For an unbroken twenty-two years, and unlike most of India's other states, West Bengal has been ruled by the Left Front, a coalition of communist parties. Much of the research on this region has been concerned with evaluating the Front's agrarian reformism. However, the question of poverty has rarely been broached. This dissertation is concerned with the politics of poverty, and how it can be understood at the rural-urban interface. Based on the unprecedented migration of rural landless households, I hypothesize that agrarian dispossession is linked to the emergence of a new set of gendered urban linkages. Starting in Calcutta's squatter settlements, and using life histories, I trace the survival strategies of landless migrants, originally from the South 24-Parganas district of West Bengal, as well as of daily commuters who have forged access to urban work, but not shelter. On this basis, I suggest that what is distinctive about these groups is not the dynamics of rural marginalization, but instead the persistence of poverty despite urban access. The ethnography of squatting and commuting points to a key dimension of persistent poverty: feminized livelihoods, where women as primary earners are limited to casualized segments of the urban informal sector. However, the dynamics of squatting reveal that urban poverty can only be understood through a logic of double gendering that inextricably links feminized livelihoods to masculinized politics. Here, squatting becomes a Faustian bargain that, negotiated through masculinist patronage networks, seals the dependence of squatters on fickle-minded political parties, and sutures family and regime. This study also suggests that the contradictions and possibilities of such a hegemonic project need to be placed within a particular historical moment of the Left Front. I designate this as "communism for the next millennium," a clumsy balancing act between old and new populisms that plays out in the volatile geography of Calcutta's suburbanizing fringes. The politics of poverty shows how, in contemporary West Bengal, hegemony is negotiated in gendered terms. The view from the rural-urban interface reveals the spatialities through which Calcutta is reproduced as a site of poverty.