Distinguishing trajectories of criminal offending over the life course, especially the prediction of high-rate offenders, has received considerable attention over the past two decades. Motivated by a recent study by Sampson and Laub (2003), this study uses longitudinal data on conviction histories from the Dutch Criminal Career and Life-Course Study (CCLS) to examine whether adolescent risk factors predict offending trajectories across the life span. The CCLS is particularly well suited to study developmental offending trajectories as it contains detailed information on individual criminal offending careers for a representative sample of all individuals convicted in the Netherlands in 1977 (n = 4,615) beginning at 12 years of age and continuing into late adulthood. To assess predictive ability, the authors employ two different analytical approaches. First, the authors examine whether offending trajectories can be prospectively differentiated by risk factors identified in adolescence. Second, the authors use group-based trajectory analysis to retrospectively identify distinct developmental offending trajectories and employ a crossvalidation technique to examine the ability to predict the probability of an individual’s membership in a particular trajectory group. Overall, the results support the notion that it is difficult to predict long-term patterns of criminal offending using risk factors identified early in the life course.