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The political fortunes of teachers’ unions have changed dramatically in recent years. Although these changes have an enormous impact on the kinds of laws that are enacted in the new policy arena, we know little about them. In response, I offer case study analysis of a Massachusetts law passed in 2012 that limits seniority-based tenure for public school teachers. Unprecedented in the state’s history, the law was a compromise between the state teachers’ union and a controversial non-profit advocacy group. I use policy cycle theory to explore internal struggles over how the union should respond to political conflict, and I demonstrate that union leaders faced a variety of pressures that ultimately led them away from the concerns of rank-and-file membership.