The links between gambling and criminal offenses have been frequently reported, but the pathways from gambling to a particular offense have not. Our study applied a pathways model to predict participants’ income-generating, drug-related, and violent offenses stemming from their craving for gambling. The participants were 332 male inmates in a Japanese local prison. They answered questionnaires on gambling behavior, alcohol addiction, Internet addiction, impulsivity, and psychopathy. Their official records with information on their current offense, sentence length, number of imprisonments, and length of education were also analyzed. The results show that 38.55% (n = 128) of the participants had a probable gambling disorder, a rate of problem gambling at least four times higher than that among the general Japanese population. Furthermore, their craving for gambling predicted their income-generating offenses, but not their drug-related and violent offenses. Their craving for gambling can thus be linked to their financial issues, rather than their emotional and impulsive issues. The pathways model explained the path not only from addiction/psychopathy to gambling, but also from gambling to committing an income-generating offense.