Master Sergeant Winegardner was an aerial photographer on an all weather bomber, RB-36H, with the 718th Squadron, 28th Strategic Reconnaissance Wing based at Rapid City Air Force Base, South Dakota. On 18 March 1953, his aircraft was flying low on a simulated combat mission from Lajes, Azores, to Rapid City when it struck a 896 foot hill, killing all 23 on board.

Winegardner was awarded the National Defense Service Medal.