Bullet-riddled planes and a suitcase stuffed with cash

The escalating conflict between east and west following Russia’s invasion of Ukraine has reignited Cold War tensions. While Cayman may seem far removed from the threat of global conflict, the islands have borne witness, from close quarters, to some of the most dramatic moments in modern history. Few stand out more than the days in April, 61 years ago, when Cayman played an unwitting role in the CIA sponsored invasion of Fidel Castro’s fledgling socialist state in Cuba at the Bay of Pigs.

Chapter 1: A visitor in the night

The plane arrived in the night without lights, emerging from the darkness over the North Sound and landing on Grand Cayman’s unlit airfield in the hours before dawn.

It was a C-46 cargo plane belonging to Southern Air Transport, a carrier that would later become widely known as a front company for the CIA.

In April 1961, however, this was classified information.

Jack Rose, Cayman’s commissioner, a former RAF wing commander who served as a fighter pilot in the Battle of Britain, was only dimly aware of the aircraft’s mission and its origins.

There was no international telephone service from the Cayman Islands and Rose’s information was based largely on Morse code telegraphy from the governor’s office in Jamaica.

Via a cryptic, corrupted message – partially lost in transmission – he had been informed he would receive a visitor in the night and that this man, “should be given every courtesy”.

Only a few letters of the man’s name survived the shaky connection and the Commissioner felt he was “at a disadvantage” when the visitor stepped off the plane armed with a wealth of information about Rose’s life and career.

He littered the conversation with odd references to his university, his war record and his service in Northern Rhodesia.

The effect was disorienting and a little chilling, Rose acknowledged many years later in an interview for the Cayman Islands National Archive’s oral history project.

“He knew everything about me, and all I knew about him was about four or five letters of his name,” he said.

Mindful of his instructions, Rose offered the man a bed for what was left of the night, but the visitor was anxious to assess the situation on the ground in Grand Cayman.

Leaving his two suitcases with the commissioner, he and his crew immediately got to work.

It had already been a busy and intriguing day on the Caribbean island, at the time a sleepy community of 8,500 people. Things would get stranger before the episode was over.

Chapter 2: Bullet-riddled planes

Typically, no more than a handful of commercial carriers would take off and land from the rustic airstrip each day.

There was no fence around the complex at that time and approaching pilots had to do a ‘fly-past’ to ensure the runway was clear of stray cows before coming in to land.

Bob Hines, who manned the control tower, spotted the World War II era B-26 bomber circling the airfield around mid-morning.

The pilot’s voice crackled through the radio in heavily accented Spanish.

Hines couldn’t understand a word.

“Speak in English,” he instructed.

But the crew couldn’t make themselves understood.

In halting, broken Spanish, he attempted to communicate wind direction and runway position, guiding them nervously to a safe landing.

Two men in military fatigues jumped from the plane. One of them took out two weapons and handed them to the startled radio operator.

“Give you this,” he said, effectively surrendering to the one-man welcome party. His co-pilot did the same.

Hines made a call for reinforcements, initially summoning the chief of police, who also served as the island’s immigration officer.

As he waited, another plane – again, a B26 twin-engine bomber with a Spanish-speaking pilot and navigator on board – came in to land.

Over the next few hours, at least four planes of the same make and model touched down at the airstrip. Some were riddled with bullet holes. At least two of them still had rockets attached.

The arriving airmen, who appeared to be Cuban, willingly surrendered their arms and asked in faltering English to be transported to Miami.

Chapter 3: A surprising discovery

As the situation escalated, the crowd around the airport grew.

Billy Adam, who was 14 at the time, recalls cycling up to the airfield to investigate the commotion.

He had heard the roar of the bombers, passing overhead early that morning, and his interest was piqued.

When the aircraft began to land in Grand Cayman, word travelled fast through the ‘bush telephone’ and Adam, a curious boy with an interest in planes, was eager to investigate.

Memory fades with time and recollections differ on exactly how many planes landed and over what time period. Adam believes there may have been as many as six planes that touched down over the space of three days.

He remembers noticing that the planes outwardly displayed the markings of the FAR – Cuba’s Revolutionary Armed Forces – which had overthrown military dictator Fulgencio Batista in 1959.

On closer inspection, Adam says, he noticed the emblem of the US Air Force spray-painted over on the fuselage.

Again, recollections vary on how long the planes were left on the airfield. Hines, in his interview with the national archive, suggested it was a couple of weeks. Commissioner Rose indicated it was just a few days.

