Robert Scott Whitman, Jr. was born on 1 January 1916 at Johnson City, New York. He was appointed a midshipman on 24 August 1935 and graduated from the United States Naval Academy with the Class of 1939. After sea duty on the heavy cruiser from 26 June 1939 to 1 February 1941, he then underwent heavier-than-air instruction at the Naval Air Station Pensacola, Florida. He earned his wings there and then received further instruction at the Transition Training Squadron, Pacific Fleet, before he reported to Patrol Squadron 44 (VP-44) on 4 November 1941.