The article examines the subject of homegrown violent extremism related to militant Islamism in the dual-Island Caribbean state of Trinidad and Tobago (T & T). It employs original research drawn from a series of semi-structured interviews and focus groups conducted between November 2015 and January 2016. Tracing the evolution of endogenous forms of radicalism and extremism the article considers how globalized-exogenous forms of militant Islamism associated with Al Qaeda and its offshoots, such as the so-called Islamic State, have impacted local patterns of violent extremism. The case study draws attention to a state and a region that have received scant attention in terrorism studies. As demonstrated by the article, this oversight is imprudent. There are a number of noteworthy findings from this case study for terrorism studies scholars: the unique historical legacy of radicalism, extremism and insurrection among T & T’s Islamists, the country’s markedly high levels of extremist travelers on a per capita basis and the high rate of religious converts among those travelers, the inter-linkages between criminality and political violence, and the potential threat posed by Trinidadian and Tobagonian militancy regionally.