Since Critical Rationalism is considered by some more of an attitude or mindset and by others a methodological approach to philosophical thinking and practical problem-solving, its application, or more accurately, its epistemological testing grounds, should be expected to be much more wide-ranging than they have been so far. With the exception of some published anthologies on Critical Rationalism and occasional nods to the legacy of Karl Popper’s falsificationist methodology, relatively few applicaions of a critical rational approach to contemporary theoretical debates in the social sciences have been published. I wish here to critically challenge the (optimistic) Hegelian and by extension the neoliberal view of the progress of American capitalism by reframing it with the Marxian notion of expropriation as applied to enslavement on plantations. The logic of enslavement as a process by which brutal exploitation has been practiced for centuries offers a falsifying test case of the rationality of capitalism and its promise of individual freedom of choice. This essay is an explicit exercise in the potential power of a version of Popperian critical rationalism being applied to the intersection of modern liberalism and capitalism, exploring the imbrication of a critical and rational analysis.