Deep Cover / Shallow Graves: Stories and Flashbacks


The essays below include Tosh’s personal recollections of events he experienced over the nearly six decades after JFK’s assassination, as well as some from the six years prior to that going back to when he flew airplanes loaded with guns and ammunition into Cuba, in 1957. Over the last several decades, during his spare time, Tosh wrote about his personal recollections of the events he experienced as a pilot contracted by various government agencies. Many of these stories were based upon historic facts, while others reflected his “creative writing” skills as a budding novelist. These columns will present some of both genres.


Index of Articles

Page 1: Growing Up Fast: Two Events I Witnessed

Page 2: The Cubans and an Old Power Plant (1958)

Page 3: A Cold War Incident

Page 4: “A Mechanical Monster”

Page 5: The Day Before that Dreadful Day

Page 6: The Lady Saboteur

Page 7: The Gringo and the Worms

Page 8: The Death of a Reluctant Skydiver

Page 9: A Bogey Over the Florida Straits

Page 10: I’m Too Young to be Shot

Page 11: The Last of the Mohicans

Page 12: Two Good Friends: A War Story

To Go to Tosh’s Novel Page “Thinking That is Out of This World” Click HERE



Growing Up Fast: Two Events I Witnessed

Less Than 5 Years Apart

08 January, 1959: Fidel Castro’s Havana Cuba

One week after Castro’s triumphant 1959, New Year’s Day overthrow of Dictator Fulgencio Batista, who fled Cuba and went into exile in the Dominican Republic, I watched from a Havana side street, as  Castro and his rebel army marched into Havana Cuba. That was January 8, 1959.  I was twenty-one years old. I watched Castro ride proudly on top of an American Sherman tank that his rebel band of soldiers had captured earlier from Batista’s army. The massive Cuban crowd cheered, as Fidel passed. They shouted “Viva El Castro, Viva El Castro” — while others, in English, yelled “Long Live Fidel”.

I, too, was caught up in the hype of Castro’s July 26 Revolution.  I watched intently as the rebel leader approached the cheering crowd. Castro and his entourage, as they passed, waved and threw kisses and flowers to the cheering crowd of supporters.

Cuban Dictator Batista—after robbing the Cuban Treasury, filling his suitcases full of gold, Cuban pesos, and U.S. dollars—boarded a charter flight with his family, arranged by Miami organized crime and Havana casino operators and escaped to the Dominican Republic, into exile.

Fidel Arrives in Havana, Jan. 8, 1959

As Castro approached, I waved the fatigue hat that Fidel had given me when I was lost in the mountains of the Sierra Madre.  I waved it proudly as Fidel and his rag-tag army rebels passed by. That day was the beginning of deep dark secrets that I would carry with me for the rest of my life.

A few days after Castro entered Havana, Sergio, my Cuban friend, got me—undetected by Castro’s forces—safely back to the Sierra Madre mountains.

Eventually, we arrived at the coast, where a PBY seaplane, a Catalina, was waiting offshore. The PBY was registered to Texaco Petroleum and used as a ‘cut-out.’ for CIA’s secret Cuban operations.

Texaco leased the aircraft to Miami’s CIA Station to be used in the CIA’s covert Cuban Project.   The seaplane was based at Marathon Key, Florida. My Cuban friend, who I had flown with as copilot on other flights from Miami Station many times, Manuel Rojas, was the Texaco PBY pilot. He brought me safely from Cuba back to Marathon Key, Florida.

I was a young man in 1959—for the first eleven months I was just twenty-one years old—a copilot flying cargo to Havana in a C-46 airplane. The route was known as the ‘Rooster Hop’.  Rojas and I were on a retainer contract for CIA, (KUBARK) both working out of Miami Station, Miami, Florida. We were employed by Riddle Air Airlines of Miami.

When Castro rode into Havana on top of that American-made Sherman Tank, I was there to greet him. It was a real adventure for a young man barely twenty-one years old.  It was a dream come true for a young boy during World War II, who often dreamed of becoming a pilot.

The secret midnight charter flights from Miami to Havana and Havana back to Miami for the CIA in those days were an honor to fly.  I remember the difficulty of getting some U.S. government officials, and their Mafia counterparts, sobered up and off the island back to Miami, undetected.  Getting them safely back to the United States was, at times, a real challenge.

In those early days of the late-fifties, as a young man it was an honor to have been selected to be part of the new CIA and its Covert Action Group—and the CAG’s “Black Operations” (a.k.a. “off the books”).

22 November, 1963: Dallas Texas

However, for me, things would drastically change in the years to come.  In November of 1963, I was suddenly and without warning thrust into a very dark world. An unfamiliar world of which I had been kept unaware—through their “compartmentalization” system and the related “need to know” protocols. As I would eventually realize, it was an evil world of adventure and deception, a world of deadly state secrets.

The average eight to five hard-working American citizens could never begin to comprehend the existence of that crazy, sinister, evil, undercover world.

It was a cold windy November day in Dallas, Texas, when my world would change forever. That tragic November day in 1963 would haunt me for the rest of my life.

Why did I have to see that man die?”


Navigate To Other Tosh Articles . .

  • Page 2: The Cubans and an Old Power Plant (1958)
  • Page 3: A Cold War Incident
  • Page 4: “A Mechanical Monster”
  • Page 5: The Day Before that Dreadful Day
  • Page 6: The Lady Saboteur
  • Page 7: The Gringo and the Worms
  • Page 8: The Death of a Reluctant Skydiver
  • Page 9: A Bogey Over the Florida Straits
  • Page 10: I’m Too Young to be Shot
  • Page 11: The Last of the Mohicans
  • Page 12: Two Good Friends: A War Story

To Go to Tosh’s Novel Page “Thinking That is Out of This World” Click HERE

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