The Department of Defense has had a long and illustrious medical history. Whether serving during wartime or peace, for short periods of time, or an entire career, there has been a broad spectrum of development in the academic surgical community. While many academic surgeons with military backgrounds served limited obligations either before or after subspecialty training, they then proceeded to start a “second career” in academic surgery. This chapter will focus on the small group of individuals who were able to start and develop academic surgical careers while on active duty and were then able to translate that into senior academic leadership positions post their military retirement. This will serve as a case study for eight academically successful surgeons, who all spent 20+ years on active duty, and they were prepared by their military experiences and where they eventually landed as civilians.