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When the Supreme Court declared the Affordable Care Act's Medicaid expansion to be optional for all states in June of 2012, it touched off a round of high-stakes political battles in state capitols around the country. Many of these battles broke down along predictable partisan lines, but a number of Republican-controlled states chose to move forward with expansion, often after a contentious process that pitted Republican governors against their co-partisans in the legislature. In other states where Republicans held power, expansion advocacy efforts struggled to gain traction, even with diverse advocacy coalitions that included business organizations. More recently, advocates have found that going directly to the voters with ballot initiatives offers a way to achieve expansion despite continued opposition from Republican elected officials. What makes expansion advocacy efforts successful in some states, but not others, and how has this changed through these different eras of expansion politics? In this paper, I draw on dozens of interviews with advocates and policymakers across a number of states dating back to 2015 to develop answers to these questions.