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Research has documented that compliance with the law is undermined when individuals experience procedurally unjust treatment and perceive authorities and institutions to lack legitimacy. The present study builds off this line of research by exploring the interplay between legitimacy perceptions of the criminal justice system and perceived opportunities for educational and occupational success across racial/ethnic groups. Using multiple waves of data from the Pathways to Desistance study, the present research employs multiple-group structural equation models to analyze the extent to which perceptions of legitimacy of the criminal justice system, conventional opportunities for scholastic and occupational success, and compliance with the law impact one another over time, and whether stability effects, contemporaneous associations, and cross-lagged effects are similar or dissimilar across racial/ethnic groups. The discussion of the research findings is centered on theoretical implications for theories of institutional legitimacy and practical implications for the development of general and group-specific policies to encourage compliance with the law and improve individual outcomes.