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Despite its failure to repeal and replace the Affordable Care Act, the Trump administration has nonetheless been able to pursue conservative goals regarding Medicaid retrenchment and reform administratively. In particular, the Centers for Medicare and Medicaid Services has approved several states’ Medicaid waiver requests to impose work requirements on recipients. While the Obama administration approved some conservative waiver proposals in its efforts to encourage more states to take up the Affordable Care Act’s Medicaid expansion, it drew the line at work requirements as contrary to the goals of the Medicaid program. This paper considers the politics of states’ pursuit of Medicaid work requirements in the context of the politics of the ACA and Medicaid more broadly. I conduct a content analysis of 1115 waiver submissions by states looking to expand Medicaid with conservative changes during the Obama administration, with a focus on what changes were proposed, which were accepted, and the rationale for these proposals and the Obama administration’s decisions. I then conduct a similar content analysis of state Medicaid waiver proposals submitted to the Trump administration. I trace how rationales developed by states applying for waivers under the Obama administration developed and were echoed by the Trump administration. Finally, I consider how these changes have produced policy feedback effects by drawing on public opinion data drawn from surveys conducted by the Kaiser Family Foundation as well as early accounts of how work requirements have been implemented. The results of this analysis are considered in the context of literature on policy feedback and the social constructions of target populations that undergird the stated rationales for proposed changes to Medicaid policy. In doing so, the paper builds on previous work that consider the policy feedback effects of Medicaid policy (Michener 2018) and Medicaid expansion (Hertel-Fernandez, Skocpol, and Lynch 2016; Grogan and Park 2017; Grogan, Singer, and Jones 2017), as well as connects previous, state-specific research on Medicaid expansion waivers (Katz Olsen 2015; Brasfield 2016; Flagg 2016). The paper concludes by considering the politics of Medicaid work requirements in the context of other programs for vulnerable populations, such as the Supplemental Nutrition Assistance Program, that have been subjected to retrenchment efforts via work requirement proposals.