This study aimed to examine the presence and impact of dynamic protective factors for delinquency in male adolescents with a history of sexual and/or violent offending. Bipolar factors (factors with risk and protective factors being the ends of the same continuum) were examined in male adolescents with a history of sexual offenses against younger children (CSOs; n = 341), a history of sexual offenses against peers and/or adult victims (PSOs; n = 207), and a history of nonsexual violent offenses (VOs; n = 1,356). We conducted secondary analyses on data collected with the Washington State Juvenile Court Assessment and on general recidivism data. ANOVA, correlations, Fisher’s z tests, and logistic regression analyses were applied. Results showed that, in VOs, the number of risk factors was greater than the number of protective factors, whereas in PSOs, and especially CSOs, the number of protective factors was greater than the number of risk factors. Protective factors appeared to be especially important for juveniles with a history of sexual offenses for two reasons. First, the impact of most protective factors on recidivism was larger among juveniles with a history of sexual offenses than among those with a history of violent offenses. Second, protective factors added to the predictive accuracy over and above risk factors in juveniles with a history of sexual offenses, but not in those with a history of violent offenses.