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Monopoly and Meaning

Updated: Jul 12, 2025


This is an excerpt from John Ortberg’s book “It all goes back in the box,” with emphasis from me. 


"There is an analogy that comes from the world of games. It was used quite some time ago by a psychologist named James Dobson. I first learned it from my grandmother. My grandmother taught me how to play the game monopoly. Now, my grandmother was a wonderful person. She raised six children. She was a widow by the time I knew her well.


She lived in our house for many, many years. And she was a lovely woman, but she was the most ruthless Monopoly player I have ever known in my life. Imagine what would have happened if Donald Trump had married Leona Helmsley and they would have had a child. Then, you have some picture of what my grandmother was like when she played Monopoly. 


She understood that the name of the game is to acquire. 


When we would play when I was a little kid and I got my money from the bank, I would always want to save it, hang on to it, because it was just so much fun to have money. She spent on everything she landed on. And then, when she bought it, she would mortgage it as much as she could and buy everything else she landed on. She would accumulate everything she could. And eventually, she became the master of the board. 


And every time I landed, I would have to pay her money. And eventually, every time she would take my last dollar, I would quit in utter defeat. And then she would always say the same thing to me. She’d look at me and she’d say, “One day, you’ll learn to play the game.” I hated it when she said that to me. But one summer, I played Monopoly with a neighbor kid–a friend of mine–almost every day, all day long. We’d play Monopoly for hours. 


And that summer, I learned to play the game. I came to understand the only way to win is to make a total commitment to acquisition. I came to understand that money and possessions, that’s the way that you keep score. And by the end of that summer, I was more ruthless than my grandmother. I was ready to bend the rules, if I had to, to win that game. And I sat down with her to play that fall. 


Slowly, cunningly, I exposed my grandmother’s vulnerability. Relentlessly, inexorably, I drove her off the board. The game does strange things to you. I can still remember. It happened at Marvin Gardens. I looked at my grandmother. She taught me how to play the game. She was an old lady by now. She was a widow. She had raised my mom. She loved my mom. She loved me. I took everything she had. I destroyed her financially and psychologically. I watched her give her last dollar and quit in utter defeat. It was the greatest moment of my life.


And then she had one more thing to teach me. 


Then she said, “Now it all goes back in the box–all those houses and hotels, all the railroads and utility companies, all that property and all that wonderful money–now it all goes back in the box.” 


I didn’t want it to go back in the box. I wanted to leave the board out, bronze it maybe, as a memorial to my ability to play the game.

 

“No,” she said, “None of it was really yours. You got all heated up about it for a while, but it was around a long time before you sat down at the board, and it will be here after you’re gone. Players come and players go. But it all goes back in the box.”


And the game always ends. 


For every player, the game ends.

 

Every day you pick up a newspaper, and you can turn to a page that describes people for whom this week the game ended. 


Skilled businessmen, an aging grandmother who was in a convalescent home with a brain tumor, teenage kids who think they have the whole world in front of them, and somebody drives through a stop sign. 


It all goes back in the box–houses and cars, titles and clothes, filled barns, bulging portfolios, even your body."


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In the end we are not the things we owned, but the legacy we leave behind. 


Through our actions and the impact we have on the lives of others. 


And in the end, it all goes back in the box.


New Podcast: Shannon Spotswood of RFG Advisory on RIA Stories (Link)




RIA Stories from Resilient Advisor
RIA Stories from Resilient Advisor


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