HAVANA — When Fidel Castro rode victoriously into Havana on Jan. 8, 1959, Juan Montes Torre rushed into the streets to cheer. A poor, uneducated laborer from the eastern countryside of Cuba, he had arrived in the capital a few years earlier and, like most of his neighbors, could hardly believe what was happening.
“It was an emotional shock,” Mr. Montes said. “These bearded men, poorly dressed — they won! And on behalf of the lower classes!”
Mr. Montes, who was 25 at the time, stayed loyal to Mr. Castro, who died on Friday, from that moment. The Castro revolution gave him an education, a home, and a job as a police officer who sometimes guarded the comandante himself.
But that allegiance slipped from generation to generation in Mr. Montes’s family, and in Cuba as a whole. His son’s views darkened decades ago, during tussles with the Castro government’s restrictions. His teenage granddaughter, …