The crime rate in the Caribbean is of paramount importance to politicians, government officials, and researchers. The World Bank notes that the region has the highest murder rate in the world (World Bank, 2008). Understanding the causal factors of deviant behavior is critical to developing strategies to overcome this problem. Western theories may have limited applicability in explaining crime in the Caribbean (Bennett and Lynch 1996; Birkbeck 1999), given that these frameworks have not been thoroughly tested in this region (Birkbeck 1999). As a first step to testing a theory of crime in the Caribbean, this paper considers the historical context of the region as it relates to deviance. Historical data shows, an interplay between colonization, economic factors, education, and incarceration in Trinidad and Tobago. I argue that crime in Trinidad and Tobago is influenced by inadequate education, poverty, race, and coloniality. The objective of this paper is to further criminological theory by determining the applicability of Western theories outside the region in which they were created.