Richard Whitesides was born on January 14, 1937, in Manila, Philippine Islands. He entered the U.S. Military Academy at West Point on July 5, 1955, and was commissioned a 2d Lt in the U.S. Air Force on June 3, 1959. Lt Whitesides next completed Pilot Training and was awarded his pilot wings at Webb AFB, Texas, in October 1960, followed by Helicopter Pilot Training at Stead AFB, Nevada, from November 1960 to April 1961. His first assignment was as an SH-19B Chickasaw Base Rescue Helicopter Pilot with the 78th Operations Squadron at Hamilton AFB, California, from May to September 1961, and then as an SH-19B pilot with Detachment 11 of the Western Air Rescue Center at Hamilton AFB from October 1961 to May 1962. Lt Whitesides then served as an SH-19B pilot with the 41st Air Rescue Squadron at Hamilton AFB from May 1962 to July 1963, followed by service as an L-19 Bird Dog pilot and as a flight training instructor pilot with the 19th Tactical Air Support Squadron at Bien Hoa AB, South Vietnam, from July 1963 until he was killed in action on March 26, 1964. Capt Whitesides was officially listed as Missing in Action until being declared dead on March 27, 1965. His remains were recovered in 2014, and he was buried at the United States Military Academy Post Cemetery in West Point, New York, on May 1, 2015.

His Air Force Cross Citation reads:

Captain Richard L. Whitesides distinguished himself by extraordinary heroism in connection with military operations against an opposing armed force as an Advisor-Pilot of an L-19 aircraft on 24 November 1963. On that date, while piloting his unprotected aircraft, Captain Whitesides directed strikes time after time against heavily fortified Viet Cong positions. Despite their clever attempts at camouflage, he was able to pinpoint numerous Viet Cong positions and marked them for destruction. Even after his aircraft was partially disabled, Captain Whitesides remained in the area, and clearly pointed out the Viet Cong large gun emplacements, which led to their destruction by cover aircraft. Through his extraordinary heroism, superb airmanship, and aggressiveness, Captain Whitesides reflected the highest credit upon himself and the United States Air Force.