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He was the Kentucky Wildcats football coach in 1917, compiling a 3-5-1 record. He also served as Kentucky's basketball coach in 1918, compiling a 9-2-1 record. The rare basketball tie, against Kentucky Wesleyan College, was because of a scorer's error that was not discovered until after the game had ended and both teams had departed.
His brother Ewing T. Boles was a noted businessman and philanthropist.