Born in Springfield, Illinois and son of a career United States Navy Chief Petty Officer he attended high school in Jacksonville, Florida and was awarded a football scholarship to The Citadel in Charleston, South Carolina where he won the starting quarterback job his sophomore year until sidelined with a knee injury; he is an initiate of the Theta Commission of the Kappa Alpha Order. Rosa entered the Air Force in May 1973 after receiving his bachelor's degree and his commission (via Air Force ROTC); he earned a master's degree in public administration from Golden Gate University in 1985. Rosa is also a graduate of the Air Force Squadron Officer School, Air Command and Staff College, U.S. Army Command and General Staff College, U.S. Army War College and the Program for Senior Executives in National and International Security Management, John F. Kennedy School of Government, Harvard University.

After his commissioning, Rosa went to pilot training at Craig Air Force Base, Alabama, followed by fighter training at Holloman Air Force Base, New Mexico. He flew the LTV A-7 Corsair II and Fairchild Republic A-10 Thunderbolt II with the 354th Tactical Fighter Wing at Myrtle Beach Air Force Base, South Carolina then the General Dynamics F-16 Fighting Falcon with the 56th Tactical Fighter Wing at MacDill Air Force Base, Florida; from 1980 to 1983, he served an exchange tour with the Royal Air Force as a pilot in Hunter and Jaguar aircraft at RAF Lossiemouth, Scotland.

His command positions have included the 35th Tactical Fighter Squadron, Kunsan Air Base, South Korea; the 366th Operations Support Squadron, Mountain Home Air Force Base, Idaho; 49th Operations Group at Holloman Air Force Base, New Mexico; 20th Fighter Wing, Shaw Air Force Base, South Carolina; and the 347th Rescue Wing, Moody Air Force Base, Georgia. He has also served on staff assignments at Pacific Air Forces, U.S. Air Force headquarters, and was Deputy Director for Operations on the Joint Staff. He also served as Commandant of the Air Command and Staff College and concluded his military career serving as the sixteenth Superintendent of the United States Air Force Academy before retiring from the Air Force in 2005.

Rosa is a Command Pilot with more than 3,600 flying hours in the A-7, A-10, the Hunter and Jaguar aircraft, F-16, F-117A, HH-60G and HC-130; he also attended the Instructor Course of the USAF Weapons School.^[5]

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