Under what conditions are justices able to make decisions that are contrary to the executive's preferences in strong Latin American presidentialisms? To answer this question, I formulate a theory of interbranch relations, particularly of the interplay between courts and justices, on the one hand, and executives and legislatures on the other. The model of strategic prudence involves a game between two players -a court and a government-as well as a stage in which this game takes place, including the institutional design and the political environment. It specifies how players' policy preferences and their assessments of the personal and institutional risks involved in their decision making interact with the institutional setting and the political context. Based on the empirical implications derived from the game, I hypothesize that when courts are institutionally insulated, justices are more likely to decide based on their own preferences, while an institutionally weak court makes them act strategically based on their perception of how the political environment enhances or hinders the government's ability to build a coalition to sanction the court. I test the empirical predictions of the game with the case of the Colombian Constitutional Court (CCC). I combine qualitative evidence, including press coverage and interviews with former justices and law clerks, with a systematic quantitative analysis of an original dataset of abstract review cases decided by the CCC between 1992 and 2006. Given its well-deserved reputation of autonomy and progressive activism, the CCC provides a "crucial case" test of the strategic prudence theory. The analysis of individual judicial decisions provides strong evidence supporting the hypotheses derived from the game's comparative statics analysis. Justices tend to be prudent when they face a strong administration and when the case under review is salient for the executive. In addition, they are more likely to annul legislation when they have stronger preferences against it and when they anticipate that the incumbent would have to pay a higher cost should it attempt sanctioning the court. This dissertation contributes to the subfield of judicial politics in Latin America and is the first comprehensive study of the Constitutional Court in Colombia