Generally speaking, risk assessment tools are based on static or historical “predictors” such as criminal history. This study revisits the relationship between the criminal history and violent/sexual recidivism using a longitudinal perspective by taking into account the dynamic aspect of criminal careers. More specifically, the study attempted to answer the following question : Are offending trajectories carrying any predictive value to help informing about the risk of reoffending following prison release ? The study is based on a quasi-population of adult sex offenders incarcerated in the province of Quebec between 1994 and 2000. Latent class analyses were performed to identify the presence of offending trajectories. Survival analyses showed that offending trajectories do inform about the risk of violent/sexual reoffending, but in doing so, highlighted some important limitations of current actuarial prediction methods.