This article examines the professional career of Jerome Lefkowitz, a central figure in the history of the Taylor Law, New York's public sector collective bargaining statute. Mr. Lefkowitz helped draft the Taylor Law, and served as the first Deputy Chairperson of the New York State Public Employment Relations Board (PERB) from 1967 until 1986, and the agency's fifth Chairperson from 2007 until 2015. PERB is the state agency responsible for administering the provisions of the Taylor Law. Between his two tenures at PERB, Mr. Lefkowitz was Deputy Counsel for the Civil Service Employees Association, Local 1000, AFL-CIO. The article examines Mr. Lefkowitz's emphasis on pragmatism rather than explicit ideology in administering the Taylor Law and in his role as an attorney for a public sector union.