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Gregory was bussed across town to attend an all-black school until eighth grade, when schools in his town were integrated. The sacred status of education in the Gregory family was vividly demonstrated one day when students staged a boycott to protest the integration and townspeople said that they would remove black children from the school. The young Gregory attended anyway and was the only student to show up for his class. Despite facing taunts from white students while in high school, Gregory did well and during that time further developed his interest in entering the military service. After becoming a member of the Junior Reserve Officers' Training Corps (ROTC), he was introduced to military aircraft during visits to nearby Andrews Air Force Base in Maryland and was soon hooked on flying.
In the 1950s Gregory met a member of the Thunderbirds, an Air Force acrobatic flying team, who told him about the new United States Air Force Academy about to open its doors in Colorado Springs, Colorado. Gregory was interested, but decided to stay with family tradition and apply to Amherst College, where his grandfather had attended. Luckily, his father intervened to help the young man do what he loved. Against the odds, the elder Gregory persuaded U.S. Representative Adam Clayton Powell of Harlem to sponsor his son's application. When Fred Gregory enrolled in the U.S. Air Force Academy in the early 1960s, he was the only black in his class. Occasional resistance against his presence on campus did not affect his performance, however, and he excelled as a cadet, student, and athlete. Gregory graduated from the academy in 1964, in a class that produced 25 generals.
Upon graduation, Gregory hoped to become a teacher of military history at the academy or an engineer, but he opted for helicopter flight training at Stead Air Force Base in Nevada because he thought his subsequent assignments would be more pleasing to his wife. He was given his wings in 1965, and after serving as helicopter rescue pilot at Vance Air Force Base in Oklahoma, was shipped to Vietnam to serve as a combat rescue pilot. His primary duties as pilot of an H-43 helicopter in Vietnam were search and rescue and fire suppression. Gregory was awarded a Distinguished Flying Cross in 1967 for rescuing four Marines from a downed helicopter during intense enemy fire.
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