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Homelessness remains a persistent urban crisis despite decades of policy reform and the growing prominence of housing-first approaches. While extensive research demonstrates that housing-first programs effectively stabilize individuals and reduce returns to homelessness, far less attention has been paid to the political conditions required to sustain pro-housing agendas over time. This study examines the political trajectory of homelessness policy in San Diego to explain why a city that formally adopted a housing-first framework in 2009 shifted in 2023 to an enforcement-oriented encampment ban paired with a municipally sanctioned outdoor camping site. We argue that this shift reflects a fundamental misalignment between policy horizons and political horizons. Pro-housing strategies operate on long timeframes, requiring sustained investment in affordable housing supply, service coordination, and system transformation. Although housing-first interventions can produce rapid stabilization for individuals, reducing homelessness at the citywide level involves cumulative and diffuse benefits that are difficult to attribute to specific political actors. In contrast, visible unsheltered homelessness—particularly downtown encampments—produces immediate and highly salient political pressures. Enforcement policies can quickly reshape public space and signal responsiveness to voters, residents, and business interests, even if they do not address structural causes. Drawing on city documents, public comments, media coverage, and interviews, we show how downtown property and business interests mobilized crisis narratives and privately collected homelessness data to compress the temporal frame of debate. By framing encampments as urgent threats to economic vitality, tourism, and public safety, these actors rescaled homelessness from a long-term structural condition to an immediate emergency demanding swift action. The malleability of the term “housing first” further enabled policymakers to claim continuity with pro-housing principles while pursuing criminalization measures. We conceptualize homelessness politics as a politics of temporal scale and demonstrate how short-term political incentives can destabilize long-horizon policy commitments.