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Since 2011 billionaire funded organizations, like the Freedom Foundation, have turned their attention to suppressing public sector union membership. Florida stands alone among Jim Crow states for guaranteeing public sector collective bargaining in its state constitution. However, bills to work around this guarantee have been proposed in the legislature year after year, with only limited success. The breakthrough occurred in 2023 when a supermajority Republican legislature, along with a determined and influential governor, passed Senate Bill 256, creating new obstacles to creating and maintaining public sector unions in Florida. This resulted in the decertification of more than 120 unions, including the state workers’ union, undermining what little labor protections they have in Florida. Using ethnographic and qualitative immersion methods I examine the political struggle that occurred over SB 256, between business interests and labor unions. I argue that this battle and past battles over public sector collective bargaining have occurred on the terrain of class struggle, but that the results of past battles have resulted in institutionally weakening the political position of public sector unions. As a result, unions have been limited to lobbying techniques that, while reasonably effective, were unable to stave off further repression when confronted with a determined legislature. This article shows how the political struggle over anti-union legislation turns into one side dominating the other, leaving unions to beg hostile legislators to spare them for one more year.