This thesis project is a theoretical contribution to the field of Caribbean studies. It suggests that the state-led revolutions of the Caribbean in the twentieth century present as a tragedy because such revolutions--like the Grenada revolution--catastrophically collided with the system-limitations of the state. Thus, these revolutions present as a failure to transform society from the outset. However, the Caribbean scholarship still appears to include the state in prescriptive solutions towards transformation, therefore, a spirit of optimism around the state persists. Thus, this thesis throughly critiques past and contemporary Caribbean scholarship on the postcolonial state in an attempt to exorcise this spirit and move past the notion of the state as a locus of potential transformation for the region. In the critique, it is concluded that the scholarship has failed to grasp the state and twentieth century state-led revolutions in the Caribbean, noting that key to the maintenance of this statist spirit of optimism is their analytical separation between 'politics' and 'economics.' The thesis proceeds to present an alternative view of the state through Marx's critique of political economy and the dialectical reconstruction of the concrete in thought. In this critical mode of thought, I present the state and its relation to capital as immanently connected. The state is concluded to be fundamentally incapable of social transformation due to its genesis in the commodity form which determines specific system-limitations to its actions. It also suggests that the collision into these system-limits is the experience of the Caribbean. The failure to transform in the twentieth century Caribbean is the tragedy of state-led revolution manifest.