The end of Cuban exceptionalism has been much announced since 1989, but a decade and a half later state socialism on the island is still enduring. Transition studies have been criticized for focusing on success stories. Exploring the deviant case of Cuba’s “non-transition” from a comparative social science perspective can shed light on the peculiarities of this case and, more importantly, test the general assumptions underlying post-1989 expectations of regime change in Cuba. Theories of path dependence and cumulative causation are particularly helpful when attempting to link Cuban current political exceptionalism with a more long-term historic perspective. Moreover, they suggest that interpretations of Cuba as simply a “belated” case of “third wave” democratization may prove erroneous, even when the health of Fidel Castro finally falters.