Dropouts have high crime rates, but is there a direct causal link? This study, utilizing administrative data for six cohorts of public school children in North Carolina, demonstrates that those born just after the cut date for enrolling in public kindergarten are more likely to drop out of high school before graduation and to commit a felony offense by age 19. We present suggestive evidence that dropout mediates criminal involvement. Paradoxically, these late-entry students outperform their grade peers academically while still in school, which helps account for the fact that they are less likely to become juvenile delinquents. (JEL H75, I21, J13, J24, K42)