Utilizing data from two large samples, cognitive variables were evaluated as potential mediators of the past crime–future crime relationship. In the first study, the reconstructed General Criminal Thinking (GCT_rc) score of the Psychological Inventory of Criminal Thinking Styles (PICTS) was found to mediate the relationship between past adult convictions/juvenile adjudications and future recidivism in 1,101 male federal prisoners. In the second study, a cognitive appraisal of one’s future chances of arrest was found to mediate the relationship between self-reported delinquency between the ages of 13 and 15 and self-reported delinquency between the ages of 17 and 19 in 1,414 male and female members of the 1997 National Longitudinal Survey of Youth (NLSY) cohort. Sensitivity analysis revealed that the mediating effects in both studies were reasonably robust to violations of the sequential ignorability assumption. These findings suggest that cognitive factors may play a role in encouraging continuity from the early to the later stages of criminal involvement.