At some point during that period, Adam said he was able to climb aboard one of the aircraft.

“I walked through the bomb bay doors. It had been shot up so bad, it looked like a sieve,” he said.

“I went up in the cockpit and I saw the US Air Force insignia.”

Adam is well known in Cayman as a community activist, an advocate of transparency and a protester against perceived excesses of government.

The way he describes this episode is almost as if it were an origin story for a lifetime of scepticism.

He remembers asking himself why these American planes had been disguised as Cuban bombers. In the days that followed, he wondered why so many Americans suddenly appeared in Grand Cayman to work hurriedly on the stricken aircraft.

In the midst of all this, he listened with growing suspicion to radio news broadcasts of US President John F. Kennedy steadfastly denying any American involvement in the disastrous failed invasion of Cuba, supposedly led by exiled guerrillas opposed to Fidel Castro’s fledgling Communist regime.

“I was a little short pants boy and I could put two and two together,” he said.

“I told myself, ‘Billy, from here on, never believe anything government tells you until you can verify it for yourself’.”

Chapter 4: Bay of Pigs

Commissioner Jack Rose, armed with only marginally more information, found the situation equally odd.

The first he heard of any invasion of Cuba was over breakfast ‘one morning in April’ when a radio broadcast reported military activity in the Bay of Pigs area on the island’s south coast, around 200 miles to the north of Grand Cayman.

He was summoned to the airport around mid-morning and arrived to find what he described as an “American A-26 attack aircraft, in Cuban military markings”.

The plane, known both as A-26 and B-26 at different stages in its lifespan, was largely obsolete in the US at this point. Many had been sold as ‘excess’ after World War II and they were in common use in Latin America.

The Cubans’ request for passage to Miami struck him as odd. If they wanted to fly to Florida, why not do so themselves in their own aircraft?

Another strange detail stood out. Two of the planes had identical serial markings.

“Clearly there was something not quite right about these aircraft,” he recalled.

When he took the navigation maps from the cockpit, Rose discovered the planes had flown from Central America to the Bay of Pigs.

For the return flight an alternate course to Grand Cayman was marked out, ‘in case of trouble’.

Rose was miffed. You can almost hear traces of outrage returning in the transcript of his interview more than 30 years later.

“No one had bothered to mention to me that we might be expected to receive these unexpected visitors,” he explained.

“I was far from pleased to see them, as I smelt trouble.”

Rose was responsible for the island’s security and he had no advance warning of the issue.

After trading coded messages with Sir Kenneth Blackburne, the British governor in Jamaica, who had ultimate responsibility for the islands, he learned that he, too, was oblivious.

Was there someone higher up the chain who had authorised involving Grand Cayman in what later transpired to be a highly dubious, US-sponsored invasion of a foreign power, and kept everyone on the island, including its British-appointed leaders, out of the loop?

Had they put Cayman in the firing line in the escalating global Cold War between Russia and the US?

Would Fidel Castro, the firebrand leader of the Cuban revolution, consider the islands a co-conspirator with the US and a legitimate target for reprisal attacks?

These were troubling questions, not just for Rose, but for the CIA, whose supposedly secret role in the invasion was quickly becoming common knowledge. But on that morning, the commissioner had more pressing matters to attend to.

The planes were armed with a battery of rockets and machine guns, and laden with bombs that had not been discharged.

“When I checked the aircraft, the rockets and machine guns were still on ‘Fire’,” he said.

The Cubans were either ‘incapable’ or ‘disinclined’ to return to the planes to disarm them. 

So Rose enlisted the help of an American tourist, who had coincidentally crewed a US bomber in the 1950s, and removed the weaponry himself.

“It so happened that I had spent some time, during the 1939-45 war, flying rocket-firing Hurricanes and Typhoons, so that I was reasonably familiar with the unloading procedures,” Rose commented.

“A few Government employees gave a hand with the heavier bits, such as the bombs.”

Chapter 5:  Failed invasion

With the ammunition safely stashed away, Rose’s attention turned to the more fundamental question. What was going on?

As the afternoon wore on, an unofficial narrative began to take shape.

The planes that had landed on Grand Cayman were the remnants of an attempted invasion by American trained-and-organised forces, masquerading as a homegrown Cuban revolution against the Castro regime.

It later emerged that these were part of a brigade of exiled Cubans recruited by the CIA and trained in purpose-built facilities in Guatemala and Nicaragua.

