This is a NAVAL POSTGRADUATE SCHOOL MONTEREY CA report procured by the Pentagon and made available for public release. It has been reproduced in the best form available to the Pentagon. It is not spiral-bound, but rather assembled with Velobinding in a soft, white linen cover. The Storming Media report number is A397853. The abstract provided by the Pentagon follows: The tidal wave of democracy has yet to crash across the shores of Cuba primarily because the colossal personal of Fidel Castro has obstructed its path. What will happen when Castro is gone from the political scene? What forces, if any, exist on the Caribbean Island that would encourage change? Is the wave of democracy simply circling Cuba awaiting Castro's downfall or has Fidel created a breakwater that will keep his revolution alive well past his death? Castro's passing will undoubtedly bring about a leadership vacuum in Cuba that will thrust the island further along a transitional path, a path that began when Cuba lost its Soviet benefacton The purpose of this thesis is to explore the transition path Cuba has been on since the collapse of the Soviet Union in four key arenas: political society, economic society, civil society, and the international arena. It will also determine if these alterations have helped pave the way for liberalization and a transition to democracy after Castro is gone. In short, this thesis argues that what occurs in Cuba before Castro dies will determine what happens after he dies. Recommendations for U.S. policy are made based on the findin%s in this thesis.