even if it seems poorly tailored for modern life. But they’d already moved their properties together, and separating it seemed kind of annoying, so just to get over with, we levied a 20 percent tax on the financial assets of the merging teams, to be evenly distributed to the rest of the players. The compromise left the new Gaby-Paris team with three monopolies, including the desired blue spaces, but cash poor.

Ally and James also chose to merge and pay the 20 percent tax. They now possessed one orange property, while I had the other two — but when Ally offered me $30 of real money, I couldn’t say no. Every team now had at least one monopoly. I soon had hotels on the pink properties, while Erik built on the light blue; the other teams cumulatively owned more spaces, but were much lower on money, meaning their construction efforts went slowly.

It was here that the first flaw of the new rules revealed itself. With a $5 penalty for a failed robbery, and with jail not such a bad place to be with the board filled up and every player one bad roll away from paying hundreds in rent, there was no disincentive for the merged teams to not commit a robbery every turn. If they succeeded, they got half the opponent’s money; if they failed, they paid $2.50 each, and got to sit in prison with their thoughts, while the rest of us nervously attempted to avoid financial peril.

New amendments were proposed. If a player was sent to jail three times for armed robbery, they would get the death penalty, and be out of the game — a crueler punishment provided a more efficient barrier to crime. But moreover, if everybody went to jail at the same time — an increasingly likely scenario — then we would declare the institution of prison morally bankrupt, and abolish it altogether (along with the robberies). This would be the true ideal capitalist world, in which we were all unfettered and free to pursue our financial goals, at no risk of harming our fellow man except by putting them in the poorhouse.

There was one successful robbery all game: after Ally attempted to rob me several times, I robbed her cash-rich merged team. Needing an 18 on the d2o to pull it off, I rolled a 20. The tension of waiting for the second roll, the slim odds landing in my favor, the collective euphoria when it actually happened — this was a rule worth instituting. I immediately used the money to buy back their railroad monopoly. A few turns later, we all rolled ourselves into jail after failed attempts, and tore down the prisons.

A merged team considers its options.

A merged team considers its options.

Here, another flaw revealed itself. The owners of the pink and orange properties were at a statistical advantage, because if you rolled from the jail position, it was nearly impossible to avoid one of them. We’d abolished jail, but we were still rolling from prison — and almost everybody rolled onto one of the orange properties, which now contained multiple houses, sending an incredible amount of money to owners Ally and James.

The game had been going on for more than three hours, and we didn’t seem close to the end. We voted to institute a recession, so that we’d all run through our money. (We’d long stopped paying attention to how many turns we’d taken, rendering the bailout essentially useless — another rule to be tweaked.) I then took out the first loan of the game, borrowing $1000 in case I rolled onto one of the loaded orange properties. Unfortunately, I rolled to carry 180% interest on the loan — and I also landed on orange, depleting my reserves immediately. This was a dark place to be, in debt to the bank with not a lot of time to pay it out. I feigned nonchalance, but everyone at the table sensed the shifting tides. If I didn’t start collecting some money soon, I’d be out of the game.

The goal hadn’t really been to win, anyways. This was an experiment with a different style of play, like tweaking the sliders on a video game to see what fits your comfort level. As I mentally prepared to default on my loan, I felt none of the anxiety attendant to the standard desolation found with the old Monopoly. I’d done everything I could in order to save my business, and thus myself. If I went broke, I could do it with no regrets.

But unbeknownst to me, when I’d been in the bathroom, the merged teams — Gaby and Paris, Ally and James — had stolen money right out of the bank. At several points since, they’d rolled onto hotels beyond their budget — but with the extra cash reserves, they were totally fine. The ruse was revealed by Erik, who’d taken a video of the whole ordeal. And faced with such deception outside the spirit of the game, which had irrevocably changed the course of events so that a fair winner could never be determined, we called the game as a draw.

This was a disappointing anticlimax, yes. We were there for nearly four hours. There were a few lessons here; namely, that you shouldn’t play Monopoly with cheaters. (And ratting out cheaters in Monopoly doesn’t make you a narc; it makes you a hero.) Also, mergers are for cowards.

Nonetheless, it was an instructive experience. The creativity of the other players in amending the rules — wanton theft aside — revealed a basic truth: Monopoly is flexible enough to change. We could make our own version of capitalism, befitting us and your loved ones. We could graft an entire new scaffolding onto the game, transforming it from existential crisis to a bold adventure. But if it never happened again, at least I got $10 out of it.