Christopher Ketcham's "antimonpolist history of Monopoly" at Harper's is a great read, a mixture of economic and social theory with a board game everyone knows. There's a section that describes how the original version of Monopoly, called The Landlord's Game was designed to teach people the threats of private property and that the real way to win that version of the game was cooperation. That, of course, is not how most people play Monopoly and in fact, Kethcam's interview with a former Monopoly player reveals how you should be playing the game:
“Monopoly players around the kitchen table”—which is to say, most people—“think the game is all about accumulation,” he said. “You know, making a lot of money. But the real object is to bankrupt your opponents as quickly as possible. To have just enough so that everybody else has nothing.”
Human nature is an ugly thing, eh?