Why Am I Always Going to Jail When Playing Monopoly?
Sometime during the pandemic, I read The Indisputable Existence of Santa Claus by Hannah Fry and Thomas Oléron Evans. It is a delightfully quirky book that blends festive charm with math. And recently, while flipping through some old notes, I was reminded that it includes an entire chapter on Monopoly and how to win it.
Here are some takeaways.
Not All Squares Are Created Equal
One of the book’s biggest insights is that some properties are far more likely to be landed on than others, thanks to how the game works over time. Fry and Evans apply a mathematical model called a Markov chain to analyze long-term probabilities.
Jail is the most visited square on the board. You can land there through dice rolls, Community Chest or Chance cards, or by rolling three doubles in a row.
Properties that show up just after Jail, especially the orange set (Bow Street, Marlborough Street, Vine Street), are prime real estate, thanks to their position relative to where players exit Jail.
At the other end, Park Lane is the least visited property in the game, with just 2.1% of player time spent there.
It’s About ROI
High-rent properties like Mayfair and Park Lane might seem like winning investments, but because they’re so rarely landed on, their actual return on investment is underwhelming. The book compares each property by its rent potential, cost to develop, and number of rolls it takes to break even.
Vine Street (orange) is one of the best-performing properties in the early and mid-game, generating consistent rent and offering quick returns.
The light blue set, also performs well early due to low cost and decent traffic.
Mayfair only becomes profitable after many turns and is weighed down by the poor performance of Park Lane. Despite the big rent numbers, it's usually not worth it.
Sets Matter More Than Individual Squares
Since you can only build on full property sets, understanding which groupings offer the best return based on game length and number of players is essential.
With 1 opponent, aim for orange or light blue. They pay off quickly and dominate in short games.
With 2–3 opponents, prioritize orange and red sets for long-term gain.
With 4 or more opponents, the green properties become worth considering due to the longer game length justifying their higher cost.
There’s also some strategy in how you build houses and when to know it’s time to stop. But let’s be honest, with all the random house rules, cartels, shared investments, and sneaky deals between friends, a lot of the math kind of goes out the window anyway.
But still, if you are playing Monopoly, maybe avoiding Mayfair is not all that bad. And if you find yourself in jail, you are not unlucky. Unfortunately, it is just math.
If you don’t mind geeking out a little, definitely give the book a look. I promise it won’t disappoint.
Cover image taken from Unsplash