Les Holland was born on July 11, 1927, in Liberal, Kansas. He enlisted in the U.S. Marine Corps in April 1945, and served until his honorable discharge in July 1946 as a Private First Class. Holland entered the U.S. Naval Academy in June 1951, and upon graduation chose to receive his commission as a 2nd Lt in the U.S. Air Force on June 3, 1955. He next attended Primary Pilot Training at Moore AFB, Texas, from June 1955 to March 1956, followed by Basic Pilot Training at Greenville AFB, Mississippi, from March to October 1956. His first assignment was as an F-86 Sabre pilot with the 311th Fighter-Bomber Squadron at Osan AB, South Korea, from October 1956 to October 1957, and then as an F-86 and then F-100 Super Sabre pilot with the 10th Fighter-Bomber Squadron (renamed the 10th Tactical Fighter Squadron in July 1958) at Toul Rosieres AB, France, from November 1957 to December 1959. Capt Holland moved with his squadron to Hahn AB, West Germany, in December 1959, and then returned to the United States and served as an F-100 pilot with the 522nd Tactical Fighter Squadron at Cannon AFB, New Mexico, from October 1961 to January 1962. His next assignment was as an F-100 pilot with the 478th Tactical Fighter Squadron at Cannon AFB from January 1962 to September 1965, and during this time he deployed to Homestead AFB, Florida, during the Cuban Missile Crisis from October to December 1962, and to Takhli Royal Thai AFB, Thailand, from December 1962 to February 1963. Capt Holland served as an exchange pilot with the U.S. Army and flew UH-1 Iroquois helicopters with A Troop, 1st Squadron, 9th Cavalry Regiment of the 1st Cavalry Division in South Vietnam from September 1965 to March 1966, and then served as an F-4 Phantom II Instructor Pilot with the 4454th Combat Crew Training Squadron at Davis-Monthan AFB, Arizona, from March 1966 to July 1967. His next assignment was as an F-111A Aardvark pilot with Detachment 1, 4481st Tactical Fighter Squadron (redesignated Detachment 1, 428th Tactical Fighter Squadron in January 1968) at Nellis AFB, Nevada, from July 1967 to January 1969, and during this time he participated in the Harvest Reaper and Combat Lancer program to deploy the new F-111 for combat in Southeast Asia, flying combat in the F-111 out of Takhli Royal Thai AFB, Thailand, from March to November 1968. Major Holland next served as an Operations Staff Officer and F-111 Weapons System Project Officer at Headquarters Tactical Air Command at Langley AFB, Virginia, from January 1969 to May 1971, followed by service as an F-111 Flight Commander with the 79th Tactical Fighter Squadron at RAF Upper Heyford, England, from June 1971 to December 1972. He then deployed to Takhli Royal Thai AFB, Thailand, and flew combat as an F-111 pilot attached to the 6280th Combat Support Group during December 1972 for Operation Linebacker II. Major Holland remained in Thailand, and joined the 429th Tactical Fighter Squadron there, serving as an F-111 Aircraft Commander from August 1973 until he returned to the United States in November 1973. His final assignment was as an F-111 Aircraft Commander with the 391st Tactical Fighter Squadron at Mountain Home AFB, Idaho, from November 1973 until his retirement from the Air Force on January 1, 1977. Les Holland Flew West on May 13, 1999.

His 1st (of 2) Distinguished Flying Cross Citation reads:

Major Leslie R. Holland Jr., distinguished himself by extraordinary achievement while participating in aerial flight as the aircraft commander of an F-111A over North Vietnam on 16 April 1968. On that date, Major Holland performed a night low level strike against a heavily defended target in adverse weather conditions. In spite of malfunctioning aircraft equipment, Major Holland skillfully piloted his aircraft through rugged terrain and around the defenses to destroy an important target. The professional competence, aerial skill, and devotion to duty displayed by Major Holland reflect great credit upon himself and the United States Air Force.