In the 1980s, most American foreign-policy experts and intelligence analysts failed to see the internal changes taking place in the Soviet bloc as serious challenges to the regimes. Could history be repeating itself closer to home, this time in Cuba?

After 50 years of living under the most repressive dictatorship in the Western Hemisphere, the Cuban people are losing their fear and beginning to push off the Communist boot from their collective neck. Paradoxically, this is happening as a dark cloud of authoritarian populism spreads throughout Latin America, financed by Hugo Chávez’s petrodollars, undergirded by Castro’s intelligence and security infrastructure, and …