Leonard began his career as the assistant dean of the Howard University School of Law in 1968. He worked on the Harvard Plan, "one of the country's earliest and most effective affirmative-action programs, which became a model for other universities around the country." He fundraised $12 million, Donaldson accepted the resignation; however, Leonard was asked to serve as president until the end of the academic year of 1983–1984. Leonard was a "distinguished senior scholar" at his alma mater, Howard University, from 1984 to 1986, executive assistant to the governor of the
U.S. Virgin Islands from 1987 to 1989, and the executive director of
Communities in Schools from 1990 to 1994. ==Personal life, death and legacy==