For Pynchon’s players, more often than not cheaters and fraudsters, use such games of chance to fulfil their longing for emancipation and flight, at a time in history when the American continent is about to be mapped by the abstractions of colonial companies and Enlightenment science. As opposed to agôn, a category of games that Roger Caillois delineates in Man, Play and Games (1958) as “a combat in which equality of chances is artificially created, in order that the adversaries should confront each other under ideal conditions,” alea encompasses games of chance which are “a strict negation of controlled effort, efficacious resort to skill, power, and calculation, and self-control respect for the rules the desire to test oneself under conditions of equality.” It will be my contention that alea, in Pynchon’s novels, offers the possibility of an alternative world and becomes a necessary mode of resistance in the face of a plenty-flushed adversity which threatens to hold sway over the American continent. This paper seeks to consider games - and more particularly card games and gambling - as an American form of resistance in Thomas Pynchon’s novels.