Crandall's first overseas flying assignment was to Wheelus Air Force Base in Tripoli, Libya, mapping the desert for two years flying de Havilland Canada DHC-3 Otter, Beaver, Birddog and OH-23 Raven aircraft as an instructor pilot and unit test pilot.
His next overseas tours were flying over thousands of square miles of previously unmapped mountains and jungles in Central and South America. For this mission, he was based out of Howard Air Force Base, Panama, and Costa Rica. While assigned to the 11th Air Assault Division, Crandall helped develop air-assault tactics as a platoon commander. In early 1965, he joined the Dominican Republic Expeditionary Force as a liaison to the 18th Airborne Corps.
Later that year, he would command the 1st Cavalry Division's Company A, 229th Assault Helicopter Battalion at An Khe, Vietnam. Using the call sign "Ancient Serpent 6," he led a flying unit supporting eight battalions on the ground.
On 14 November 1965, Crandall led the first major division operation of air mobile troops into Landing Zone X-Ray in Vietnam's Ia Drang Valley for the Battle of Ia Drang and is credited with evacuating some 70 wounded comrades with his wing man and fellow Medal of Honor recipient Major Ed Freeman. The two also flew in the ammunition needed for the 7th Cavalry to survive. The craft he was flying was unarmed.
In January 1966, during the first combined American and South Vietnamese Army operation, "Operation Masher", Crandall, while under intense enemy fire and with only a spot flashlight beam to guide him, twice dropped his Huey helicopter through the dense jungle canopy to rescue 12 wounded soldiers. For his courage in that incident Crandall received the Aviation & Space Writers Helicopter Heroism Award for 1966.
After an assignment in Colorado, he attended the Armed Forces Staff College. Soon he was back in Vietnam, this time flying Huey gunships - "a big improvement" -- supporting the 1st Battalion, 9th Cavalry Squadron, 1st Cavalry Division.
In January 1968, four months into his second tour, Crandall's helicopter was downed during another rescue attempt due to Air Force bombs going off too close to where he was flying. After five months in the hospital, with a broken back and other injuries, he resumed his career as a student earning a bootstrap degree through the University of Nebraska in 1969. In Bangkok, Thailand, he would become a facility engineer managing 3800 people. He subsequently served as deputy chief of staff, deputy installation commander, and commander of the 5th Engineer Combat Battalion, all at Fort Leonard Wood, Missouri.
South America was supposed to be his next assignment, and he and his wife, Arlene, attended the Defense Language Institute, Monterey, California. as Spanish language students in preparation as aviation and engineering adviser to Argentina - an assignment that never came. A stroke sidelined Crandall, ending his flying career. After his recovery, the Crandalls did find the language training useful when he was sent to Caracas, Venezuela, as the Defense Mapping Agency's director for the Interamerican Geodetic Survey.
In his final Army assignment, he served as senior engineer adviser to the California Army National Guard.
Crandall retired from the Army in 1977 as a lieutenant colonel.
In 1994, Crandall was inducted into the United States Air Force's "Gathering of Eagles" - an organization set up to recognize pioneers of aviation and heroic flyers.
In 2001, Crandall was an aviation consultant on the movie We Were Soldiers about the Battle of Ia Drang. The movie, based on the book "We Were Soldiers Once...And Young" was released in 2002. Crandall was portrayed in the film by actor Greg Kinnear.
In 2004, Crandall was inducted into the Army Aviation Hall of Fame.
On 26 February 2007, Crandall received the Medal of Honor from President George W. Bush in a ceremony in the East Room of the White House.
He resides with his wife in Port Orchard, Washington.
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