DescriptionSince Independence in 1962, Jamaican society has witnessed a substantial ebb and flow of dominating political ideologies. At the center of this political friction are the Premierships of Michael Manley and Edward Seaga. The former representing a turn to “democratic socialism” and the latter an alignment with neoliberalism, this dichotomy, I argue, segmented broad layers of the working class and radical political elements from galvanizing a movement that would have had a profoundly transformative effect on Jamaican society. This is particularly salient in examining Manley’s second stint as Prime Minister in which the neoliberal policies instituted by the government of Edward Seaga were generally continued. This paper argues that due to the process of constitutional decolonization, radical portions of the labor movement and radical political parties were unable to bring to fruition a society far removed from the status quo. Decolonization through the legitimizing legal processes of the British Empire rather than through violence hampered the development of radicalism in Jamaica that could challenge the ruling layers both in a domestic and international context. The fact that there was not a violent uprising against British rule (as seen in Kenya, Malay or Guyana) left little political space for radicals to participate in Jamaican civil society. Within the confines of Jamaican parliamentarianism, the Jamaican Labour Party and the People’s National Party had a veritable monopoly on political power, resulting in limited space for radical labor or political organizations. This paper examines the consequences of this lack of political maneuverability in the context of the Cold War.