Understanding the developmental precursors of juvenile violent sex offending can contribute to the promotion of effective early intervention and prevention programs for high-risk children and youth. However, there is currently a lack of research on the early characteristics of adolescents who commit violent sex offenses. Drawing on the literature regarding the generalist and specialist positions of criminal behavior, the aim of the present study was to compare childhood risk factors for three groups of juvenile offenders: (a) pure sex offenders (PSO; n = 28); (b) violent non-sex offenders (VNSO; n = 172); and (c) versatile violent sex offenders (VVSO; n = 24). Nineteen risk factors comprising four life domains (individual, family, peer, and school) were identified from a file review. Three hierarchical logistic regression analyses examined associations between risk factors and offender groups. The results reflected the underlying heterogeneity of the sample, offering support for both the specialist and generalist positions of criminal behavior. PSOs differed from VNSOs on the basis of higher odds for precocious sexual behavior. Second, VVSOs differed from VNSOs on the basis of higher odds for precocious sexual behavior, criminal family members, and an adolescent mother, as well as lower odds for poor school behavior. Third, PSOs were marginally more likely to have engaged in early overt antisocial behavior compared with VVSOs. Fourth, many of the childhood risk factors examined were not associated with any offender group. In conclusion, VVSOs appeared to differ on the greatest number of risk factors from VNSOs, suggesting that VVSOs share a more similar developmental pathway with PSOs. The prevention and future research implications of these findings are discussed. (Contains 5 tables.)