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Political theorists have long recognized that the 1960s mark a critical shift in CLR James’ mature political thought, from romantic or vindicatory accounts of anticolonial agency to more critical accounts of postcolonial tragedy (Scott 2004). This paper reinterprets James’ critical turn by characterizing it as a product of wider collaborations with the Trinidadian Oilfield Workers’ Trade Union (OWTU) and Sugar Workers’ Study Group to diagnose the ambivalences of economic development and the distinctive forms of state capitalism emergent in the early postcolonial Caribbean. For such actors, negotiations by postcolonial elites to establish a West Indian Federation (1958-60) were welcomed as the most promising political form to enable long-awaited programs of land reform, reforms that would ultimately enable more radical departures from colonial patterns of political economy (Paget 1992; Taylor 2018). Equally, the implications of federation’s collapse were most immediately visible in the efforts of government of Eric Williams to maintain labor peace across Trinidad & Tobago’s sugar plantations and oilfields, not least through projects of law and state repression like the Industrial Stabilization Act (ISA) that sharply curtailed the rights of independent labor organization. Reading James’ revisiting of the post-revolutionary reinstatement of compulsory labor in his revisions to the Black Jacobins and essays like the “Black Sans-Culottes” alongside organizing claim of OWTU, that the ISA stood for “in” or “is slavery again” illuminates their collaborative efforts to theorize role of postcolonial states in the reproduction and entrenchment of (neo)colonial patterns of political economy. At the same time, I argue that reconstructing this collaboration shows how James sought to generalize and extend existing practices of radical labor organization to imagine a form of the postcolonial mass party as an agency for social disalienation and democratic planning.