Squander
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Squander (written as "$QUANDER" on the box and in the rules) was an Avalon Hill board game based loosely on the game Monopoly, but in reverse. As in Monopoly, players rolled dice and moved around a board, encountering opportunities to make financial decisions. The object, however, was to lose money rather than gaining it. Each player started with a million "Squanderbucks," and the winner was the first player to go broke. The game was published in 1965.