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After winning leadership of the Massachusetts Teachers Association (MTA) in 2014, a rank-and-file caucus organized for several long-haul goals. They won the Fair Share Tax, which immediately funded free community college. MTA supported local chapters’ strikes, leading to higher pay for paraprofessionals and more. How did this cadre accomplish these political goals? What challenges were overcome, and which new challenges have emerged? This paper argues that organizers invigorated participatory democracy within their union and, in turn, shifted the political economy of schools in Massachusetts. Using hours of participant observation, 30 interviews with leader-organizers, and a critical media analysis, I explore one way rank-and-file school workers organize for the long haul -- meaning how they organize for broad, lasting change from militant actions.