Purpose: In recent years, a new wave of teacher-led political action has erupted resulting in work stoppages in several states across the United States. This study examines how superintendents navigated this Red for Ed movement in two representative states. Methods: Framed as a multisite, embedded case study, we drew from public documents and semistructured interviews with superintendents. We took a deductive approach to data analysis, seeking analytic generalization to the theoretical frameworks adopted herein. Findings: Red for Ed-motivated teacher job actions did create a political dilemma for superintendents. Superintendents addressed the dilemma by utilizing the roles of business manager, instructional leader, and politician as expressed through symbolic politics including assigning responsibility and vaguely supporting the Red for Ed cause. Superintendent responses are consistent with isomorphic tenants of sociological institutionalism. Implications: Considering the modern superintendency's political nature, superintendents might benefit from preparation in political strategy and tactics.