The rumor mill is abuzz in Washington with word that Ambassador Caroline Kennedy may represent the United States at the funeral of Fidel Castro on Dec. 4.
Speculation about the U.S. ambassador to Japan and daughter of President John F. Kennedy started almost immediately after the White House announced Monday that neither President Obama nor Vice President Biden will attend the official mourning ceremony for the late Cuban dictator.
Asked whether Kennedy was being considered and “what message would that send about America’s past and future relationship with Cuba,” White House press secretary Josh Earnest replied, “I can't even confirm that there will be [a delegation] at this point. But if there is one, we’ll certainly announce who will lead it and who will participate in it.”
There is powerful symbolism in John Kennedy’s daughter representing the U.S. at the funeral of the communist strongman. JFK authorized the unsuccessful Bay of Pigs operation against Castro as well as several assassination attempts.
But there may be another reason behind sending Caroline Kennedy to Castro’s funeral. One is the evidence that, toward the end of his life, President Kennedy was prepared to reverse his previous position and, in a second term, move toward rapprochement with the Cuban strongman.
In May, 1963, President Kennedy’s national security adviser, McGeorge Bundy, told him that measures being considered to topple Castro “will not result in his overthrow.” Although raids and sabotage continued against Soviet ships headed to Havana, Kennedy himself in the fall of 1963 told privately conceded to Soviet Ambassador Anatoly Dobrynin the raids were “serving no useful purpose.”
In late October of that year, the president gave an unusual interview to French journalist Jean Daniel, who was headed for Havana. In that interview, for the first time, JFK took responsibility for atrocities brought upon Cuba by Fulgencio Batista, the pro-U.S. strongman overthrown by Castro. As the President told Daniel, Battista was “the incarnation of a number of sins on the part of the United States.”
Kennedy asked Daniel to see him again after returning from Cuba and tell him Castro’s reaction, to his surprise, the dictator said he “would very much like to talk.” That was in November 1963, days before Kennedy was killed by an assassin’s bullet.
“The great likelihood that Castro was going to outlast U.S. plotting against him made it almost certain that Kennedy would have had to deal with him during that second term,” concluded Robert Dalek in his much-praised Kennedy biography “An Unfinished Life.” “And given the growing interest in moving beyond the stale conflict of the previous five years, who can doubt that a Cuban-American accommodation might have been an achievement of Kennedy’s second four years?”
“Fidel had a special place in his heart for the Kennedy family,” Peter Kornbluh, head of the left-wing Cuba Documentation Project, told Newsmax. “He welcomed John Jr., and RFK's sons over the years. Ethel Kennedy also. I sat with him and Jean Kennedy Smith at a state dinner in Havana in 2002. Caroline Kennedy would be extremely symbolic and appropriate.”
John Gizzi is chief political columnist and White House correspondent for Newsmax.
© 2026 Newsmax. All rights reserved.