After we had dinner in her New York apartment, Jacqueline Kennedy would open a bottle of Dom Pérignon and offer me a cigar from the supply she kept in an antique table drawer; a Por Larrañaga. Drawing on the cigar and drinking the Champagne, in which she invariably placed some ice, we would exchange reminiscences about the days we ran the world. One evening as she crushed out a cigarette and prepared to light another she asked me, "Why do you like those things?"

"Try it," I responded, handing her the lit cigar which she took, held gingerly between forefinger and thumb, and began to puff. "Don't inhale," I cautioned.

"They have a real taste," she remarked, handing it back to me.

"Well, that's why we like them," I responded.

It became an intermittent ritual. She would take a few puffs from my cigar, and then relinquish it to continue her chain smoking. I would estimate that over a period of years, starting during Lyndon Johnson's presidency, she consumed the equivalent of an entire cigar, making her the only former First Lady in this century to become a cigar smoker.

I never pointed out the obvious--that her cigars must have been illegally obtained. Not to spare her feelings, but my own, as it would have recalled one of the grimmest moments of my White House career. The Bay of Pigs had been bad enough, but even worse was that day in early 1961 when John Kennedy instructed me to draw up an executive order invoking the Trading with the Enemy Act against Castro's Cuba. It would mean an end to importation of Cuban products, including, calamitously, the cigars that had brought such pleasure to the numbing strains of Washington dinners. Before signing the order, Kennedy sent Pierre Salinger, and possibly others, to buy up a large proportion of the Cuban cigars still in Washington stores. Lacking the means for such a grand gesture, I had to be satisfied with a single box, which I rationed over a period of weeks.

At first the order did not prevent individual travelers from bringing in cigars, but protests from cigar makers in Miami--one of the first displays of political muscle by the now omnipotent Cuban refugees--closed this loophole. Still, for several weeks Kennedy continued to serve Cuban cigars at small White House dinners, until the possibility that they had been purchased prior to the embargo lost its credibility. However, staff and guests were the only sufferers, since Kennedy himself had a continuing supply imported in the diplomatic bag of his friend, British Ambassador David Ormsby Gore. It didn't seem fair. But as JFK would teach the nation, "Life is unfair."

Despite his own access, JFK's curiosity was aroused whenever a friend or guest produced a Havana. "Where did you get it?" he would ask, and listen delightedly as he heard another tale of human ingenuity in circumventing his own solemn presidential order. "It wasn't the cigar," a friend reported. "He loved the intrigue."

Like so many of his inclinations, JFK's cigar smoking emerged from the complex relationships of his multitudinous family--a story never told before this report. Prior to the Second World War, as the future president neared maturity, he often witnessed his father, Joseph Kennedy, finishing his meals by lighting up a cigar while lecturing his sons on the deficiencies of the New Deal and the poverty of a life devoted solely to making money. "I made the money so you could go into public life," he informed them while puffing contentedly on the finest Havanas. By the time the oldest son, Joseph P. Kennedy Jr., reached college--presumably eager to establish his own identity--he took up a pipe, and the mingled aroma of his aromatic blends and the Havana would settle with delicious ambiguity over the family. JFK, on the other hand, decided that he would prefer a good cigar. Like Dad. Thus was born the second most famous cigar smoker of the century, sprung, Athena-like, from sibling rivalry.

Although a true aficionado, JFK was never a dedicated smoker in the Churchillian sense, which may be why the small, slim panatelas that he favored were never renamed "Kennedys." He would usually puff one for a while, then set it down, unfinished and forgotten, while he became engrossed in conversation or in his dinner companion.

Cigars were an essential component in the glamour of the New Frontier and graced almost every Washington dinner party, where the men would light up after dinner while the ladies retired to another room. Nevertheless, it was in those primitive days of inherited sexism that I met my first woman cigar smoker. I was at a small dinner party to honor cellist Pablo Casals, the most renowned musician of his time, who was scheduled to perform at the White House the following evening. After the meal, I sat on the living room rug, smoking my cigar at the feet of the great man, when we were joined by the wife of future Supreme Court Justice Abe Fortas, who lit a Havana of her own while we listened to Casals discourse with vehement disapproval on the evils of composer Arnold Schoenberg and atonality. I regret that I was not then prescient enough to realize that Mrs. Fortas was not an anomaly or a curiosity but a pioneer of her sex.

The next night, following a formal dinner in the East Room of the White House, Casals played for the fortunate guests, the incredible sound of his cello echoing through the historic rooms that now are graced almost exclusively by country singers. Afterward, a select few were invited upstairs to the living quarters, waiting anxiously as the president settled into his rocking chair. An air of relief swiftly displaced anxiety as he drew a cigar from his pocket and lit it. It was the signal we had been waiting for. The president had begun. Now we could do the same. A dozen hands plunged into jacket pockets as we withdrew our own cigars, many of which were quickly replaced as a waiter passed among us with a box containing Romeo y Julietas. But Kennedy himself let the box go by, obviously preferring his own choice as we talked and puffed through the memorable evening.

