Leland Kennedy received his commission through the Air Force ROTC program at the University of Kentucky, Lexington. During the Vietnam War, Lieutenant Colonel Oliver O’Mara, Pilot of a second HH-3E of the 38th ARRS involved in the mission for which Leland Kennedy received his first Air Force Cross, was also awarded the Air Force Cross for his own role in the rescue effort. In a mission fifteen days later, Captain Kennedy earned a SECOND Air Force Cross, becoming the FIRST of THREE men (including Captain John Dramesi and Lieutenant Colonel James Robinson Risner) to earn TWO awards of the Air Force Cross. That accomplishment is only exceeded by the THREE Awards presented to Major James Kasler. Kennedy flew 99 missions in Southeast Asia, totaling 354 hours of combat flight time. He retired as a U.S. Air Force Colonel in 1985.