As gambling activities became more accessible, an increasing amount of research established a link between pathological gambling and crime. The observation that a gambler’s lifestyle carries him toward involvement in crime became so common that the idea of a gambling-crime cycle became a fixture in past research. This seemingly evident ‘fact’ is, however, not given. This article illustrates how individuals are confronted with a series of factors that may modify their gambling careers and their involvement in crime. Based on twenty interviews, the personal trajectories of gamblers are examined in view of various features, which may make them susceptible to criminal involvement. Gambling trajectories are analyzed as careers and particular focus is aimed at revealing the onset, evolution, and, at times, desistance phases for gambling and crime involvement. Factors influencing the overlap between gambling and crime involvement include the presence of family and close friends as both agents of deterrence and suppliers of criminal opportunities, the expected effects of financial and family stress, fear, or, on the contrary, the pre-dispositional behavior of gamblers and, finally, the competency of gamblers who are able to finance and extend their gambling activities over prolonged periods. These observations permit a re-assessment of the gambling-crime cycle by introducing the basic features of a variety of pathological gambling careers that could neutralize, delay, or accelerate the passage to criminal involvement.