Monopoly is one of my favorite games. It is just the right mixture of probability, deal making, strategy and numbers. Monopoly is a game of working with luck and other people.
My key philosophy is: Do things that maximize your chance of winning. Most people play to avoid losing. However, nobody cares about 2nd place. With 4 players, everyone starts the game with only a 25% chance of winning. Playing risky increases your chance of winning (which you care about) and your chance of losing early (which you don’t care about). Below are some tactics that I have found maximize a player’s chance of winning. Of course, many also increase the chance of losing quickly, but that doesn’t matter.
Tactic 1: Get as much real estate as possible. The first stage of the game is all about acquiring a monopoly while stopping other people from doing so. If you can’t get a Monopoly, get real estate that can be traded for a Monopoly. Trading helps the two people who made a trade. Trade until you get a Monopoly and don’t encourage others to trade. Early in the game, people overweight cash for real estate. People also feel more comfortable trading a Monopoly to you when you have no cash; another advantage of being real estate rich & (see next tactic) cash poor.
Tactic 2: Mortgage and build aggressively. Rent doesn’t increase your chance of winning so ignore it. You should have a lot of real estate from tactic 1. Once you have a Monopoly, mortgage properties to build on your Monopoly. Build in a concentrated way on one or two Monopolies. Investing until you’re broke in a Monopoly slightly increases your chance of losing, but it dramatically increases your chance of winning. I like to focus on a cheaper monopoly that you can build up quickly.
Tactic 3: Create a cash cow (a cheaper monopoly that is fully developed), and build towards a knock out punch. In the middle of the game your properties should be generating cash for you to reinvest. If you don’t have an “expensive” monopoly, you can should try to get one. Use the cash from your cheaper monopoly to help you acquire an expensive monopoly. With enough investment, these eventually become knock out punches. The cash generators can be low cost properties with hotels or higher cost properties with a few houses. Only mid to high cost properties can be knock out punches. If you have a cash generator, but not a knock out punch, consider giving someone a free pass in exchange for a card that give you a knockout punch monopoly. (similar strategy to scaling a startup)
Tactic 4: People will be terrified of your Monopoly. To avoid losing if you’re poor from your reinvestments, trade free passes with people that have Monopolies. Again, trades help both traders and implicitly hurt both other people. Trade often.
Tactic 5: The red & orange are both the best for their sides of the board. However, it’s more important to get a Monopoly first than it is to get a specific Monopoly.
Tactic 6: 7 is the most likely number to be rolled (~17% chance), followed by 6 and 8 (~13% each). When someone is 7 spots away from something you own and either 6 or 8 away from another, build. There is a 30% chance they hit you and you get an immediate return while building towards a knockout punch.