The purpose of this study was to evaluate the impact of different operationalizations of offending behavior on the number and shapes of distinctive trajectories of offending and their associations with childhood risk factors. Prior research with 203 young men from the Oregon Youth Study identified six offender pathways, based on self-report data (Wiesner & Capaldi, 2003). The present study used official records data (number of arrests) for the same sample. Semiparametric group-based modeling indicated three distinctive arrest trajectories from late childhood through early adult years: high-level chronics, low-level chronics, and rare offenders. Both chronic arrest trajectory groups were characterized by heightened rates of early onset and more severe offending. Overlap among self-report and official records trajectory groups was substantial, albeit imperfect. Membership in chronic arrest trajectories was significantly predicted by parental antisocial behavior, child antisocial behavior, child attention problems, and child academic achievement, with the evidence being stronger for common rather than trajectory-specific predictors. Overall, this study demonstrated limited convergence of trajectory findings across official records versus self-report measures of offending behavior.