My grandmother ... 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 ... 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.