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Prison abolition is often dismissed as an impractical, unattainable dream or an elite-led, academic framework that is out of touch with popular sentiments on the ground. Challenging these myths, and joining abolitionist scholar-activists, we theorize abolitionist politics as a practice of pragmatic and locally situated imagination seeking to transform existing political, judicial, and community systems for the flourishing of the most marginalized. We draw from the case of Maine’s Justice Think Tank (JTT)—a collaborative initiative that consists of twelve incarcerated scholars researching transformative alternatives to the criminal legal system—to bring into view how, beyond proposing policy recommendations, abolitionist movements enact new visions (of safety, justice, restoration, responsibility, and accountability) that intervene into ordinary habits of perception and sentiment. In its effort to offer innovative solutions for local problems where most improvement is necessary, such as social learning, housing, food security, and access to employment, JTT builds new majorities that are concerned with public wellbeing and the efficacy of existing systems. In doing so, it materializes the democratic task of achieving “a life of free and enriching communion,” in John Dewey’s sense, a task that can be “accomplished only by inventive effort and creative activity.” As two members of JTT, one incarcerated fellow, one non-incarcerated faculty walk-along, we demonstrate that abolitionist practitioners continually navigate the dilemmas of strategy, enacting decarceral horizons while developing practical steps that aim to build public trust toward those horizons. This navigation, as an iterative process, generates original political and theoretical insights that are unbounded by, yet emergent from within, the existing conditions of carcerality.