Of late, teachers unions have worked together with district management in new and notable ways. This paper examines the role of teachers unions in shaping the Together Initiative (TI), which seeks to increase autonomy and broaden decision making in urban schools in one northeastern state. In general, state-level union leaders have taken more consistently reform-oriented stances than those adopted by their district-level counterparts. We found that district-level union leaders supported TI's growth and were willing to work with district leaders to reform schools in districts where labor-management relations had been collaborative in recent years and in schools where union leaders trusted the principal. Where labor-management relations were less positive and the union viewed principals as more arbitrary, union leaders practiced more industrial-style leadership.