Railroads. Utilities. The treasured Oranges. The infamous Browns. Each of three players hunted property like an apex predator in its natural habitat, throwing money to the bank without regard for price or value.

On the first day of Thanksgiving Break, I sat around my living room table with two fellow Grotonians. Kim suffered the wrath of the die, with words such as “Just Visiting,” “Chance,” “Free Parking,” and worst of all, “Income Tax.” On the other hand, John and I were blessed with the Vermont Avenues and Marvin Gardens, the Pennsylvania Railroads and Community Chests. As a rainbow of cards gathered in front of me, Kim’s side of the table remained empty. But who doesn’t love an underdog story?

With no monopolies on the board, only two unsettled properties remained: the Reds and, unfortunately, the Browns. With two Blues, I eyed the Connecticut Avenue laying in John’s hand. And so from the farthest reaches of my heart, I pulled the most generous deal imaginable: $600 and two Purples for just one property. Surely, no businessman could decline such an offer. But John was the worst type of player, refusing to make deals until he was certain of his own victory. And so the game dragged on. 

Miraculously, two things happened at the same time. I landed on both Browns, gaining the first and arguably worst monopoly. And Kim, in a stroke of luck, gained the unsettled Yellow monopoly. As we began developing houses, it seemed that Kim’s victory was inevitable—just one misroll could cost John and me upwards of $700. While a pass through my Brown monopoly could be paid off with merely the Go money—or so it seemed. Again and again, Baltic Avenue struck gold, draining Kim and John of their hard-earned cash. Meanwhile, Kim’s flash of good luck disappeared, as we narrowly avoided his Reds with the Free Parking and Chance. I accumulated Greens with my avalanche of income, building house after house until John had no option but self incarceration. 

With a hotel on Pennsylvania Avenue, the game ended with a few well timed misrolls. I savored the sight of John searching frantically for some way, any way, to pay back his debt to me. Kim mortgaged properties, sold houses, negotiated deals, but soon enough there was nothing left to give. I was the winner.