If these were ordinary times, I might argue that the death of Fidel Castro, the revolutionary who brought the world to the brink of nuclear annihilation, the dictator who outlasted 10 U.S. presidents and nearly outlasted an 11th, marks the symbolic end not only of the Cold War but of the 20th century itself.

But these are not ordinary times, and I suspect that El Commandante, if he was in command of any of his faculties in his final months, was watching the machinations and manipulations of Vladimir Putin, the ex-KGB man and current dictator of Russia, with some wonder, and more than a little envy.

This is because Fidel, unlike his brother, Raul, who took power when Fidel fell ill in 2008, did not find the new dispensation at all amusing. This new dispensation was one created largely by President Obama, who decided that the decades-old American taboo against normalizing relations with Cuba was retrograde and futile, and so violated it, with alacrity, and with at least provisional success.

The decision to restore diplomatic relations with the Communist regime in Havana was met with relief across much of Latin America; with happiness in many quarters in Cuba; with anger among a surprisingly modest number of Cuban exiles in the U.S; and with chagrin in the modest, rigorously guarded Boca-Raton-style bungalow Fidel Castro had made into his retirement home.

Fidel reveled in his half-century confrontation with America, and, he knew, I believed, that it would be more difficult for Cuba to resist battalions of Yankee capitalist hoteliers and an invasion fleet of Fort Lauderdale-based cruise ships than it was to defeat the hapless landing party at the Bay of Pigs.

A couple years ago, on a road trip to the colonial city of Trinidad from Havana, I took my family on a detour to Playa Giron, the beach on the Bay of Pigs where the American-led invasion ended in catastrophe for the CIA and for the Cuban exiles it trained. Near the beach was a beat-up shop that sold, like most stores in Cuba, very little. This one stocked mainly Che Guevara T-shirts, and, oddly enough, Pringles and Coke. One of my daughters saw the stacks and stacks of Pringles and drew the appropriate conclusion about the inevitability of American capitalism. “Look,” she said, “we won.”

On my first visit to Cuba, in 2010,  I spent a phantasmagorically strange week with Fidel, and in our meetings I heard him suggest in various ways that he knew what was coming. At my first lunch with him—a lunch at which the allegedly ailing Fidel drank wine and spoke extemporaneously for hours—his prolixity did not surprise me, but his self-awareness, and humor, sometimes did. When I asked him if his illness and advanced age had caused him to rethink his position on the existence of God, he answered, drily,“Sorry, I’m still a dialectical materialist.” At another point, he showed us a series of recent photographs taken of him, one of which portrayed him with a fierce expression. “This was how my face looked when I was angry with Khruschev,” he said. The reason he was angry at Khruschev would soon come up in our conversation.

His self-awareness evinced itself most notably during a discussion about the relevance of Cuban revolutionary socialism. I had asked him if he believed that the Cuban model was still something worth exporting. He answered, “The Cuban model doesn't even work for us anymore.” As I wrote at the time, this struck me as the mother of all Emily Litella moments—it seemed as if the leader of the Revolution had just said, in essence, “never mind.”

I was traveling on this trip to Havana with Julia Sweig, one of America’s leading experts on Cuba, and especially the Castro brothers, and I asked her after lunch what he could have possibly meant. “He wasn't rejecting the ideas of the Revolution,” she said. “I took it to be an acknowledgment that under ‘the Cuban model’ the state has much too big a role in the economic life of the country.”

Julia and I spent most of that day, and part of the next, talking with Fidel not about Cuba’s constantly collapsing economy, but about the threat of nuclear war. He had called me down to Cuba—his representatives summoned me for an audience  three days before they hoped to grant me this audience—to discuss my writing on the Iranian nuclear threat, and the possibility that Israel or the U.S. would use military force to stop Iran from crossing the nuclear threshold. The ironies here were great—Fidel had read my articles on The Atlantic’s website, which few of his subjects could do, because he had made sure that the internet was more-or-less verboten in his one-party dictatorship. Another irony—or at least, absurdity—was that Fidel was trying, in these conversations, to make a point about the dangers of nuclear war. This was somewhat rich, considering the particulars of his role in the 1962 Cuban missile crisis. This is from my original report on this portion of our rolling conversation. I had asked him if his fear of nuclear war in the Middle East was informed by his earlier experiences:

I mentioned to Castro the letter he wrote to Khruschev, the Soviet premier, at the height of the crisis, in which he recommended that the Soviets consider launching a nuclear strike against the U.S. if the Americans attack Cuba. "That would be the time to think about liquidating such a danger forever through a legal right of self-defense," Castro wrote at the time.

I asked him, “At a certain point it seemed logical for you to recommend that the Soviets bomb the U.S. Does what you recommended still seem logical now?” He answered: “After I’ve seen what I’ve seen, and knowing what I know now, it wasn’t worth it all.”

Though he had apparently reached the conclusion that the nuclear destruction of the United States would not have been a good thing, his resentment of the U.S. was still ferocious, even in old age. At the end of our long lunch, Fidel announced that we would all be attending a dolphin show at the Havana aquarium the next day. (This is when I began to understand the true nature of dictatorial power: When his son, Antonio, informed Fidel that the aquarium was actually closed the next day, Fidel lifted a finger and said, like a pharaoh, “It will be open tomorrow.” And it was.)

You can read about this exceedingly odd visit to the Havana aquarium here (Che Guevara’s daughter, a dolphin veterinarian, makes a guest appearance). But there was one moment, one strange moment among many, that I didn’t mention then, but seems particularly relevant now, in the new age of Cuba-U.S. relations. At a certain point, Fidel, who loved the aquarium, told me, “Our dolphins are better than the American dolphins.” I laughed, of course, and noted that Cuban dolphins and American dolphins are the same dolphins; Cuba and Florida are only 90 miles apart. But he meant the dolphins in the custody of the state aquarium. “We do not exploit our dolphins for profit,” he said, adding that Cuba takes better care of its dolphins than does the cruel, aquatic-mammal-exploiting, Cuba-invading imperialists to the north.  

He was trying to make a larger point, of course. Fidel’s competition with the U.S. knew no limits. For all I know, he may have been right about the dolphins. But the point that he has tried to make for more than half-a-century—that the Cuban people are in better shape than the American people—always struck me as a reach. Assessed a certain way, Cuba’s achievements in health, in particular, can look impressive. But his state never stopped oppressing its own people. It still does, under his brother’s rule. But the Cuban model will not last forever, and this is what Fidel, in his final years, worried about the most.