Editor’s note: At about the time Fidel Castro relinquished the Cuban presidency to his brother Raúl in 2008, the late Ted Sorensen—advisor to President John F. Kennedy and the author of some his most famous speeches—wrote this reminiscence about Fidel to be held until the dictator’s passing. On Friday night, Cuban state television announced that the old revolutionary had died at the age of 90. Sorensen himself died in 2010, before the normalization of relations with Cuba had begun.

The death of Cuba’s Fidel Castro removes from the world stage a colorful, charismatic, controversial figure with whom I had three fascinating encounters over a period of 25 years.

In 1977, as an international lawyer in New York City, I was able to wangle an invitation to Havana during a temporary relaxation of the embargo during the Carter administration. On behalf of several clients who hoped to capitalize on possible trade deals (which were never struck), I had two meetings with Castro, both late at night. (I have never understood why dictators prefer to meet in their offices or homes well after midnight.)

Eight years later, in New York City to attend a special United Nations General Assembly commemorating the 40th anniversary of the UN founding, Castro addressed the Council on Foreign Relations, and we renewed our previous contacts in the receiving line of that distinguished organization, on whose board I served.

In October 2002, when American, Russian, and Cuban participants in 1962’s Cuban missile crisis organized another reunion in Havana under the auspices of Harvard and Brown universities (earlier “reunions” had been held in the U.S., Moscow, and Havana), Castro not only hosted the session in Havana—complete with a tour of the actual missile site—but hosted as well a luncheon for the principal members of the American delegation and a grand dinner dance for all attendees at which my wife, Gillian, and I were seated at his table.

At each of these occasions, I had an opportunity for (not surprisingly) lengthy exchanges with Castro, good-natured on both sides even when disagreeing on our perspectives and policy views. I found him full of humor as well as bombast, with a consistently good understanding of English and a keen interest in all things to do with America and John F. Kennedy, whom I had served as an aide.

During the second of my 1977 visits, I was having a luncheon discussion with the director of the Cuban Sports Authority about the possibility of a heavyweight match at Madison Square Garden (my client) between a leading American heavyweight and the Olympic champion from Cuba, when Castro suddenly walked in, seated himself at our table, and began amusing banter with the sports director regarding the rivalry in the intragovernmental basketball league competition between their respective offices. The director gently chided El Presidente for using, not always subtly, both his imposing height and his awesome title to intimidate the referee.

Whatever the differences in our views on politics and human rights, I found him to be an engaging, impressive, and intelligent figure in all of these encounters—even as, in both the 1977 and 2002 conversations, we offered starkly different views of how the missile crisis had unfolded and what it meant.

When, in our first 1977 meeting, I presented him with a copy of my first book, Kennedy, at the end of his opening monologue, he genially said, “I want to read this! Why didn’t you say so before?” I replied, “Because I could not get a word in.” In my toast at his 2002 luncheon, when I teased him for his bitter reference to Americans in the urgent Oct. 27, 1962, message he had sent to Soviet Chairman Nikita Khrushchev through the Soviet ambassador in Havana, urging Khrushchev to use the missiles to eradicate Americans, his command of English was sufficient to interrupt my toast: “This was only if you attacked!”

In hindsight, I told him, I was pleased he had sent that message, because it had alienated Khrushchev. Having been preceded by the shoot-down of an American U-2 reconnaissance aircraft overflying Cuba (a shoot-down Khrushchev had not authorized), Khrushchev saw the note as the “last straw” in persuading him that his entire “reckless gamble” in Cuba had failed and inducing him to withdraw the missiles on that final 13th day of the crisis. At that 2002 dinner dance, Castro was as jovial as he had been 25 years earlier, but appeared a bit less energetic; the ever-present Cuban cigar was no longer in his hand or mouth, and his speeches were shorter.

Illness was beginning to take its toll. Yet all these years, Fidel Castro has been the very epitome of a survivor. In his youth, the bearded guerrilla leader survived attempts by the Batista dictatorship to crush his revolution in the Sierra Madre mountains. Soon after assuming the presidency, he survived the attempt by a CIA-organized, trained, and equipped army of Cuban exiles to invade at the Bay of Pigs and (they foolishly believed) spark an uprising by any anti-Castro Cubans who were not by then already in prison or Miami.

Kennedy rued the day he permitted himself to be taken in by the false premises on which the CIA sold him that plan, and he grew over time to have a grudging admiration for Castro’s leadership skills (if not always his oratory). JFK and I were both present when a foreign-policy expert predicted with confidence that the “giants” of global diplomacy at that time—French President Charles de Gaulle, West German Chancellor Konrad Adenauer, Prime Minister of the United Kingdom Harold Macmillan, possibly even Chairman Mao, and Kennedy—would all be standing long after this Cuban upstart was gone. All of those giants were long gone before Castro’s death.

Castro survived the tanking Communist economy in Cuba, which he blamed on the U.S. economic embargo; he survived a variety of CIA plots to eliminate him as well as sabotage the island; he survived the dissolution of the Soviet Union, along with the trade and development assistance by which it sustained its cherished communist outpost in the Western Hemisphere; and he survived the Cuban missile crisis of 1962. Castro had little to do with the placement of the missiles on his island (and did not like that Khrushchev had done it secretly), and he had no say in their sudden withdrawal. Castro had wanted to condition their withdrawal on a series of American compromises that we would probably still be negotiating today if Khrushchev had agreed.

Not all revolutionary leaders successfully take on the burdens of the presidency (as Yasir Arafat demonstrated). But Castro survived a variety of domestic, political, and economic pressures and changes, continuing indefatigably on and on. (It almost seemed his motto was “Semper Fidel!”)

He was never a genuine threat to the national security of the United States, despite his failings on human rights and his early interventions in other Latin American and African countries. For years, the American economic embargo has had little reason or effect, except as a political sop to the older generation of Cuban-Americans in Miami who still hoped to return and take over the country. But it penalized American exporters, farmers, and tourists whose place was taken by our economic competitors from other countries in both hemispheres and by foreign travelers who enjoyed the splendor of Cuban beaches.

Today, with more thoughtful and flexible foreign-policy leadership in Washington—and a more realistic younger generation of Cuban-Americans in Miami—it will be interesting to see who and what emerge in Havana to replace Fidel Castro and his policies. The only certainty is that it would be absurd and counterproductive for the United States to dictate who should lead Cuba in the post-Castro era. In my 2002 visit, I had an opportunity to meet moderates and modernists in the Castro regime, which gave me hope that a new day will dawn in which diplomatic and economic ties will finally be normalized.

Castro’s distorted view of liberty matters very little now. The kingdom of heaven is by definition no democracy (assuming that is where he is). But he will feel right at home in continuing his way of making speeches that seem to his audience like they will last an eternity.