This chapter deals with some significant and mutually dependent reasons behind Colombia’s and Trinidad’s immigration policies in a comparative perspective, focusing on the role of antisemitism, and imperial and monetary interests. Through an analysis of both oral history and historical documents, it takes a microhistory approach, drawing on the life histories of Austrian Jewish refugee families who fled from Europe to the Southern Caribbean to explore and illustrate the macrohistoric characteristics of Colombia’s and Trinidad’s immigration policies and their interconnections in the global context of the Second World War.