Of course, all the cigar world now knows that JFK smoked cigars. Less well known, perhaps, is that Bobby Kennedy followed his brother in this, as in so many matters. And they always seemed to be of Cuban origin. Even as Operation Mongoose, under Bobby's direction, was plotting to "destabilize" Castro, the younger Kennedy was enjoying the most renowned product of the island. "What a family," I often thought, which had learned to preserve so determinedly amidst contradiction.

But a good cigar was sometimes more than a smoke. In the summer of 1961, a box of cigars served to herald a major diplomatic initiative by Cuba, one that became widely discussed only this year with the release of newly declassified documents.

In August 1961--a few months after the Bay of Pigs--the finance ministers of all the American nations gathered at Punta del Este, a seaside resort in Uruguay. The purpose of the meeting was to establish the Alliance for Progress, Kennedy's sweeping new policy for Latin America. Secretary of the Treasury Douglas Dillon headed the United States delegation and I represented the White House. Dillon was an impressive and distinguished figure as we entered the conference halls, but no one was looking at him. All eyes were on the youthful, bearded chief of the Cuban delegation, Comandante Che Guevara.

I never thought I might envy a communist, but there were moments, as I watched the young women following this fatigue-clad figure through the streets of the town, when I reflected how high the price of freedom might be. I, of course, was willing to pay it.

As I sat at the U.S. table in the conference hall, puffing a cigar of indeterminate origin, I was approached by a young Argentine diplomat whom I had met on a trip to Buenos Aires. "Che said he sees that Goodwin likes cigars," he said. "He bets you wouldn't dare smoke Cuban cigars."

"You tell him," I replied, "that I'd love to smoke Cuban cigars, but we can't get them." (Not completely true, as Cuba's security men were surreptitiously peddling cigars in the lobby of the hotel). That evening, two boxes of cigars were delivered to my hotel room. One box was for me. The other, more elaborate and inlaid with the Cuban seal, was intended for President Kennedy. It was accompanied by a note that said, in Spanish, "Since I have no greeting card, I have to write. Since to write to an enemy is difficult, I limit myself to extending my hand." It was signed "Che" over the typewritten "Comandante Ernesto Che Guevara."

The next day Che sent word that he would like to talk with me. A meeting was scheduled for the last day of the conference, only to be canceled by Dillon's order following an acrimonious exchange between him and Che. It is also possible that Dillon did not consider a presidential aide still in his twenties appropriate for such an encounter, although it was obvious that I had been chosen because Guevara wanted to talk with one of the "new Kennedy men," unencumbered by the rigidities and cautions of old-age diplomacy.

The conference ended, we drove to Montevideo where we would spend the night before returning to Washington on the plane Kennedy had provided. (Known as Air Force One when, and only when, the president was aboard). That evening, while eating dinner in the hotel, I was approached by two Latin friends who asked me if I would like to go to a party. The night was young, the plane would not leave until morning and my dinner companions were dull. I accepted without hesitation.

At a rambling, somewhat dreary apartment in a nearby residential section of the Uruguayan capital, about 30 people--I was the only American--were celebrating the birthday of a Brazilian official with an array of heavy pastries and rather dispirited samba music. As I talked with hopeful animation to a young Argentine woman in a tight-fitting flowered print dress--my choice of companion identifying me as a true Kennedy man--Che Guevara, wearing his combat fatigues, entered the room. He had, I later discovered, been telephoned by a fellow guest, a journalist in search of a story, and told where he could find me.

Uncertain, I debated whether to leave immediately and thus avoid a forbidden encounter, or remain and let events take their course. "I will not run out of a room just because a communist has decided to enter," I told myself, the patriotic bravado concealing my true reason for remaining: curiosity about this already legendary revolutionary and what he wanted of me. I was never to regret the decision, although, later, when a Senate committee investigated my encounter, I had some doubt of its wisdom.

After circulating for a few minutes, Guevara's eye caught mine and he approached, indicating that he wanted to talk. I told him I couldn't negotiate anything but would, of course, report what he said to "the right people." Gesturing toward the partygoers around us, Guevara motioned to the rear of the apartment where we could find some privacy. We walked to a small sitting room, accompanied by two young Latin diplomats, acquaintances of mine, who could interpret. I knew some Spanish, but not enough for this conversation.

At a distance the bearded Guevara had looked rugged, his bearing strong. But seated across from him in this small room, I saw that his features were soft, gentle, almost feminine, and he seemed uncertain, even anxious, as I waited for him to begin. "I would like to thank you for the Bay of Pigs," he said, his arms sweeping out in an expansive gesture as if motioning toward distant beaches. "Our control was incomplete. It rallied the people behind us, and allowed us to overcome the middle-class opposition."

