Like many YMG students and alums, Courtland Milloy began his career as journalist in high school. He first began writing for newspapers in 1967, employing the tools he picked up from his father, who taught journalism and graphic arts, and his mother, who taught typing and shorthand, both at Booker T. Washington High School in Shreveport, Louisiana.

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Milloy attended Louisiana State University and Southern Illinois University before going to work for the Miami Herald. In 1975, he left for The Washington Post where he reported on crime and politics. Milloy became a columnist for the Post in 1983 and he continues to write weekly perspectives on a range of subjects, with of focus on issues affecting the African-American community in and around the District.