Charles Aloysius May

Lieutenant General Charles Aloysius May Jr.
U.S. Air Force Academy Class of 1959
Cadet Squadron 03

Lieutenant General Charles "Charlie" Aloysius May Jr. holds a distinguished place in American military history as a member of the United States Air Force Academy’s inaugural Class of 1959. A native of Washington, D.C., and a 1955 graduate of Archbishop Carroll High School, Charlie’s journey to the Academy was driven by a desire to lead during the dawn of the supersonic age. As a member of "The First Class," he helped establish the traditions and rigorous standards that define the Academy today.

Following graduation, General May’s career was defined by strategic vision and exceptional airmanship. After earning his pilot wings at Reese Air Force Base in 1960, he initially served as an instructor pilot, a role that would recur throughout his career. His passion for education and policy led him to the Air Force Institute of Technology (AFIT), where he earned a master’s degree in international relations from Columbia University in 1967. This academic foundation served him well during two separate tours as a faculty member at USAFA, where he inspired future generations of officers as an Associate Professor of Political Science.

In 1969, General May volunteered for combat duty in Southeast Asia. Stationed at Da Nang Air Base, South Vietnam, he served as the wing standardization and evaluation adviser to the VNAF 41st Wing. Flying the A-37 Dragonfly, he completed 165 combat missions, earning the Bronze Star and multiple Air Medals for his bravery and precision in support of ground forces.

The latter half of his 33-year career saw him ascend to the highest levels of the Strategic Air Command (SAC) and the Air Staff. A command pilot with over 5,400 flying hours, he commanded the 337th Bombardment Squadron, the 11th Strategic Group in the UK, and the 92nd Bombardment Wing. His leadership was pivotal during the Cold War’s final decade, particularly in his roles overseeing ICBM modernization and advanced programs. General May culminated his service as the Assistant Vice Chief of Staff of the Air Force, retiring in 1992.

In his "second career," Charlie remained deeply involved in the defense and veteran communities. He served as a commissioner on the Defense Conversion Commission and spent years as a director for the Air Force Retired Officer Community (Falcon’s Landing), ensuring that those who served were cared for in retirement. Known for his keen intellect and unwavering dedication to the "Long Blue Line," General May’s legacy is etched into the very foundations of the Academy he helped start.

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SERVICE ASSIGNMENTS
Years Duty / Assignment Location
1955–1959 Cadet, United States Air Force Academy Lowry AFB / Colorado Springs, CO
1959–1960 Student, Primary & Basic Pilot Training Bainbridge AB, GA / Reese AFB, TX
1960–1963 Instructor Pilot (T-29), 3566th Navigator Tng Sq James Connally AFB, TX
1963–1965 Flight Instructor (T-29/T-39), Instrument Pilot School Randolph AFB, TX
1965–1967 Graduate Student (AFIT), Columbia University New York, NY
1967–1969 Instructor, Department of Political Science USAFA, CO
1969–1970 Wing Stnd/Eval Advisor, 41st Wing (VNAF) Da Nang AB, South Vietnam
1970–1972 Associate Professor of Political Science USAFA, CO
1972–1973 Student, Air Command and Staff College Maxwell AFB, AL
1973–1975 Action Officer, Directorate of Plans Headquarters USAF, Washington, D.C.
1975–1978 Commander, 337th Bombardment Squadron Dyess AFB, TX
1979–1981 Deputy Commander for Ops / Group Commander 11th Strategic Group, RAF Fairford, UK
1981–1982 Wing Commander, 92nd Bombardment Wing Fairchild AFB, WA
1982–1984 Director of Training / Director of Command Control HQ Strategic Air Command (SAC), NE
1984–1987 Deputy for Strat Forces / Special Asst for ICBMs Headquarters USAF, Washington, D.C.
1987–1988 Deputy Dir of Advanced Programs (Acquisition) Headquarters USAF, Washington, D.C.
1988–1990 Deputy Chief of Staff for Requirements HQ Strategic Air Command (SAC), NE
1990–1991 Assistant DCS, Plans and Operations Headquarters USAF, Washington, D.C.
1991–1992 Assistant Vice Chief of Staff Headquarters USAF, Washington, D.C.

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MEDALS AND AWARDS
• Air Force Distinguished Service Medal (with 1 Oak Leaf Cluster)
• Legion of Merit
• Bronze Star Medal
• Meritorious Service Medal (with 2 Oak Leaf Clusters)
• Air Medal (with 6 Oak Leaf Clusters)
• Vietnam Service Medal
• Republic of Vietnam Gallantry Cross with Palm