Rear Admiral Flagg graduated from the Naval Academy in 1961 and in 1962 became a Navy pilot and started flying the F-8 Crusader jet. He had three tours of duty in Southeast Asia during the Vietnam conflict. He left active duty in 1967. He joined American Airlines and the Naval Reserves F-8 Squadron VF-201. He was commanding officer of Naval Reserve F-8 squadrons VFP 206 and VFP 6366. Here, Rear Admiral Flagg stopped flying the F-8 Crusader after having logged more than 3,200 flight hours on the F-8, one of only five to accomplish this feat, and more than any of the other four pilots. Rear Admiral Flagg was commander of the Naval Reserve Readiness Command Region II, and assistant chief of naval operations-air warfare. He was special assistant to the Honorable Fred Davidson, deputy assistant secretary of the Navy. He was tapped for flag rank in 1986 and received his first admiral’s star. In 1987 he was designated a rear admiral, and posted at the Pentagon as one of the top officers for the Naval Reserve. In 1990, Rear Admiral Flagg was awarded his second star. On October 15, 1993 he was censured for failing to prevent the 1991 Tailhook conference scandal, effectively ending further advancement. He retired from the Navy in 1995. He was also a captain for American Airlines, and retired from that occupation in 1998. He remained available for technical advice to the Pentagon.
In his military career he logged the most hours of any pilot on F-8 Crusader supersonic jets. After the war he flew photo reconnaissance missions.
The Flaggs moved to Millwood, Virginia around 1993 to start Daybreak Farm, a Black Angus beef cattle farm.
Flagg died at 62 in the crash of American Airlines flight 77 in the September 11, 2001 Terrorist Attack. He was traveling with his wife, Darlene "Dee" Flagg, and friend, Barbara G. Edwards, to Las Vegas at the time of the crash.
He is survived by two sons, Marc and Michael Flagg, and other family.
Tributes and Comments
See September 11, 2001 Terrorist Attack/Casualties.