Not much is known of the early life and career of Harry Fleming, but he proved himself one of the top trainers and drivers during his years (circa 1918) with the Hillanddale Farm, Mamaroneck, New York, where he trained for W. B. Dickerman. He took charge of Nedda when she was two and in 1922 at Lexington, Kentucky, drove her to a 1:58 1/4 trotting record for mares. Fleming won many stakes with her and also was successful with the pacer Russell Boy 2:00 1/4. He remained with the farm until after Dickerman's death in 1923, staying on for a while and managing it for Mrs. Dickerman, who owned Nedda.
Published in the Harness Racing Museum's 1994 book, The Immortals