In this paper I investigate the importance of various types of legitimacy on the career trajectories of individuals in leadership positions. Using data from NCAA basketball coaches as an empirical setting, I propose that pragmatic legitimacy (performance), cognitive legitimacy (recognition) and moral legitimacy (compliance) are significant predictors of career advancement. Results from Cox regression survival analysis indicate that among all variables, affiliation with high status actors, a measure of cognitive legitimacy, is the strongest positive predictor of likelihood of career advancement (even when controlling for performance). Results also indicate that members of minority groups advance at a slower rate regardless of actual performance.