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This article is a critique of Nairobi city’s socio-political histories as portrayed in Kenyan literary works of the 1970s, focusing on Mwangi Gicheru’s Across the Bridge (1979), Charles Mangua’s Son of Woman (1971), Meja Mwangi’s Going Down River Road (1976) and The Cockroach Dance (1979). The article conveys insights on urban castaways by reading the city as a canvas onto which novels reconfigure the nation’s histories that feature through various characters who impress their hopes, aspirations, desires upon a city that is indifferent to them. It engages with Nairobi castaways’ fictional realities but links them to Nairobi’s social histories. The focus is on slum demolitions, the persistence of colonial vagrancy laws, which also informs state operatives’ insistence on expelling Nairobi castaways from slums for them to return to their presumed ancestral homes in rural areas. The demolitions and expulsions appear a simplistic way to navigate city aesthetics, to tackle congestion and crime. The article advances the argument that the plight and persecution of Nairobi castaways as portrayed in the selected literary works and in reality is exacerbated by the Kenyan government’s historically uncritical adoption of neo-liberal capitalism, an offshoot of colonial capitalism. Indeed, the selected novels reveals the novelists’ critical assessment and exposure of the underlying exploitations of marginalised urbanites by both local and foreign neoliberal capitalists.