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Tom Bailey was born in Winston-Salem, North Carolina. He graduated from high school in 1963 and enrolled at North Carolina A&T State University. After two years, he left the school intending to join the Peace Corps, but instead took a job with a poverty program in Winston-Salem. In 1967 he re-enrolled at A&T. While there, Bailey was involved with YES (Youth Education Services) until it dissolved in ’68, the FCD (Foundation for Community Development), and GAPP (Greensboro Association of Poor People). Bailey moved to Davidson County in 1969 to work as executive director of a poverty program. Later that year, he began work as director of community development for the Office of Economic Opportunity (OEO). After the A&T cafeteria workers’ strike in 1969 and the board of education cafeteria workers’ strike in 1970, he resigned from OEO and worked again for GAPP.