This dissertation explores two critical institutions within the U.S. criminal justice system: plea bargaining and police unions. These institutions wield significant influence over legal outcomes, shaping both individual lives and broader policy responses. By examining these structures through formal models and case studies, the dissertation seeks to reveal how they perpetuate racial inequalities and power imbalances, impacting marginalized communities. Together, these three papers offer a nuanced view of the criminal justice system’s institutional structures, focusing on how plea bargaining and police unions contribute to racialized outcomes and the resistance to reform. This work contributes to discussions on dismantling these structures to address systemic inequalities within the criminal justice system.