Using rich Texas administrative data, we estimate the impact of middle school principals on post-secondary schooling, employment, and criminal justice outcomes. The results highlight the importance of school leadership, though striking differences emerge in the relative importance of different skill dimensions to different outcomes. The estimates reveal large and highly significant effects of principal value-added to cognitive skills on the productive activities of schooling and work but much weaker effects of value-added to noncognitive skills on these outcomes. In contrast, there is little or no evidence that middle school principals affect the probability a male is arrested and has a guilty disposition by raising cognitive skills but strong evidence that they affect these outcomes through their impacts on noncognitive skills, especially those related to the probability of an out-of-school suspension. Heterogeneity analysis reveals that the principal effect on the probability a male is arrested is strongest for males with the highest predicted risk of arrest based on information prior to middle school entry, while principal effects on the probability of attending and persisting in college span the predicted risk distributions outside of the top decile. Finally, the principal effects on the probability of engagement in the criminal justice system are much larger for Black than for non-black males.