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Cities have been lauded as sites of robust local democracy and participation, mobilization and contestation, and claims-making and (re)distribution, especially where they are characterized by significant socio-economic inequality and segregation. Yet when do local elections facilitate patterns of representation that reduce these inequalities or, at the very least, deliver policies that explicitly benefit the urban poor? In this project, I develop a set of “local democratic pathologies” that operate in decentralized cities—i.e., programmatic, management, enclave, and fiefdom—that characterize urban politics as a function of the electoral drivers and support coalitions that bring local mayors to power. The core independent variables of interest are (1) whether voters rely on strong class-based partisan heuristics when casting ballots for district mayors or rather preference local concerns and candidate qualities and (2) the competitiveness of local elections, associated with partisan blowouts or strong incumbency advantages. I link each pathology to a set of benefits and weaknesses so far as local representation is concerned and discuss the relative preferences that richer and poorer voters are likely to have over the set of pathologies. I collect district level demographic and electoral data from Buenos Aires, Bogota, Lima, Mexico City, and Santiago to classify these cases into likely pathologies. I also use more disaggregated data—e.g., city bloc socio-demographics and polling station election returns—to conduct simulations and consider counterfactuals that might emerge conditional on whether these cities were less segregated, redistricted, or characterized by different electoral institutions and partisan dynamics.