Housing approximately half a million residents, the New York City Housing Authority (NYCHA) has long been cast as the exception to the rule of ‘demolish and replace’ models of public housing in the United States. Yet as NYCHA faces a dire fiscal and administrative crisis, it has proposed a suite of privatization efforts that threaten its successful reputation. With a focus on NYCHA’s effort to allow private developers to construct mixed-income ‘infill’ projects on existing ‘underutilized’ public housing land through the NextGeneration NYCHA and NYCHA 2.0 plans, in this dissertation, I ask: how do various stakeholders, including residents, the housing authority, private developers, elected officials, and non-profit and advocacy stakeholders justify, react to, and resist NYCHA’s plans for redevelopment? While most studies consider the impacts of mixed-income housing on residents after lease up of a development, interpreting it as either a de facto beneficial policy or as a tool for state-led gentrification, this work differs in its focus on the range of viewpoints about the plan prior to construction. In so doing, it straddles the literature on mixed-income housing and urban planning processes through the lens of pragmatism. A pragmatic approach centers those most impacted in planmaking and considers how diverse stakeholder experiences co-exist and contrast in public deliberation processes. In other words, this dissertation considers how the housing authority’s various publics have reacted differently to the plans for its transformation with the goal of informing how to craft more restorative, equitable, and deliberative planning processes. Using data from over a year and a half of participant observation, interviews, and media and policy sources, I craft a qualitative narrative case of the deliberations surrounding NYCHA’s first five years of redevelopment from a variety of stakeholder perspectives. Using narrative and framework analysis, I organize this dissertation around three empirical chapters: 1) an anatomy of the formal and dialogical channels of engagement between speakers and NYCHA officials at 10 public meetings following the NextGeneration NYCHA plan’s release; 2) an account of the housing authority’s stop-and-start approach to pursuing infill set amidst its various crises, including an analysis of the viewpoints of public officials and a private developer selected for a pilot infill site; and 3) a description of residents’ opposition to the plan, which includes descriptions of spaces of contestation citywide and at a specific pilot infill development on the Upper East Side of Manhattan. I find that while multiple stakeholders agree on the end goal of repairing existing public housing, actors promote a series of contradictions in their means to fix it, shaping a hotly contested landscape that has eroded public trust and further delayed action. Despite critiquing the housing authority for their management practices, residents launched a campaign to keep their homes publicly-operated that extended beyond the walls of their developments to citywide and even national progressive issues. This dissertation contributes to the housing policy and urban planning literature in three ways. First, it proposes an understanding of mixed-income housing that eschews past binary approaches and shows its perceived benefits and risks as highly dependent on the values and goals of the stakeholder. Second, it looks at conflicting attitudes to planmaking outside of a traditional consensus-based models, inviting a contextual understanding of power dynamics while also placing value on the experiences and actions of the majority Black and Latinx public housing residents who are the most impacted by the infill plans. Lastly, this dissertation also serves to profile pragmatism’s power–and limits– for theorizing more equitable redevelopment processes in planning.