This paper analyzes the selection processes behind post-schooling transitions into college enrollment, military service, long-term unemployment, and incarceration relative to civilian employment, examining to what extent these processes are racialized. Rather than analyzing a complete set of alternatives, previous research typically focuses on a limited set of these alternatives at a time, and rarely accounts for incarceration or long-term unemployment. Using individual-level panel data on the first post-high school transition from the National Longitudinal Survey of Youth 1997 Cohort, results show that white men experience positive transitions (college enrollment and military service) at higher rates and for longer periods than black men, who experience negative transitions (long-term unemployment and incarceration) at higher rates for longer periods than whites. Competing risk Cox regression analyses reveal that blacks’ transitions are polarized, showing that blacks in the upper distributions of standardized test scores and socioeconomic status are more likely to pursue a college education relative to their white counterparts, whereas blacks in the bottom of the standardized test score and socioeconomic status distribution are more likely to experience negative transitions than whites. Unlike prior research finding that military service provided “bridging careers” for racial minorities, black men are no longer more likely to join the military than whites. Instead, blacks now face a much higher risk of incarceration. Implications for intra-generational mobility and changing opportunity structures for racial minorities are discussed.