He played in Major League Baseball (MLB) from 1935 to 1943 for the Washington Senators, Philadelphia Athletics, and Boston Red Sox.

[1] Miles began his professional career with the Chambersburg Young Yanks of the Blue Ridge League in 1930.

He was not in the major leagues in 1937 or 1938, but was in the Senators' organization when he was traded to the Philadelphia Athletics for US$30,000 and outfielder Bill Nicholson.

Miles remained with the Athletics from 1939 through 1942 and had his most productive seasons with them, hitting both of his career home runs as a member of that team.

He was acquired by the Boston Red Sox for the 1943 season and played in 45 games with them before being traded in July to San Francisco of the Pacific Coast League for Catfish Metkovich.