The development of strategy and the provision of strategic guidance are essential to the long-term success of any organization. This is especially true for massive bureaucratic organizations like the United States Department of Defense (DOD), which need strategy to align the purpose, processes, and resources in a system that spans the globe, covers multiple years into the future, and guards the security interests of the nation. Unfortunately, DOD has engaged in almost two decades of strategic wandering since the conclusion of the Cold War. This research effort focuses on the causes for this astrategic approach by evaluating the absence of grand strategy at the national level, the resulting misalignment and distortion that has occurred in the defense policy, planning, programming, budgeting, and acquisition processes, and the role DOD has played in fostering this strategic shortfall. The critique utilizes the expected fiscal austerity and complex threat environment of the next decade argue that the current unconstrained strategic approach is unsustainable. DOD must desist in its passive approach to strategy and, instead, drive the strategic development process, execute a genuine strategic review, foster a new value culture within the department that focuses on national loyalty and moral courage instead of parochialism and status quo, and advocate for a new roles and missions review for the Services and Defense Agencies.