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National policies for reducing poverty and inequality have received much scholarly attention but we know less about subnational determinants of conditional cash transfers that aim to break the intergenerational transmission of poverty through human capital investments in education and health. I focus on understanding why and when local politicians implement targeted antipoverty policies. Through a dynamic comparison of the neighboring Brazilian cities of Rio de Janeiro and Niterói in the time period 1992-2016, I find different trajectories of politician-poor voter interaction, in particular in relation to contingent (clientelist) exchanges of benefits like cash, food, and construction materials for political support. As clientelism became a political burden in Rio; campaign promises of CCTs became a tool for attracting nonpoor voters. Niterói did not have the same clientelist history, and its politicians throughout the case study period did not adopt CCTs despite having poverty and inequality levels close to those of its neighbor. Within the limitations of an observational study, comparing two similar cities across time provides nuance and fine-grained data that may improve our understanding of the politics and path dependency of pro-poor redistribution.