Harold Oscar Levy (December 14, 1952 – November 27, 2018) was an American lawyer and philanthropist who last served as the executive director of the Jack Kent Cooke Foundation. Having previously held leadership roles as a corporate attorney, venture capital investor and as a manager in the financial services industry, Levy is best known for having served as Chancellor of the New York City public schools, the largest school system in the U.S., from 2000 to 2002.