This chapter describes how the Caribbean Court of Justice is embedded within colonial legacies that have affected regional political norms and legal culture. It shows the CCJ’s decisions are characterized by moderate deference, infrequently ruling in favor of states and typically eschewing restrictive interpretation. More deference, however, is observed through the Court’s remedial orders. The chapter links the CCJ’s tendency to not defer to its intermediate political constraints. Specifically, the CCJ’s strategic space is shaped by high formal independence that is partially offset by homogeneous state preferences. These factors combine to affect the Court’s legitimacy and signal when state resistance might be feasible and credible. In particular, the CCJ defers more when states are clearly aligned. The Court’s nondeference is facilitated by the Court’s practices of persuasive argumentation and public legitimation. The chapter also suggests the CCJ’s support network lacks the robustness necessary to account for its moderate deference.