Deep Cover / Shallow Graves: Unclassified Memories From an Old Declassified Pilot (PART 1)



The four essays below were previously posted separately, under their own titles. Combining Tosh’s short stories into sets of three or four articles allows us to efficiently present a “Reader’s Digest” version of his writings going forward. We hope to present new sets on a regular basis (bi-weekly or monthly) in the future, preserving his 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. Many of these will be based on historic fact, while others will reflect his “creative writing” skills as a budding novelist.


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?”


The Cubans and an old Power Plant—CUBA, 1958

Not far from the Cuban cane fields was an old abandoned runway. It was short and muddy—perhaps too short for our overloaded Twin Beech aircraft to take off. 

I sat in the cockpit, anxiously waiting for the penetration crews’ arrival, thinkingabout my situation: Here I am in this old, dilapidated airplane, deep inside Cuba, waiting for a bunch of idiot Cuban rebels to blow up a power plant that was never working in the first place, wondering if the engines on this old airplane will start. 

In the distance, I heard an explosion. That was the signal. The crew will be arriving shortly. I looked at the battered windsock near the end of the abandoned airfield. It pointed straight down, limp. There was no wind to help with the takeoff run. Yes, it was going to be a difficult takeoff, at best. 

I was a long way from Fort Bliss, Texas, and El Paso. How I got here, inside Cuba, I wasn’t sure. It just happened. There have been many weird happenings around me lately—strange things just popping up out of the clear blue—dangerous sinister people, strange faces, exotic places, and crazy love affairs. 

Yes, memories of Fort Bliss, Texas, were a long way back—Love Field airport and the one-horse town of Dallas, Texas, was even further. That early life in Northeast Texas was now a distant memory. CUBA? Well, that was another matter. Cuba was always in my thoughts and dreams.

The rumbling sound from the distant explosion disappeared, replaced with the chatter of small arms fire getting closer. I knew Batista’s army goons were chasing the penetration crew. We could have been wounded. I was one scared pilot. 

Sweating, hands shaking, I reached for the start button on the number one engine. The engine was running rough when we left Marathon Key. I wished I had never shut the engines down. I wasn’t sure they would start when I needed them. Shutting the engines down was a stupid mistake—perhaps, even a fatal error.

I thought about Christina, the Lady Saboteur. I wondered if she had cleared the power plant after the explosion and was running through the mountainous jungle trail, struggling through the cane fields, racing toward the aircraft. 

I forced the thought from my mind and pushed the start button on the number one engine. The engine cranked, but nothing happened. The prop just windmilled, going around and around. Round and round, the propeller turned. I moved the throttles forward, nothing. I adjusted the mixture and checked the boost pumps, nothing. The prop just kept turning, but the number one engine refused to start. Nothing seemed to work.

It was a hot, humid day. Nothing was going right. I could feel the cold breath of Batista’s firing squad on the back of my neck. I wondered what it would be like to stand before a Cuban firing squad. Would I stand tall, as I had seen in the movies? Or would I whimper and squirm like a blabbering coward. I saw myself as the blabbering coward.

I glanced out the cockpit window. The rebel demolition team was running along the jungle trail, dashing through the cane fields. They were running like hell, trying to reach the aircraft. I pushed the start button again. The starter was hot. I was frantic as the engine cranked, but the propeller was turning much slower. I was losing battery power. Worse yet, I was losing my mind. In panic mode, I pushed the button again. Then on the last turn of the propeller, the last ounce of battery juice, the engine kicked once, then kicked again—And then again. Thank God! – The engine slowly limped to life. Thick blue smoke rolled in billowing waves toward the rear of the aircraft. The number two engine sprang to life on the first crank. I was one happy pilot.

The power plant demolition crew, gasping for breath, jumped one by one on board—literally dragging and pulling each other into the aircraft. We were moving into the wind—what little wind there was—before cargo kicker Sickie Rick had closed and locked the doors.

We bounced down the crude, muddy, runway, slowly gaining takeoff speed. The number one engine was rough but turning positive power. That’s all we needed. All I had to do was get us off the ground and clear Cuban airspace; then, I could shut the rough engine down and ditch us in the ocean if we had to. However, if all went well, we would be out of Cuban airspace and back to Marathon Key by dark. 

My mind was absorbed with the task of flying the aircraft—and thinking of ‘The Lady Saboteur,’ but she was not onboard. I wondered where she was. I thought about her all the way back to Marathon Key. The non-operational power plant was totality destroyed, blown to hell.

When I returned to Miami, Frank Bender and Rex Beardsley, my two CIA case officers, debriefed the crew and me. During the debriefing, I learned to my dismay that the Cubans had blown up the wrong target. We would have to go back in with another crew tomorrow morning to demolish the right target, finish the mission, and save face with the Cuban underground. This time we knew Batista’s goons would be waiting.


A Cold War Incident

The six passengers, the team, were very quiet. They were not talking. The usual victorious chatter, jubilant cheers, and celebrations after a successful mission were missing.

I observed each one as I made my way to the cockpit. They appeared troubled, downcast, worried. It was written upon their ashen faces. I knew they were deep in thought. Perhaps each one asking themselves where they had failed? They witnessed the assassination they were sent to prevent.

I continued to the cockpit. Sergio, my Cuban friend, sitting in the shadows in the back of the aircraft, caught my eye. In shame, he quickly looked away. Gator, the quiet Cuban, sat alone staring at the cabin floor, nonchalantly sharping his switchblade knife. Gator always carried a knife secretly hidden inside his boot. As I passed by, he looked up, shook his knife at me, then mouthed the words “Fuck-It.”

