Senior military leaders wield immense power and influence around the world. Armies march and bombs fly on the orders of people placed in extraordinary circumstances and positions of authority. Given their influence on society, many would reasonably expect that these individuals maintain not only high levels of military expertise, but also high levels of general education. Yet despite this seemingly reasonable assumption, most military leaders simply do not attend civilian educational programs with the same frequency as other professions. Unlike physicians, lawyers, and the clergy, military leaders do not depend on civilian education for their professional development or prospects for success. Despite the assumed benefits of higher education, does graduate education support or subvert the career prospects of military leaders? I argue that civilian education limits the career prospects of military leaders. These leaders do not succeed because of their advanced degrees; they succeed in spite of them. By earning a civilian degree, a military leader assumes a more subtle though still hierarchical rank in the academy. This "hidden rank" competes with the traditionally explicit military hierarchy and burdens an otherwise capable leader. Rather than improve an individual's career prospects, civilian education (1) imposes severe opportunity costs; (2) limits expansion of professional networks; (3) increases professional career uncertainty; and (4) encourages dissent in a world the privileges conformity. My argument stands in stark contrast to conventional wisdom that assumes more education universally leads to positive outcomes. Moreover, the argument challenges those who contend that the system of professional military education or parochial study programs and personal development point the way to success.In this dissertation, I test my central argument against an original collection of personal experiences and observable career outcomes of an elite cohort of American Officers. The Four Star Dataset gathers pertinent biographic and career data that remains publicly available and widely accessible for the 755 individuals that earned the rank of Four Star Admiral or General during their service in the Army, Marine Corps, Navy, Air Force, Coast Guard, or Space Force of the United States. Using a mixed-method approach, I conduct cross-case analyses of all officers to test hypotheses related to both my central claim and to evaluate competing arguments. Next, I unpack the impact of the four causal mechanisms under review by using a structured comparison of two exceptional military officers. I find compelling evidence that suggests civilian education remains a career burden for military leaders. These findings contradict the rival possibility that education improves a military career. They also contribute to a growing body of work that updates our understanding of leaders and the traits that lead to success.