After receiving his commission in the Air Force as a second lieutenant and aeronautical rating as a navigator, General May entered primary pilot training at Bainbridge Air Base, GA., flying T-34s and T-37s. He then was assigned to Reese Air Force BAse, TX, where he completed T-33 training in September 1960 and earned his pilot wings. In October 1960, the general transferred to James Connally Air Force Base, TX, to fly T-29s. Later, he became and instructor pilot assigned to the 3566th Navigator Training Squadron's Instrument and Transition Section.
In April 1963, after completing the Instrument Pilot Instructor School program, he joined the staff of the school as a flight instructor in T-29s, an academic instructor and a T-39 pilot. Subsequently, General May was selected for the Air Force Institute of Technology graduate program at Columbia University, entering in 1965. After completing the course work for a Ph.D. and graduating with a M.A. two years later, he was assigned to the department of of political science at the Air Force Academy as an academic instructor. In April 1969, he volunteered for a combat assignment to Southeast Asia. After completing A-37 combat crew training at England Air Force Vase, L.A., he departed for Da Nang Air Base, South Vietnam for assignment as the wing standardization and evolution advisor to the 41st Wing of the Vietnamese Air Force. While in Vietnam, he flew 165 combat missions in the A-37.
He returned to the Air Force Academy in May 1970 as an associate professor of political science. In June 1972, the general was selected to attend to Air Force headquarters as an Air Staff action officer with duty in the Pacific-Southeast Asia Branch, Directorate of Plans, Office of the Deputy Chief of Staff for Plans and Policy, for the next two years.
After completing B-52 combat crew training at Carswell Air Force Base, TX in 1975, General May reported to the 96th Bombardment Wing at Dyess Air Force Base, TX. During this assignment, he served as a B-52 aircraft commander, operations officer and commander of the 337th Bombardment Squadron. In January 1978, he became the deputy commander of the 96th Combat Support at Dyess. The following summer he entered the North Atlantic Treaty Organization Defense College, graduating in 1979. He was then assigned to the 11th Strategic Group at Royal Air Force Station Fairford, England as the deputy commander for operations. In March 1980, he became the group commander.
From July 1981 to August 1982, he commanded the 92nd Bombardment Wing at Fairchild Air Force Base, WA. General May was then assigned to Headquarters Strategic Sir Command, Offutt Air Force Base, NB., as the director of training. In January 1983, he was promoted to brigadier general and became the director of command control.
Subsequently, he returned to Air Force headquarters to server as deputy for strategic forces, Directorate of Operational Requirements, Office of the Deputy Chief of Staff, Research, Development and Acquisition from October 1984 to July 1985. He was then assigned to the Office of the Deputy Chief Staff, Research, Development and Acquisition as the special assistant for ICBM modernization. The general later served as the deputy director of operational requirements as well as special assistant for ICBM modernization from February 1986 to March 1987. He then became the deputy director for strategic, airlift and training programs, Office of the Secretary of the Air Force Acquisition as the result of the implementation of the Goldwater-Nichols DoD Reorganization Act.
In June 1988, Major General May was reassigned to Headquarters Strategic Air Command in the newly created position of deputy chief of staff for requirements, acquisition and testing. He returned to the Pentagon in January 1990 as the assistant ot the deputy Chief of Staff for Plans and Operations. Thirteen months later, he was promoted to lieutenant general and assigned as the Assistant Vice Chief of Staff of the Air Force.
General May retired from active duty on July 1, 1992. He had earned the rating of command pilot with more than 5400 hours in various aircraft including B-52s, KC-135s, EC-135s, T-39s and A-37s. His military awards and decorations include the Distinguished Service Metal, Legion of Merit, Bronze Star Medal, Meritorious Service Metal with two oak leaf clusters, Air Medal with six oak leaf clusters, and numerous foreign awards.
Immediately after retirement from the Air Force, General May accepted a Senior Executive Service position as the only full time commissioner and Vice Chairman on the Congressionally mandated Defense Conversion Commission. He left that position in February 1993 when the Commission completed its work and issued a report to the President.
Since 1993, he has been self-employed as an independent consultant focusing on national security issues and business process re-engineering practices. His list of clients include: Global Associates; the State of Ohio; Burdeshaw Associates; Hughes SPace Communications; Sage Alliance; Information Analysis; Lockheed Martin Missiles and Space; AIL; Northrop Grumman; NA Rockwell; The Gimbal Group; Microdyne; Universal Power Systems; Strictly BUSINESS; Software Valley; AARP. General May is a member of the Board of Advisors to the Jewish Institute for National Security Affairs and a director for Information Analysis and the Air Force Retired Officers Community.