Libby Massey

Managing Deputy General Counsel

Chicago Public Schools

Libby N. Massey is the Managing Deputy General Counsel in the Chicago Public Schools Law Department. In this role, Libby reports directly to the General Counsel and supervises the managers of the Department's Labor and Employee Discipline Unit, the School Law Unit, the FOIA Unit, and the Education Policy, Records, and Ethics Unit. Prior to this role, Libby served as Deputy General Counsel over the Labor and Employee Discipline Unit for four years, where Libby supervised a team of attorneys who prosecuted employee misconduct and termination cases and represented CPS in labor arbitrations and unfair labor practice charges. She also provided counsel on labor and discipline matters to schools, executive leadership, and the Board of Education. Libby has served in the CPS Law Department for about ten years, first serving as a law clerk, then Assistant General Counsel, Senior Assistant General Counsel, and Deputy General Counsel before being promoted to her current role. Libby is a 2023 graduate of the University of Chicago's Civic Leadership Academy where she earned a Certificate in Civic Leadership. Libby has a B.A. in International Relations and Political Science from the University of Wisconsin-Madison and a J.D. from the DePaul University College of Law with a certificate in Public Interest Law.