As in many non-democratic regimes, widespread illegality coexists alongside relatively good security in Cuba. Economic and political liberalization are highly desirable, and can entail significant benefits for the population. However, the process is not without danger. This book examines Cuba's present security conditions and forecasts the effects liberalization could have on the people of Cuba.

Cuba has a privileged geographical location, one that can be exploited for all sorts of legal and illegal commercial activity. This, combined with economic scarcity, the remnants of the communist system, and the local criminal organizations it created, can be taken advantage of by foreign criminal groups. Together, these conditions could cause the deterioration of safety and security for the population. Identifying the risks associated with liberalization, and confronting them head on with workable solutions, could mitigate the negative consequences for ordinary Cuban citizens.

It is my unambiguous position that Cuba's economic liberalization and political democratization are desirable because a majority of citizens would benefit from them. However, all liberal transitions are fraught with peril, and these must be considered if a successful transition is to be accomplished.

How reforms are undertaken matters. Existing work on democratic transitions shows how order tends to diminish with a change of regime, which endogenously undermines a nation's chances of a successful transition to a more liberalized regime. There is also evidence showing how changes that liberalize economic institutions can disrupt the existing order. This book contributes to the discussion by pointing out these perils and other potential costs that could be minimized in order to increase the chances of a successful transition to a more functional economy and freer political system.

Despite my position on the need for a more democratic Cuba, I tried my best to approach Cuba without any preconceived notions on what is “positive” and what is “negative.” Instead, I base my arguments and conclusions on theories and evidence. Similarly, I do not argue for or against any particular subset of political actors that should bring change to Cuba's regime; which implies that I do not deem a change in rulers to be a necessary condition for improving Cubans’ economic and political conditions. Instead, I argue for a democratic change of the existing institutions. In this sense, the political survival of the current ruling coalition would be a function of its capacity to endorse and bring about institutional change.