LAST WEEKEND, Senate minority leader Tom Daschle spent seven hours talking to Fidel Castro in Havana. U.S. Chamber of Commerce president Thomas Donohue spent three days there last month. In June, low-level State Department and Coast Guard officials met with their Cuban counterparts to discuss the potential for collaboration on drug interdiction operations. More and more officials, it seems, are pursuing a dialogue with Castro's government.

But not the White House. Fearful of a right-wing attack at the first sign that Washington might engage in diplomatic discussions over its long-standing differences with Castro, the Clinton administration has rejected all high-level talks with the Cuban government.

A diplomatic dialogue with Cuba should not be considered heresy. Every president since John F. Kennedy has attempted -- in secret -- to discuss U.S.-Cuban relations with Castro. Indeed, according to recently declassified documents, Kennedy was seeking to negotiate a rapprochement before he was assassinated in Dallas. The details of this long-hidden history carry immediate relevance to current policy toward Cuba.

John F. Kennedy would seem the most unlikely of presidents to seek an accommodation with Fidel Castro. His tragically abbreviated administration bore responsibility for some of the most assertive U.S. efforts to roll back the Cuban revolution: the Bay of Pigs invasion, the trade embargo, Operation Mongoose and a series of CIA-Mafia assassination attempts against the Cuban leader.

Unknown to all but Robert Kennedy and a handful of advisers, John Kennedy began pursuing an alternative tact on Cuba in 1963: a secret dialogue toward a rapprochement with Castro. To a policy built upon "overt and covert nastiness," as Top Secret White House memorandums characterized U.S. operations against Cuba, was added "the sweet approach," meaning the possibility of "quietly enticing Castro over to us."

In a memorandum on "The Cuban Problem," Kennedy's National Security Adviser, McGeorge Bundy, provided the rationale for this type of initiative:

"There is always the possibility that Castro or others currently high in the regime might find advantage in a gradual shift away from their present level of dependence on Moscow. In strictly economic terms, both the United States and Cuba have much to gain from re-establishment of relations. A Titoist Castro is not inconceivable and a full diplomatic revolution would not be the most extraordinary event in the 20th century."

For the Kennedy White House, there was nothing incongruous about such a policy turnaround, Bundy explained in an interview shortly before his death. "We wanted to make a reality check on what could or could not be done with Castro," he said. President Kennedy, according to Bundy, "clearly thought this was an exploration worth making because it might lead to something." Kennedy was "strong enough to explore it in a politically non-dangerous way."

Ironically, the opportunity to communicate covertly with Castro arose from the two most hostile episodes in U.S.-Cuban relations: the CIA-directed invasion of the Bay of Pigs, and the missile crisis. Negotiations for the ransomed return of 1,200 Bay of Pigs prisoners provided the contacts and confidences under which the first messages could be passed; and the Kremlin's unilateral decision to withdraw its nuclear missiles appeared to provoke a Cuban-Soviet breach that the U.S. could exploit.

The first private channel to Castro was James Donovan, a Washington lawyer negotiating the release of the Bay of Pigs prisoners. During the late fall of 1962, Donovan became the first American emissary to gain Castro's ear and his trust. Secretly representing the Kennedy brothers, Donovan arranged a trade of $62 million in food and medicines for the imprisoned brigade members. During the spring of 1963, he continued his trips to Havana to secure the release of two dozen American citizens, including three CIA operatives, held in Cuban jails. Debriefed by U.S. intelligence officials after each trip, Donovan described his meetings with Castro as "most cordial and intimate."

In late January 1963, as he was boarding his plane to return to the United States, Donovan reported, Castro's aide de camp, Rene Vallejo, "broached the subject of re-establishing diplomatic relations with the U.S."

During Donovan's visit in March, Castro raised the issue, asking how, given the political climates in both countries, talks could be initiated. "So I said to him, 'Do you know how porcupines make love?' and he said, 'No'," Donovan later told the CIA. "And I said, ... 'Very carefully. And that's how you and the U.S. would have to get into this.' "

That month, a State Department official suggested that Donovan be instructed to tell Castro that "breaking Cuban relations with the Sino-Soviet bloc" was a non-negotiable U.S. demand for improved relations. But Kennedy overruled the official. "The President does not agree that we should make the breaking of Sino/Soviet ties a non-negotiable point," stated a Top Secret/Eyes Only memorandum recording Kennedy's instructions to Bundy. "We don't want to present Castro with a condition that he obviously cannot fulfill. We should start thinking along more flexible lines."

Kennedy's position "must be kept close to the vest," the memo advised. "The President, himself, is very interested in this one."

The first bilateral talks between top U.S. and Cuban officials took place amid cocktails, finger foods and several dozen members of New York's high society, at the apartment of ABC News reporter Lisa Howard. Howard, who had done a television special on Castro in April 1963, offered herself as an intermediary in the secret dialogue and her home as a communications center.

