Cubans are great believers in anniversaries and never more so than since 1959.1 The purpose of this is clear. They provide occasions for sustaining the revolution’s momentum and reviving waning enthusiasms - no easy matter given 30 years of inhibiting and unremitting blockade and consumer shortages. There is no particular magic in celebrating the thirtieth anniversary: the twenty-sixth year would have had more resonance, at least for Fidel Castro. But there is a serious case to use the occasion for a reassessment of where the revolution has come from and where it is going. It has certainly not reached the end of the road but it has come to a crossroads. Short-term developments and long-term global events have converged to give urgency to such a reassessment. This article is a modest attempt to put the revolution in a broad comparative perspective by discussing some of the specific aspects of the trajectory of Cuba’s history without which it is difficult to appreciate the revolution’s uniqueness and to identify some of those factors that will have to be taken into account in the construction of future scenarios.