Leadership skill is valued by both employers and academic institutions. Research suggests that such skill may be fostered or signaled through leadership experience while in high school, yet few economists have examined the role of such experience in determining future labor market outcomes. Moreover, in the limited research that exists, the studies have been limited to certain sub-populations and have focused on ordinary least squares specifications and results. In this dissertation, I fill these gaps in the literature using two datasets from the National Center for Education Statistics to assess the impact of high school leadership on subsequent educational attainment and post-schooling earnings. I address the non-random selection of students into leadership positions using three econometric approaches: ordinary least squares, propensity score matching and instrumental variables. In chapter II, using each of these methods and data from the National Education Longitudinal Study of 1988 (NELS), I find that high school leadership has a large, positive impact on post-secondary educational attainment. In chapter III, I replicate the analysis of chapter II using data from the sophomore cohort of the High School and Beyond (HS&B). The chapter III results are remarkably similar to the results reported in chapter II of this dissertation, suggesting that the results reported in chapter II are not simply an artifact of the NELS dataset. Finally, in chapter IV, I revisit Kuhn and Weinberger (2005) to provide further evidence on the impact of high school leadership on post-schooling earnings. Using data from both the HS&B and NELS, I first replicate and extend their regression analyses. Then, I estimate the impact of high school leadership on earnings using the three empirical approaches used in chapters II and III. With one puzzling exception, every estimation method, dataset, and model specification examined indicates that high school leadership has a large, positive impact on post-schooling earnings. Taken as a whole, the research coming out of this dissertation corroborates the limited evidence put forth by other economists and implies that high school leadership is, in fact, an important determinant of both future educational and labor market success.