On Sept. 23, Howard invited Cuba's United Nations Ambassador, Carlos Lechuga, and William Attwood, deputy U.S. ambassador to the U.N., to a reception where they could talk unnoticed. Standing in a corner of Howard's spacious living room, Attwood and Lechuga conferred on the interest of their respective leaders in what Attwood called "an exchange of views."

Castro, Lechuga told Attwood, "had hoped to contact or get in touch with President Kennedy in '61 and then came the Bay of Pigs and that was that." Lechuga "hinted that Castro was indeed in the mood to talk," Attwood reported in a secret account of his meetings, and "thought there was a good chance I might be invited to Cuba if I wished to talk to Castro."

Throughout the fall, a series of telephone calls, messages and communications took place in Washington, at the U.N. and in Howard's apartment:

* On Sept. 24, Attorney General Robert Kennedy told Attwood that "it might be possible to meet Castro," but not in Cuba. He suggested Mexico or the United Nations.

* On Oct. 29, Castro aide Vallejo called Howard and said the Cuban leader could not leave Havana at this time but "would send a plane to Mexico to pick up [Attwood] and fly him to Veradero for a private talk." Howard suggested that Vallejo come to the U.N. "as Castro's personal spokesman."

* On Nov. 5, the White House considered the proposal. Bundy told Attwood that "the president was more in favor of pushing towards an opening toward Cuba than was the State Department, the idea being -- well, getting them out of the Soviet fold and perhaps wiping out the Bay of Pigs and maybe getting back to normal."

* On Nov. 11, Vallejo again called Howard to say that Castro would be willing to send a plane to Key West, Fla., to secretly pick up the U.S. emissary.

* On Nov. 19, Attwood spoke to Vallejo at Howard's apartment, telling him that the U.S. preferred a preliminary secret meeting at the United Nations to discuss "an agenda" for talks with Castro.

"The President decided that it might be useful for me to go down to Cuba and see Castro," Attwood recalled in an oral-history interview, "but first we'd have to know what the agenda was."

After the agenda was received from Cuba, Attwood was told by White House officials, "the president wanted to see me at the White House and decide what to say and whether to go [to Cuba] or what we should do next." As Attwood later testified, "that was the 19th of November, three days before the assassination."

In the 72 hours before his death, Kennedy sent two messages to Castro. In a speech before the Inter-American Press Association in Miami on Nov. 19, he stated that Cuba had become "a weapon in an effort dictated by external powers to subvert the other American republics," Kennedy stated. "This and this alone divides us. As long as this is true, nothing is possible. Without it, everything is possible."

According to White House aide Arthur Schlesinger, who helped write the speech, Kennedy's language was intended to convey to Castro the real potential for normalization between the two countries.

Kennedy's second message of interest in a detente was delivered to Castro by French journalist Jean Daniel on November 20 and 22. "I interpreted Daniel's visit as a gesture to try to establish communication, a bridge, a contact," the Cuban leader would recall. Before learning of the assassination, Castro told Daniel that Kennedy could become "the greatest president of the United States, the leader who may at last understand that there can be coexistence between capitalists and socialists, even in the Americas."

When an aide interrupted the conversation to report that Kennedy had been fatally shot, Castro turned to Daniel and said, "This is an end to your mission of peace. Everything is changed."

Little has changed in U.S. policy toward Cuba during the past four decades. For that reason, this history remains important to considerations of the present. As the Clinton administration ponders the politics of dealing directly with Castro, it should consider the meaning of the aborted Kennedy-Castro initiative toward a rapprochement. At the apex of the Cold War, high-ranking members of the Kennedy White House, including the president, thought a dialogue toward coexistence was possible and indeed preferable -- in a world far more dangerous than today's.

Years after the Kennedy episode, William Attwood returned one more time to his role as an intermediary in U.S.-Cuban relations. After Jimmy Carter's election, Castro invited Attwood and his family to visit Cuba. When he got back from the trip, Attwood wrote a comprehensive confidential report for Secretary of State Cyrus Vance.

Diplomatic relations are "up to us," according to Attwood's memorandum of his conversation with Castro. "If we want to be friends, they'll be friends. If we want to continue being their enemy, they'll be our enemy. They've grown used to it."

Peter Kornbluh is a senior analyst with the National Security Archive, a public interest research library. This article is adapted from a longer version that appears in the current issue of Cigar Aficionado.

"The president does not agree that we should make the breaking of Sino/Soviet ties a non-negotiable point. We don't want to present Castro with a condition that he obviously cannot fulfill. We should start thinking along more flexible lines."--- From a secret 1963 memo

Fidel Castro said Kennedy could become "the greatest president of the United States, the leader who may at last understand that there can be coexistence between capitalists and socialists, even in the Americas." --- Speaking to French journalist, 1963