Monopoly Meltdown

I have always hated the game Monopoly. Not “mild dislike” hate — I mean deep, irrational, full-body dread. The kind that sits in your gut and stays there for decades.

When I was a kid, Monopoly was the family game. My brother Paul and I were lucky — our parents actually played board games with us. Later in life, Scrabble became our go-to, as Paul wrote about in his blog. But when we were young, Monopoly ruled the table. And I hated every roll of it.

Family game night was supposed to be fun, but for me, it was an uphill climb. Everyone else was older. I knew the basic rule — buy early, build quickly, crush your opponents — but something always went wrong. I’d land on the wrong properties, roll low numbers, or worse, have to hand over whatever little I owned. Paul, two and a half years older and armed with the mischievous instincts of an older brother, never missed a chance to make it sting.

And yet, I loved the hat. Always the hat. It had style, a little quiet dignity — maybe that was my protest.

But the game itself? Pure torture. The board filled with houses, then hotels — red and green reminders that I was losing ground fast. My mom would kindly help me mortgage my few sad properties. “Look, honey,” she’d say when taking them out of my hand, “if we do this, you can pay your brother.” Pay my brother. Perfect.

Then came the final blow — Boardwalk and Park Place. Nobody else ever landed on them. Only me. Every single time. I could see it coming before the dice even stopped rolling. I’d count the spaces, know what was next, and still feel the punch when it happened.

At one family game night I started crying when I hit Boardwark. In one glorious, dramatic burst of frustration, I slid my hands under the board and flipped the whole thing into the air — pieces, hotels, money, everything. My parents were not thrilled. I stomped off down the hall, gasping and hyperventilating, to the bedroom and slammed the door behind me.

Standing there and trying to calm down, I suddenly realized I was NOT in my bedroom. Trying to straightened myself up I opened the door and muttered “Wrong room!,” and stomped to my real one. The game went on without me as best they could with piecing it together. I never played Monopoly again.

Years later, when my kids were old enough, I gave it another shot. I tried to tell myself it was just a game. But that familiar unease crept in — that sense that no matter how smart you played, fate could still send you crashing. Some feelings just stay with you.

Our family plays other games now — Scrabble, Ticket to Ride, Catan — and those, I love. They’re about thought and connection, not luck and loss. They bring laughter, conversation, and comfort. Monopoly still makes my stomach tighten, but maybe that’s okay. Maybe we’re all wired to have a few things that still get to us.

I think about that boy — sitting cross-legged, hat token in hand, doing his best to hang in there while the odds stacked up against him. I’ve spent a lifetime trying to make sense of things like that — building, creating, designing systems that bring order to chaos. Maybe that’s my version of rewriting the rules.

Because life, as I’ve learned, isn’t about who owns Boardwalk or who ends up broke. It’s about who’s still at the table with you — your family, your people, your sharks — rolling the dice together, laughing through the bad rounds, and finding joy in the little things.