On my Unusual Kentucky blog, I've delved into the curious connections between the JFK assassination and the city of Louisville; you may peruse those here and here if you wish to go down that rabbit hole. But as we'll see, there are plenty of Florida connections as well.
This blog post, like the aforementioned Kentucky ones, will assume you know the backstory to the general JFK assassination story and the characters who populate it. That being so, your mind may instantly assume that because of the role Cubans played in the drama, that Florida would be a natural spot for related conspiracy activity. And it appears your guess isn't far wrong.
At this link we find the texts of various declassified government files that a diligent seeker located on the National Archives database. One of them is ONI (Office of Naval Intelligence) casefile 173-10011-10157, which is in itself a relaying of an FBI report about "13 uniformed men seized in Florida, accused of planning attack on Cuba". I've done zero research on this so far, but am pretty sure this is one of David Ferrie's secret paramilitary camps where mercenaries were being trained for a planned invasion of Havana and ousting of Fidel Castro, all financed by Clay Shaw.
Another is a CIA document (104-10004-10235) in which a man named John K. Kaylock says he met Lee Harvey Oswald in Punta Gorda, Florida on October 2, 1963. And still another (179-40010-10186) is called "Jack Ruby in Florida". Ruby was always traveling around, ostensibly on business amongst the burlesque-club circuit (of which Florida is and was very well-represented) but of course he was working for a number of different people on a number of different projects with a number of different motives. The Mafia? The CIA? The Cubans? Probably all of the above.
Two different FBI reports exist investigating the relationship between Marina Oswald and her business manager - one James Martin - but interestingly, both reports came from the Tampa office. (Oswald and Martin both lived in Dallas and have no connection to Florida so far as I know.)
A 1967 FBI document (180-10020-10293) from a W.A. Brannigan to a W.C. Sullivan has the tantalizing subject header "JFK; CASTRO, FIDEL; DADE COUNTY, FLORIDA; OSWALD, LEE HARVEY".
Silvia Odio, a Cuban-American woman in Dallas, was paid a mysterious unexpected visit by two Cubans and a man calling himself "Leon Oswald". These men asked her to help them prepare a letter to solicit funds for an anti-Castro organization in which she was involved, the Cuban Revolutionary Junta (JURE). Odio testified that one of the Cubans identified himself by the "war name" of "Leopoldo" and that "Leon Oswald" was in the Marine Corps and was an excellent shot. She testified that the men told her that they had come from New Orleans and were about to leave on a trip for somewhere else. After seeing Lee Harvey Oswald's face on TV after the shooting of Kennedy, she realized he was "Leon." Silvia's brother Cesar was a city manager of Miami for eleven years, and she later moved to Florida herself. Her father was a Cuban refugee who was jailed for a failed assassination attempt on Castro in 1962.
Then there's this, which tells of a journalist's source claiming that Lee Harvey Oswald was in Florida to attend a speech given by Bobby Kennedy at Homestead Air Force Base in the summer of 1963. Oswald, in fact, was in Miami at the time, but doing what exactly is uncertain. There are FBI dox (180-10029-10313) from the Dallas office to the Miami office, in fact, about Oswald's activity in Florida. Considerable efforts were made by agents to learn more about Oswald's involvement with the Tampa chapter of the Fair Play For Cuba Committee but nothing conclusive was learned.
Most interesting of all to me, however, is the strange case of Kerry Wendell Thornley.
In 1959, Thornley was in the Marine Corps, and served in the same radar unit as Lee Harvey Oswald. They had a sort of combative friendship, often arguing about politics, and philosophy, and discussing books like George Orwell's 1984. After the two were reassigned to different units, Thornley learned of Oswald's autumn 1959 defection to Russia in the Stars and Stripes military newspaper.
In February 1962, Thornley wrote a book called The Idle Warriors about his experiences with Oswald. Because of this, he was called to testify before the Warren Commission in 1964. After he'd moved to Tampa, he was hounded by Jim Garrison, who was convinced of Thornley's complicity in the conspiracy. Thornley's physical resemblance to Oswald caused some speculation that he was one of the "fake Oswald" doubles that were going around. These accusations were eventually dropped by Garrison's successor.
Thornley, who spent two years living in New Orleans, encountered a creepy pair who called themselves Gary Kirstein and Slim Brooks, who claimed to have inside info on various matters conspiratorial. He later became convinced these men were Howard Hunt and Jerry Milton Brooks, and believed that Oswald had been a deep-cover agent involved with MK-ULTRA. Anecdotes about the revelations of Kirstein and Brooks filled his writings for the remainder of his life, and he published handmade zines from a garage in Atlanta for the rest of his days.
As an impressionable lad and avid reader of his works, visiting Thornley was top of my to-do list when I moved to Atlanta in 1984. Though Thornley was well-known for his paranoia, he openly used his actual street address on his zines, not a post office box. I found the street, a cul-de-sac called Lookout Place, on a map and went there to say hello. But a young man answered the door when I knocked, and said Thornley actually didn't live in the house, he lived in the garage. "He's probably sleeping right now," he said, "but you can try him."
I knocked on the garage door, and the man himself emerged. Though he was groggy from being awakened, he immediately remembered me from mail correspondence, and we chatted a few minutes; mostly about a theory he had about a conspiracy of clowns - like, actual circus clowns - driving cross-country abducting hitchhikers. He loaded me up with back issues of all his zines and broadsides I'd missed, and made some rumblings about needing to get back to work. I thanked him for his time and excused myself, wondering if I'd just had a brush with greatness or a meeting with a madman. Both, maybe?
(And though I was a fan of Robert Anton Wilson's Illuminatus! trilogy and the Discordians, at that point I had no idea that Thornley was actually the founder of the Discordians, under the pen name "Omar Khayyam Ravenhurst" - something I didn't learn until many years later.)