We develop a framework for understanding how legal structures relate to imprisonment. We hypothesize that relatively more hierarchy within criminal justice institutions, compared to commercial law, fosters higher rates of incarceration. Our framework predicts that incarceration reflects asymmetric opportunities for rent seeking across differently organized legal institutions. Instead of comparing criminal justice institutions across nations in absolute terms, we investigate the relative degrees of institutional centralization across legal spheres. To provide support, we document the separate historical experiences that shaped divergent organizations across England and France. Within each country, criminal legal institutions developed inverse organizational traits from commercial legal processes. As a result, the contrasting organizations created asymmetric opportunities for rent seeking. Divergent contemporary outcomes can be understood by recognizing these initial organizational choices, the relative opportunities they created, and their subsequent path dependencies. We document contemporary England, France, and the United States’ incarceration trends and penal outcomes to provide empirical support.