By Mark Howell and C. S. Gilbert


President John Fitzgerald Kennedy in Key West

There are a number of Florida Keys connections to President John F. Kennedy and to the suppositions of conspiracies surrounding his assassination 50 years ago. Since the writers of this commemorative collection are Keys residents, those connections resonate. But above all the sightings, suspicions and speculations are the two times JFK actually visited Key West—the only sitting president, other of course than honorary Key Wester Harry Truman, who established his Little White House there, to do so.

The first Kennedy presidential visit was on Sunday, March 26, 1961, very soon after his January inauguration, to meet with British Prime Minister Harold Macmillan in a show of solidarity over a situation in Laos that could bring the world dangerously close to WW II.

As reported in the Key West Citizen, the initial meeting was almost jovial. “Glad to see you!” said Kennedy at Naval Air Station Key West on Boca Chica Key, extending his hand when the British prime minister, 24 years his senior, came down the steps of his British jet, which had flown to the Southernmost City from Trinidad.

“How long have you been waiting?” Macmillan asked as they shook hands.

Not long, Kennedy assured him. “We just got here.” In fact Kennedy had arrived only eight minutes earlier, at 10:46 a.m., in Air Force One, a black-nosed Boeing 707. He had flown from Palm Beach, his winter home; reportedly Palm Beach had in fact been the preferred site for the meeting. At the last minute, however, it was decided that an international conference at a major naval base such as Key West would send a stronger message to combat the aggressive threats of the U.S.S.R.

Kennedy and Macmillan met that day in 1961—in a time that almost seems nostalgic in 2013—as the “Big Two” of the western world. They sat down together in a second floor conference room at the Naval Administration Building, next door to Truman’s Little White House, in Truman Annex. With genuine cordiality, the two leaders came to an absolute agreement to call on Russia to accept a ceasefire in Laos, an embattled nation 8,000 miles from Key West whose fight against Communism, in retrospect particularly significantly, immediately preceded the United States’ involvement in Vietnam.

Cuba, too, was a point of universal concern. Entry to the meeting place involved driving eight miles from the Boca Chica runway to Old Town Key West, past Cuban anti-Communist demonstrators carrying signs reading, for example,  “Mr. President—Help Cuba, the Hungary of the Americas”—a reference to the eastern European nation invaded by the U.S.S.R. in 1956. Once in Truman Annex, the world leaders met in a conference room that had a view out over the Florida Straits directly toward Castro’s Soviet-supported island nation.

By 3:30 p.m., the meeting was over. (The luncheon menu was shrimp salad, sherbet and coffee at the Little White House.) As reported in the Citizen, Macmillan joked to Kennedy that if his plane, en route back to Port of Spain, Trinidad for the continuation of a Caribbean tour, were shot down, The U.S. would have an excuse to invade Cuba. In another aside to the meeting, Harold Evans, the British equivalent of Press Secretary Pierre Salinger, noted that he and the British newsmen (and in 1961 they were most certainly all men) accompanying Macmillan were “flabbergasted” by the informality of Kennedy during the lunch break, according to Bruce Rothwell of the London Daily Mail. Evans later reported that he was even more astonished to hear from Macmillan that the only thing keeping his headaches away was regular sex.  Another aside: Evans became editor of The London Times, then ironically became even better known as the husband of Tina Brown, the first British editor of The New Yorker.

JFK’s second visit to Key West took place Monday, Nov. 26, 1962 and was even more momentous than the first.  At 3:35 p.m. the President arrived at Boca Chica on Air Force One. This time he had flown to the naval air station from the Homestead Air Force Base, where the delegation picked up Rear Admiral R.Y. McElroy, host of the President’s two-hour visit of military facilities in Key West. Also on board were Florida Governor Farris Bryant, U.S. Representative Dante Fascell, plus all the fore-star admirals and generals in the Pentagon, including Adm. George Anderson, Gen. Curtis LeMay and Gen. Maxwell Taylor.

Among those greeting the august delegation on their arrival was Key West Mayor C.B. Harvey, who was widely quoted as saying that the nationally-publicized tour would do “a world of good” for Key West. His confidence could only have been strengthened by the arrival, on a second plane, of Salinger and 75 members of the White House press corps. The Navy ordered 30 extra typewriters to accommodate them. Local law enforcement was enlisted by the Secret Service to protect the President and his party; answering the call were Monroe County Sheriff John M. Spottswood, Key West Police Chief George G. Gomez and the Keys’ FBI agent, Ralph Jensen, plus Marvin W. Smoot of U.S. Navy Intelligence.

There appears to be no fly in the ointment of this meeting.Yet a mystery has appeared. A manifest of local officials invited to the naval air station to greet the President and his delegation remains in the historical archives of the Key West branch of the Monroe County Library. On that typed list is scribbled, in pencil, one additional name: Diosdada. Diosdada was at the time Key West’s only customs officer, identified in print as “a tough guy now (in 2003) retired in San Diego with alleged connections to the CIA.” He shows up in further investigation into the CIA’s alleged activities in the Keys.

In his Key West speech, Kennedy thanked the Navy, Air Force and Marine fliers whose reconnaissance flights over Cuba during the missile crisis “played the most important and the most critical part . . . in the most dangerous days that America has faced since the end of World War II.” He then toured anti-aircraft missile sites at the base. Then a motorcade of almost a dozen automobiles, led by a Lincoln Continental which had been borrowed from a Miami dealership bearing the President, traveled quickly from the air station to the Presidential Gates on Whitehead St., ceremonial entrance to NAS Key West, and on to the Little White House. En route on Duval St. the fast-moving motorcade was greeted by crowds of onlookers and flag-wavers. Yet the mood was reportedly somber.  Living only 90 miles from a potentially aggressive enemy can do that to a population.

At sunset, Kennedy and his party snapped to attention at the lowering of the colors. Then he was gone.

It was against this congenial background that Key West, with the rest of the nation and indeed the world, faced the inconceivable, shocking news of the assassination on Nov. 22, 1963 and the shooting on Nov. 24 of prime suspect Lee Harvey Oswald by mob enforcer and later FBI informant Jack Ruby. With Oswald, many believe, died the possibility of ever learning the truth about the assassination. But it is against that background the island city birthed a commendable tradition of investigative journalism, which led to the conspiracy theorist reporting that is alive and well in Key West today.

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