The purpose of this study is to examine the adolescents who cross the boundaries of legality, also including illegal political means in their political action repertoire. The data comprised of questionnaire responses from middle and late adolescents in a Swedish city of around 130,000 citizens. Analyses of covariance, EXACON, and logistic regression were used to examine the extent to which adolescents including illegal political activities in their political activity repertoire compare with their legally oriented counterparts. Adolescents using illegal political activity reported higher levels of political interest and goal-orientation than adolescents involved solely in legal political activity. The major contrasts with legal political activism were that illegal political activism seemed to co-occur with (a) reluctance to accept authority, irrespective of the context (societal, school, or parental) and (b) approval of violent political means. In a simultaneous model, further analysis revealed that reluctance to accept authority reduced the predictive power of illegal political activities with regard to approval of political violence. This suggests that the tendencies to approve of political violence, among adolescents involved in illegal political activities, might be partially explained by challenges toward authority. To conclude, adolescents in illegal political activism seem to have similar resources for political engagement as their legally oriented counterparts. However, adolescents involved in illegal political activity seem more likely to let ends justify the means. Most likely, this position is related to authority challenges.