This paper explores the federal Race to the Top (RTT) and the New York State (NYS) Annual Professional Performance Review (APPR) educational policies and the ways in which unions are relevant to education in light of these policies. Teacher unions fight for better working conditions, whether it is for smaller classes, instructional teaming, or adequate time for lesson planning, etc., which has the goal of improved student learning. Teacher unions affect the future of both the institution of organized labor and the foundation of public education. This paper is an in-depth look at how a union works and what union representatives’ experiences are in today’s era of high teacher-accountability. Six union presidents were interviewed to help understand this phenomenon. From coding there were fifteen themes that emerged from the interviews. The themes suggest that union presidents: elevate the profession; make schools better places for teaching and learning; confront people in a professional way; make the union transparent; calm people down; understand the dynamics of teaching; make decisions that benefit the majority of the members; recognize the long-term implications of decisions made; protect the collectively bargained agreement; defend teacher rights; realize that it is the priority of management to dismiss ineffective teachers and not the unions; and hold teachers accountable. Furthermore, the generalization of a few bad teachers hurts the profession. Also, there are many issues that arose with the newly implemented APPR.