The Best Monopoly Strategy, Tested on 300 Million Games

Summary

The video tests eight Monopoly strategies across more than 300 million simulated games, using official rules: unbought properties go to auction, building must be even, and mortgages, Jail, and both card decks work as written. The simulation’s landing-rate results were checked against a 1996 Scientific American table. Because the AI players could not negotiate freely, their only permitted trades were swaps that completed a color set for both players.

Tournament results

Across tables of four, the strategies won:

• All In: 43%
• Buy Everything: 29%
• Three Houses: 23%
• Cheap Side and Expensive Side: 22% each
• Saver: 16%
• Never Trades: 14%
• Railroad Baron: 3%

In separate tests, a standard Buy Everything player won about 21% of games. Roughly one in six games never finished.

Four strategies that hurt

• Being picky: Skipping properties leaves them available for opponents to buy at auction. Properties you pass up can also be useful in trades. A player buying only orange and red won under 3% in the test. Skipping utilities caused little harm, but skipping brown or Boardwalk and Park Place was costly.
• Saving cash: Players who kept a reserve—including one that saved enough to cover the worst rent—won less often than a player that spent its last dollar building. Cash does not earn rent.
• Stopping at three houses: Three houses give an excellent rent increase for their cost, but stopping there is the wrong lesson. The advantage came from reaching three houses quickly. Mortgaging other properties to fund building was the most helpful single habit tested.
• Refusing to trade: Never Trades won just 6.5% in a focused test, and games without trades often failed to end. Even a cautious trader that rejected deals favoring the other player did worse than one that accepted trades.

Which properties and sets to target

When players were given complete color sets to compare, orange performed best, followed by red and pink, with light blue close behind. Green and dark blue ranked near the bottom; only brown did worse.

Orange is inexpensive to build on and sits six, eight, and nine spaces after Jail, a frequently revisited square. With three houses, orange recouped its cost after 29 opponent rolls, compared with 37 for green. Light blue beat Boardwalk and Park Place six times out of ten in these tests.

The tuned strategy and practical advice

A computer-tuned player won 26% against three standard players and 41% against three Savers. Its tested approach was to:

• Buy everything it lands on.
• Build to three houses quickly, then continue toward hotels.
• Mortgage spare properties to build, buy properties, and bid at auctions.
• Bid above a property’s printed price—up to three times the price when it completes a set for itself or another player.
• Accept trades.
• Stay in Jail once houses are on the board.

The overall takeaway is to buy broadly, invest rather than hoard cash, build quickly, and trade to complete sets—especially orange when there is a choice. Against similarly strong players, however, luck still matters considerably. The simulation could not account for human bluffing or persuasion.

Featured players and sources

• Players: Buy Everything, All In, Saver, Three Houses, Cheap Side, Expensive Side, Railroad Baron, and Never Trades.
• Additional test strategies: An orange-and-red-only buyer, a careful trader, and the computer-tuned player.
• Presenter: Leo, briefly appearing as “Leo from the future.”
• Source cited: A 1996 Scientific American table of Monopoly landing frequencies.