Problem gambling behaviors, particularly the most severe form, which is pathological gambling (PG), represent an emerging public health problem. Compared with the general population, individuals with problem gambling are more likely to have reports of legal issues, including commission of crimes, arrest, and incarceration. The goal of the present study is to examine the characteristics of individuals seeking help for gambling problems with regard to reports of illegal behavior secondary to gambling. Individuals with gambling problems were identified through use of a 24-hour gambling helpline, and information regarding the identified problem gambler was investigated with respect to reported presence or absence of gambling-related illegal behaviors. Identified gamblers with reported gambling-related illegal behaviors compared with those without such behaviors appeared to experience more severe gambling-related problems. Despite being on average younger, gamblers with acknowledged gambling-related illegal behaviors were more likely to have reports of having problems with multiple forms of gambling, debts to acquaintances, been suicidal secondary to gambling, used alcohol or drugs excessively, and received mental health treatment. Secondary analyses of the subgroup of gamblers with gambling-related illegal behaviors revealed that those with reports of arrest or incarceration secondary to gambling compared with those with gambling-related illegal behaviors but without arrest or incarceration secondary to gambling were more likely to have features similar to those described for individuals with antisocial personality disorder (ASPD). That is, the gambler with reported arrest or incarceration secondary to gambling was more likely to be male, unemployed, single, and have reports of problems with excessive drug or alcohol use. In contrast, the gamblers acknowledging gambling-related illegal behaviors but not arrest or incarceration secondary to gambling were predominantly female and more likely to have reports of problems with non-strategic forms of gambling (e.g., slot machine), owing money to legitimate sources of borrowing, having filed for bankruptcy, and having family problems related to gambling. The findings indicate: (1) individuals with reported legal problems secondary to gambling represent a more ill subpopulation of problem gamblers; and (2) there exist separate subgroups of gamblers with gambling-related illegal behaviors (i.e., those with or without reported arrest or incarceration secondary to gambling) with strikingly different characteristics and possibly different treatment needs. The results of the present study highlight the importance of the identification and treatment of individuals with gambling problems with respect to legal issues.