Born in 1920, in Cleveland, Ohio, Harry Squire grew up with a keen interest in the biplanes of World War I and also with the National Air Races that came to his home town once a year. Harry enlisted in the U.S. Army Air Corps in 1942 and was subsequently trained as an aviation mechanic, with a specialization in Turbosuperchargers, used in heavy bombers. In August of 1943, Harry's unit, the 84th Depot Repair Squadron, was deployed to the North Africa theatre and was attached to the 12th Air Force, basing themselves in Telergma, Algeria. After 3 and a half months, the 84th was reattached to the 15th Air Force and moved station to the Italian theatre at the Foggia (Italy) Airfield Complex, where they would be stationed for the duration of the war. There they serviced B-24 Liberator, and B-17 Flying Fortress heavy bombers.

After the War, Harry was lucky because his hometown of Cleveland, Ohio had one of the few aviation mechanic schools in the Nation. Upon completion of his classes there, Harry worked for Executive Airlines, a small regional carrier based in Cleveland, that also used Stearman biplanes to tow advertising banners. It was at Executive Airlines where Harry would meet his future wife, Ruth Turner. Harry and Ruth would go on to spend 61 happy years together and raise 3 children. In 1951, Harry was hired by United Airlines, in Cleveland, and worked as a Mechanic and Inspector until his retirement in 1985. Harry finished his life in his hometown and was laid to rest in 2009 at the age of 89. Many of Harry's photographs of the aircraft participants of the National Air Races are in the possession of the International Society of Air Race Historians.