Analysts attempted to understand what was unique about gambling: the unpredictability, the excitement of risk, and the erotization of tension and fear. They emphasized its competitive aspects and described the language of gambling in order to show its sexual and aggressive gratifications. In the psychoanalytic literature on gambling, one finds unconscious guilt postulated as a force behind the pathological gambler’s self-destructiveness but with multiple explanations to account for that guilt. There are some who believe that all self-destructive behavior is masochistic. According to G. G. Forrest: Alcoholism is a form of masochism. An alternative to the term masochism, aimed at getting away from its historical usage and connotations of sexual perversion, is self-defeating personality disorder. Gambling offers an escape from problems and serves to self-medicate intolerable affect. The chapter provides clinical vignettes and a more extended treatment account to re-establish the legitimacy of the masochistic gambler and to demonstrate some distinguishing features.