Charlie, ‘The Blade’ turned his back on me, then spat on the cabin floor. Carlos, my friend since the days of MIAMI-JM/WAVE, said nothing. His dark, haunting Cuban eyes said it all. The other two passengers, heads bowed in stoned silence, shuffled their feet. They did not look at me as I passed.

All onboard the DC-3 aircraft, ‘Galloping Sue–Number Two’, knew the mission had failed. The President of the United States was dead.

Manuel Rojas stared out the cockpit window. He said nothing as I slipped into the right seat and buckled up. We sat quietly for a moment staring out our cockpit windows, still shaken by the tragic event we had witnessed earlier in downtown Dallas Texas, at Dealey Plaza. Neither of us spoke about the sad event.

I turned from the window, checked the cockpit instruments, and prepared for takeoff. In a daze and a confused state of mind, I fiddled around with my seatbelt. I raised the seat up and down a few times but finally left it the way it was.

Rojas was watching me; his steely dark Cuban eyes made me feel uncomfortable. My hands were clammy, sweaty. They shook slightly. I thought about what Sergio and I had witnessed earlier at the Plaza. In my mind’s eye, I could see it all again—a replay in slow motion. I fought back the image the best I could, but I soon started to cry openly. Rojas said nothing, but I could tell he was disappointed with me.

Sergio and I had also failed the Dallas mission. We had let a shooter from the south side of the Triple Underpass near the south parking lot escape. In our confusion and stupidity, we allowed the shooter to escape from the crime scene.

After what seemed like an eternity, Rojas suddenly turned from the window. He shouted to the crew in the back of the aircraft.

“Buckle up! Let’s get the hell out of here!”

I pulled the pre-flight checklist from the seat pouch and commenced to read aloud. Rojas harshly interrupted before I had finished.

“CLEAR ONE! He shouted.

Confused, I raised in my seat, glanced over his shoulder, attempting to check the prop of the left engine for clearance.

“ONE CLEAR!” Then added, “I guess.”

Rojas pushed the number one start button. The engine whined, turned three revolutions, kicked twice, and then started. Thick blue smoke billowed from the exhaust as the engine looped to life. Rojas adjusted the throttle on the number two engine.

“Two Clear.” He violently hit the start button. The number two engine sprang to life. In silence, we taxied to the runway.

The flight out of Dallas’s Red Bird airport was a sad event for everyone on board. The takeoff was routine. After clearing Dallas airspace, we flew north toward Wichita Falls, Texas. After a few minutes, we circled back toward Dallas, heading south toward Houston, Texas, flying VFR, Visual Flight Rules, no flight plan filed or required.

 We would refuel at Houston, Texas, on the Trans-Texas Airline side of Houston’s International Airport.  The Texas Air National Guard’s tarmac would provide our cover. We would head east after refueling, back to Miami, Florida, and Coral Gables, for our dreaded JM/WAVE debriefing with Frank Bender and Wild Bill Harvey.

After takeoff, I briefly looked back in the cabin, observing the passengers. Tears started to roll down my cheeks. Rojas looked at me in disgust, then shouted.

“Button it up, asshole, and quit your sniffling. There will be no crying or weakness on this flight.” Rojas paused and looked out the cockpit window.

“I’ve got to take a piss.”.

Rojas pointed toward the altimeter.

“Maintain three thousand and hold steady. You fly this damn plane, or I’ll find someone who can.”

He moved the throttles slightly forward, readjusting the power.

“You’ve got it! Now fly it. Hold this heading. Call me if you need me.”

He unbuckled his seat belt, got up, and quickly left the cockpit. He was gone, leaving me alone with my thoughts and an airplane to fly. My mind was a maze of cluttered images and ideas. I tried to piece together the events leading up to this day. I ask myself. Where and when, for me, did it all start? What were the events that led me into this dreadful November day?

Many decades have now passed, and I still wonder what would have happened if Sergio and I had prevented the assassin’s escape from that south parking lot? Would it have changed history?

For over fifty years, that thought continues to haunt me.


The Mechanical Monster

I could not escape the ominous sickening sound of the fierce battle echoing from the ravaged valley below. From the safety of the mountaintop, I watched as the machinery of war slowly crept forward.

In the distance, there was an explosion. I turned, watched giant fingers of fire escape from a burning building. The flames raced skyward, blotting out the sun. After the explosion and the curling black smoke had cleared, a ghostly figure, a lone soldier, staggered from the burning building. Leaving charred flesh and the carnage of war behind, the soldier inched himself forward, slowly escaping to a nearby field.

I watched mechanical iron monsters, with teeth of steel, like slithering snakes, slither into the valley. They ravished the countryside, destroying the landscape, annihilating cattle and men. I watched these mechanical monsters slowly moved forward.

Those monsters of iron and steel, I watched, charged across muddy fields, fording mighty rivers. I watched as they rapidly approached another village. Ruthlessly each monster crept onward, each one intent on eliminating a human life, and a way of life.

The lonely soldier, afraid and confused, finally escaped the smoke and flames. He staggered into a nearby muddy field where he knelt down upon the soggy ground. On his knees, he looked to the Heavens, then shouted out:

“Why! OH, WHY!”

He beat violently upon his chest.

“You Bastard. You filthy bastard! How could you let this happen? Why did you desert us in our hour of need? Have we not faithfully served you? Have we not given you our all? How could you do this to us?

From the smoldering burning buildings, another mechanical monster suddenly appeared. It crossed the muddy field and slowly consumed the kneeling soldier. Indifferently gorging itself on more burning buildings, devouring more soldiers and cattle, the slithering monster with teeth of steel continued its march onward, toward another unsuspecting village.

I watched the monster from the mountaintop. I watched it until I was sick. I watched until the sunset in the west; then I fell asleep. I never woke up.

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