A Monopoly Champion’s Winning Secrets

“It is in games that many men discover their paradise.” -Robert Lynd

Fifteen years ago I competed for the title of National Monopoly Champion. After I won Utah’s state Monopoly championship, Parker Brothers awarded me an all-expense paid trip to Las Vegas to compete in the national tournament, where I finished fifth overall.

I missed out on the final game by just one position. I’ll go to my grave feeling confident that I would have won that championship game.

Being the first player excluded from a seat at the championship table was hard. Watching the eventual champion use the same strategy I had used to beat him in the first round made it even harder.

I’ve learned a lot about life by playing Monopoly. During my teenage years I had stretches where I spent more hours playing Monopoly than I did sleeping. I’d play anyone who’d accept my challenge. When no one would, I’d compete against myself, playing all four (or sometimes eight) positions myself.

In Monopoly, every other game, and life in general, I hate losing even more than I love winning. And I can’t think of anything that I love more than winning.

I can’t stand the smacking, stinging quality that losing possesses. If there’s any upside whatsoever, it’s that losing can provide perfect clarity, deeply impress lessons, and impart an intense determination to perform better in the future.

Playing a game of Monopoly with me doesn’t resemble the games that most people played as children. It generally takes me only 45 minutes to finish a four-player game.  

Some people think that Monopoly is merely a game of luck, or a simple kid’s game. I like to invite those people to play a game with me.

Of course, any game that uses dice contains an element of luck. But there’s a lot more to winning Monopoly than rolling well. It helps to know the rules inside and out, and to use them fully to your advantage.

Many years ago I bought and studied a book called The Monopoly Companion. It provides statistical tables showing which color groups provide the best return on investment, which properties are landed on most often, and a host of other insights and tips that increase a player’s chances of winning when applied consistently.

Monopoly’s rules are a bit like tax laws— most of them aren’t all that complex, many of them are situational, and by the time they’re all layered on top of one another they can seem pretty overwhelming. Those who understand them well and bend them to their favor benefit far beyond those who don’t.

I quit being surprised a long time ago that most people don’t know or play by Monopoly’s rules. It’s one of my life’s minor joys to witness an opponent’s surprise when I invoke one of the more obscure rules at a pivotal point to tip a game irreversibly in my favor.  

One of my favorite rules to exploit is the housing shortage. It’s based on the fact that there are only 32 houses in the game, and once they’ve all been purchased no one can buy a hotel even if they have the money to do so. It’s the kind of thing that doesn’t seem like a big deal, but used correctly it can be game-defining.  

Another strategy I employ is memorizing the sequence of the Chance and Community Chest cards. There are sixteen of each, and because they stay in the same order, if you pay attention once you’ve seen them all you’ll know which ones are coming up.

This allows me to make more intelligent trades, to build (or abstain from building) houses or hotels at the most strategic times, or to hold cash in reserve when I’m at high risk of landing on a card that would require a large cash outlay.

Also, I don’t put money in the “Free Parking” square. First, it’s not in the rules, and second, it makes absolutely no sense to infuse cash into the monetary system of a game whose point is to bankrupt your opponents.

One thing I absolutely believe increases my odds of winning is that I exert positive belief into my play. Every time I roll the dice, from the moment I pick them up, I look at what I want to roll and repeat that number in my mind, or often out loud. It’s amazing how often I roll what I want.

By contrast, I have a friend who loudly announces what he doesn’t want to roll— the Go to Jail square, the property that’s already been purchased, or the one with a hotel on it that will bankrupt him if he hits it. I swear that he lands exactly what he doesn’t want to more often than he avoids it. 

It reminds me of Henry Ford’s saying, “Obstacles are those frightful things you see when you take your eyes off your goal.” It also makes me think of what race car drivers are taught about “target fixation,” or looking where you want to go rather than where you don’t want to go.

One of the things I love about Monopoly is that unlike life, it is a closed system with clear rules and knowable and (mostly) predictable outcomes. I also love that every loss can be easily wiped from memory with a subsequent victory.

From Monopoly I’ve learned that before you even sit down to play you’ve got to have absolute confidence that you’re going to win. I’ve learned that it’s important to take action— to ask for what you want and to be creative when dealmaking. I’ve learned that it’s important to pay attention— after all, opponents don’t owe you rent if they land on your property and you don’t ask for it.

Monopoly has taught me that it’s possible to overcome seemingly impossible adversity— I’ve won games where I was only able to purchase a single property the entire game. Of course, it helps to know the rules backwards and forwards and to use them to your advantage whenever possible. 

But as much or more as any of these lessons, I’ve learned that there’s immense power in focusing on and believing in the best possible outcome. I’m amazed at how often it becomes reality. 

I don’t know why it works, but I know that it does.

In my mind I’m undefeated still.

I invite you to share with me your favorite memories or aspects of Monopoly!