Jim Connolly grew up in a small Indiana town where his dad owned a restaurant and his mom worked in a drugstore. He got his first exposure to West Point when the Army football team stayed in a hotel in his town prior to a game at Notre Dame. He attended Indiana University for a year prior to entering the Academy. Jim did well in math and engineering courses, ran track and cross country for two years, and was a Rabble Rouser his Firstie year (all Rabble Rousers were Firsties in those days). He and his future wife, who was also from the same hometown, started dating during his Firstie year while she attended school in New York City. He commissioned as an Artillery Officer and initially served in an Airborne artillery unit at Fort Bragg and in a mechanized unit in Germany before going to Vietnam. He spent over seven months in the field as an advisor to Vietnamese popular forces before spending the last few months of his tour as a Protocol Officer at MACV HQ, during which time he had the opportunity to escort General of the Army Omar Bradley. He attended graduate school and returned to West Point to teach math in the early ‘70s. While serving at the Academy, he decided to attend medical school. Jim had to clear several bureaucratic hurdles to make it all happen, but with some help from some West Point connections he made it work. He went on to a long medical career in the Army, capped by command of the hospital at Fort Jackson, South Carolina, before retiring from active duty and going into private practice. In this interview Jim talks about the different phases of his long and distinguished career, ranging from Germany to Vietnam and the medical world. He shares several unique insights from his time as a doctor, comparing it to his “previous life” as an Artillery officer, and then concludes with some thoughts about what West Point means to him.