In 1928, Hamilton left high school to play professional baseball with the Kinston Eagles in North Carolina. He returned to complete high school, and went on to earn a business degree from the University of Kentucky in 1933. In 1935, Hamilton joined the House of David, a professional level basketball team, where he played and served as the general manager until 1952. In 1938, he returned to baseball on the administrative side for the Cordele, Georgia Bees, in the Georgia-Florida League. He served in administrative roles in Cordele, Pensacola, Florida, Kingston, North Carolina, and Jacksonville, Florida from 1938-1940.

By 1946, Hamilton was named the General Manager of the Binghamton New York Triplets of the Eastern League. By 1949, Hamilton requested a move south; this was granted and he became a scout for the New York Yankees. In 1951, he started scouting for the Brooklyn/Los Angeles Dodgers. In 1969, he followed Buzzie Bavasi from the Dodgers to the San Diego Padres, staying until 1973 when he signed as a scout for the Cleveland Indians. He stayed with the Indians until he retired in 1986.