This paper examines how infrastructure redesign might both advance and draw critical direction from broader disciplinary realignments in support of just transitions—an umbrella movement rooted in the interconnectedness of socio-ecological systems. Across the United States, elevated urban highways built during postwar urban renewal have outlived the conditions that produced them, with escalating costs and enduring legacies of demolition and displacement. Through the case of SR-65, an elevated highway constructed through Pittsburgh’s Manchester community, we interrogate the violent origins of the highway's construction, ongoing debates surrounding its future, and offer speculative scenarios for its repurposing as multivalent socio-ecological infrastructure. Rather than prescribing a singular masterplan, the paper employs long-term, scenario-based methods developed through Carnegie Mellon University'sDesign for Transitionsstudio. The paper contributes to broadening discourse around aging infrastructure while demonstrating how architectural design might be situated in support of just transitions toward reparative, convivial, and regenerative urban futures.