Charles Gillespie was born on February 24, 1929, in Meridian, Mississippi. He was commissioned through the U.S. Naval Academy on June 1, 1951, and completed flight training, earning a designation as a Naval Aviator in 1952. He served in numerous flying assignments before flying combat missions in Southeast Asia with Fighter Squadron 151 off the aircraft carrier USS Constellation (CVA-64) from June to November 1966 and then off the aircraft carrier USS Coral Sea (CVA-43) from August 1967 until he was forced to eject over North Vietnam and was taken as a Prisoner of War on October 24, 1967. After spending 1,969 days in captivity, Capt Gillespie was released during Operation Homecoming on March 14, 1973. He was briefly hospitalized for his injuries and then served as a Test Pilot, Chief of Staff for Plans and Programs of the Naval Air Test Center, Commanding Officer of NAS Patuxent River, Maryland, and as Deputy Commander of the Naval Air Test Center at Pax River, from June 1975 through October 1982. Capt Gillespie's final assignment was as Director of the Range Directorate, Pacific Missile Test Center, in Point Mugu, California, from October 1982 until his retirement from the Navy on June 30, 1983. He died in the crash of a Mitsubishi MU-2 on February 28, 1989, and was buried at Arlington National Cemetery.

His Silver Star Citation reads:

For conspicuous gallantry and intrepidity while interned as a Prisoner of War in North Vietnam. On 24 October 1967, his captors, completely ignoring international agreements, subjected him to extreme mental and physical cruelties in an attempt to obtain military information and false confessions for propaganda purposes. Through his resistance to those brutalities, he contributed significantly toward the eventual abandonment of harsh treatment by the North Vietnamese, which was attracting international attention. By his determination, courage, resourcefulness, and devotion to duty, he reflected great credit upon himself and upheld the highest traditions of the Naval Service and the United States Armed Forces.