Findings from a study that explored the role changes and stresses experienced by superintendents in school districts undergoing school and union restructuring are reported in this paper. Methodology involved interviews and field investigation in five cities--Pittsburgh, Cincinnati, Louisville, Miami, and Rochester. New superintendent roles included recognizing the need for change, developing an organizational view, engaging in new labor relations roles, and creating new allies to mobilize political and financial support. Findings indicate that, due to changing school board membership and ideology, the superintendent/union alliance is inherently unstable and is therefore insufficient in itself to sustain lasting restructuring. (31 references) (LMI)