The gambler’s probing of luck in games of chance cannot be reduced to rational calculation. The art of gambling flourishes at the margins of societies and undermines the correlation of effort and entitlement. This paper interprets the peculiar thrill of gambling in modern times by drawing on social systems theory and critical theory. It argues that gambling is a specific mode of agency that consists in a playful engagement with risk and contingency. The gambler reveals a highly aroused and yet passive consciousness. Success in gambling depends on the art of proper timing as well as a preconscious awareness of fortune.