He made his way through college during the economic depression working odd jobs and singing in bands. In 1935, Cochran graduated from Ohio State University. He entered Army pilot training in 1936 and graduated to P-6s with the 33rd Pursuit Squadron on the 8th Pursuit Group at Langely Field, Virginia. In four years, Cochran rose from flying cadet to Squadron commander of the 33rd.
Early in World War II, he played a major role in the build up of fighter squadrons and the development of tactics to match the new fighters. Cochran worked with fellow fighter leader Johnny Alison. He also spent time with the famed cartoonist Milton Caniff, who wan an Ohio State graduate as well. Caniff based his Terry and the Pirates character "Flip Corkin" on Cochran.
During Operation Torch in North Africa, Cochran led the "Joker Squadron of the 33rd Fighter Group in Army P-40s off the British carrier Archer. Later he led the 58th Fighter Squadron of the 33rd Group in combat throughout North Africa. Colonel Cochran helped train and introduced into combat the first all-black 99th Fighter Squadron. He left North Africa with a reputation as a proven Unorthodox combat leader.
His North Africa fame earned him the attention of General "Hap" Arnold. General Arnold picked Cochran and Alison to lead project NINE, later called the 1st Air Commando Group. The top secret mission of this composite group was to support British General Orde C. Wingate and his "Chindits" in Burma. Together, as part of Operation Thursday, the Chindits and Air Commandos accomplished the first actual night combat airfield seizure operation when they assaulted a jungle clearing and built "Broadway" air strip 165 miles behind Japanese lines. Nine Thousand troops and tons of supplies were airlifted into "Broadway" in five days. The Air Commando composite force of fighters, bombers, transports, gliders, light planes and helicopters provided reconnaissance, combat air patrol, air landing, air lift, interdiction, close air support, resupply, and medevac to the Chindit force.
Colonel Cochran later played a part in planning the invasion of France and Germany. He retired from the military in 1946 for health reasons. As the U.S. Air Force came into being, Milton Caniff started a new comic series called Steve Canyon, in which Cochran was the role model for the character "General Phillire."
Cochran worked for Howard Hughes' RKO Movies as an aviation advisor. He managed some of the first jet filming ever attempted while flying copilot in a B-47 camera ship for the movie "Jet Pilot." Later he returned home to Erie to serve in his brother's business, Lyons Trucking. Over the years he rose to president of Lyons and help expand it into a nationwide company. As an avocation he took to riding and breeding horses. He died on horseback of a heart attack during a fox hunt at age 69.
Cochran also became active in charitable organizations such as the Pennsylvania Heart Association. He was a consistent supporter for Erie's Gannon University, and attended many USAAF reunions.
Cochran dated actress Betty White in the early 1960s after being introduced by Jack Paar. White declined his marriage proposal; later dating Cochran and her future husband Allen Ludden simultaneously, until her romance with Ludden became serious.