To write this paper we shall engage in a spot of time-travel: It is ten years in the future and Cuba, after the death of Fidel Castro, is aggressively moving to join the capitalist world. As a part of modernizing and expanding its economy, the new government of Cuba is considering joining NAFTA, the North American Free Trade Alliance. This paper provides a brief overview of the reasons why Cuba might – or might not – want to join NAFTA.