What could I reply? It was all true. "You're welcome," I responded, adding, "Now maybe you'll invade Guantánamo."

The almost grim intensity of his expression was dissolved in a broad grin. "Never. We'd never be so foolish."

"Too bad," I said, then was silent waiting for him to begin. The conversation was not to end until dawn had lightened the Montevideo skies. He began by lecturing me on the inevitable failure of Kennedy's new Latin American policy, which called for large social reforms to accompany economic development. "It comes too late," he asserted. Having told me of America's difficulties, he then turned to his own, describing with dignified candor the economic difficulties of a Cuba cut off from its natural market and source of supply. In addition, since most of the production facilities had been imported from the United States, a supply of spare parts was essential to operation. Cuba badly needed a resumption of trade, he concluded, and perhaps, although admittedly this was doubtful, some inclusion in the new programs Kennedy had proposed.

What did I say? Very little. An occasional quip, a question or two. My position was already hazardous--for me--and any appearance of negotiation had to be avoided. We must not make the mistake, he told me, of thinking Castro was some kind of a moderate who had been transformed into a radical "by others." He was always a communist, but had concealed it to keep the United States from obstructing the Revolution. "Clever, even brilliant," I thought, for had we known what was coming, it is unlikely Castro would ever have reached Havana. But it did not seem wise, especially in the presence of two Latin diplomats, to state what we both knew to be true.

Still, he said, if we--Cuba and the United States--could reach, if not an "understanding," then a "modus vivendi," Cuba would pay for the expropriated properties. Cuba would also agree not to be involved in the export of revolution, he told me, speaking in guarded and general terms while looking toward the Latin diplomats whose governments Cuba was busily trying to subvert. And though his country's natural sympathies would be to the East, he informed me, gesturing vaguely toward a distant Soviet Union, it would establish no formal ties or alliances with any other power.

It wasn't a bad deal, if he meant it, and given what was to come later, a detached analyst might urge that it be pursued. But the mood in America was not one of detachment. The emotion that had always surrounded the "problem" of Cuba had, if anything, been heightened by our defeat at the Bay of Pigs. To make a deal with Castro, any kind of deal, would have been politically difficult, perhaps impossible. But we will never know, since Guevara's proposal was never pursued; at least not until the last days of the Kennedy Administration when the president, emboldened by his success in the missile crisis, began preliminary negotiations with Castro's Cuba, discussions abruptly terminated in Dallas.

As the sky lightened, I looked at my watch, realized our plane would leave in a couple of hours, and stood to leave. I extended my hand, but Guevara moved forward and embraced me--un abrazo. A communist, I thought, but a Latin American version, a blend the Russians would eventually find hard to deal with. I returned his gesture, my arms discovering an unexpectedly frail body.

I spent much of the flight home making notes of this encounter that I would later embody in a memorandum to the president, which after 35 years, was finally made public just a few weeks before I wrote this.

From Andrews Air Force Base, a helicopter took us to the White House lawn where Kennedy was waiting to welcome his delegation. After brief ceremonies, I walked with the president toward his office, telling him of my meeting with Guevara. Inside the Oval Office, I handed him the box containing the slim voluptuous cigars, which were not banded. "Are they good?" he asked.

"Good?" I replied. "Mr. President, they're the best."

Kennedy immediately took a cigar from the box, cut off the end, lit it and took a long, appreciative puff. Then he suddenly wheeled, pointing toward me, saying, "You should have smoked the first one."

"It's too late now, Mr. President," I rejoined, unaware that one of the plots to assassinate Castro had involved poisoned cigars. But perhaps he didn't know, either. Pointing toward the inlay on the box, he asked, "What's that?"

"It's the Cuban seal," I explained.

"Well, I can always keep the newspapers on top of it," he said, carefully placing the box on the table behind his desk.

In days to come he would allow me to take one of the cigars when I entered the Oval Office. (My own box was consumed rather swiftly.) A week or two later, I was emboldened to ask him for a cigar. "Your friends sent them, Dick," he said jokingly (I hoped), "take one." He opened the box, but it was now empty. He grimaced. Our disappointment was mutual. "Well," he said, "take the box. It's very nice, but I don't think the Cuban seal is exactly the right decoration for me." I took it, and have kept it ever since. It reminds me not only of those hope-charged years with Kennedy, but even more of Che, the romantic revolutionary who was killed while embarked on a doomed effort to lead a revolution in Bolivia. I was with Robert Kennedy when we learned of Che's death. It was not a happy moment. He might have been an "enemy," but he was a man of passionate belief who, in his own way, shared with us the conviction of the Sixties that entrenched power could be made to yield to human will and courage. And I liked him.

Richard Goodwin, who served in the Kennedy and Johnson administrations, is a writer living in Concord, Massachusetts.