The mission failed spectacularly, leaving 106 of the invading force dead, including four American aviators. The ground invasion saw 67 Cuban guerrillas killed by Castro’s forces. A further 10 were captured and killed by firing squad.

Ten Cuban airmen – part of the same anti-Castro brigade – were killed in action. The rest of the planes made it back to Nicaragua or diverted to Grand Cayman as the attack floundered in the face of resistance from Castro’s army and air force.

The episode damaged the US’ international reputation and emboldened the Soviet Union to align closely with Castro, leading directly to the Cuban missile crisis a year later – when the world stood on the brink of nuclear war.

An official CIA internal report of the events, declassified many years later, confirms that multiple planes made emergency landings on Grand Cayman because of a lack of fuel, or damage sustained during the invasion.

In the post-mortem of the failed invasion, questions were raised about the appetite of the Cuban recruits for the job at hand.

Rose, in his recollections after the fact, appeared unimpressed with the battle readiness of the crews that landed in Grand Cayman.

“The fact that they had landed on Grand Cayman, with most of their bombs, rockets and ammunition unspent, indicated clearly enough how little stomach they had for the job in hand,” he said.

On the afternoon of the invasion, however, Rose was operating largely in the dark and without the benefit of any instructions from the UK.

He arranged for the Cuban pilots and crews to be ‘fed and watered’ as he figured out what to do next.

Adam recalled that his parents, who both worked at the airport, took two of the group to the Grand View Hotel – now Margaritaville – for a ‘hearty Caymanian breakfast’.

Still unaware if the mission had been approved by the UK government, Rose tried desperately to keep a lid on the breaking story.

It was easier, in those days, to keep information from spreading beyond Grand Cayman. He summoned local boat captains with ship-to-shore radio and asked them to “refrain from mentioning our visitors” during their communications. He called the postmaster and had all outgoing mail stopped “until we knew what was what”.

This was “no doubt highly unorthodox, and possibly even illegal, but it seemed the sensible thing to do”, he said.

Chapter 6: A suitcase stuffed with cash

According to the CIA’s internal report on the Bay of Pigs invasion, the cargo plane, carrying the clean-up crew, arrived at 4am to recover the stricken aircraft.

Rose recalls it was closer to midnight.

Several men emerged from the aircraft – engineers and technicians who would spend the next few days working on the planes and readying them for flight.

The leader explained in vague terms what was going to happen. The Cuban pilots would be given civilian clothes and put on commercial flights back to Miami. The Americans would patch up the aircraft and be gone as soon as feasible.

He left his luggage with the commissioner and got on with the job of assessing the planes, before flying a 500-mile round trip to Jamaica to make a telephone call to update his superiors in Washington.

A few days later, according to Rose, all signs of the planes and their crews were gone. 

But the CIA visitor had left something behind.

“I later discovered that one of his two cases… one containing the usual essentials, change of shirt, underwear and so on, while the other contained money; stacks of dollar notes, neatly packed just as one sees them in films or on television as ransom money or the proceeds of a bank robbery,” Rose stated.

“This was to pay for anything deemed necessary; labour, fuel for the aircraft, food, overnight accommodation, or anything else and no questions asked.”

Chapter 7: ‘Approved in far-off places’

The question of what knowledge the UK government had, if any, before Grand Cayman was involved in such an audacious, covert military operation has still never been satisfactorily answered.

Rose said he was anxious about repercussions for some time afterwards.
He hints in his interview that he was told that Britain had approved the plan, keeping its own on-the-ground administrators in the dark.

“Eventually I learned through Sir Kenneth Blackburne that all was well, and apparently the measures taken had been approved in far-off places,” he said.

Some of this accords with the CIA narrative.

The Americans knew that flying from their base in Nicaragua to Cuba and back without refuelling was tight and the lack of a fall-back option was a cause for concern in the planning stages of the operation

“Grand Cayman Island was a much used emergency strip whose use, if not officially sanctioned, had the unofficial blessing of the British Government,” according to the CIA’s internal report.

Combined with the maps in the cockpit and Rose’s own account, the evidence suggests that the involvement of Grand Cayman was at least tacitly approved by the UK.

It was not lost on the CIA that this exposed the island to potential danger.

The prospect that Castro might respond aggressively to perceptions that Cayman was directly involved in the invasion, was considered a bargaining chip if there was any resistance to efforts to recover the B-26 planes. “It was suggested to *name redacted* that he might emphasise that unless the aircraft were removed, the possibility was that Cuba and other nations might believe that Grand Cayman was being used as the launch base in the effort against Castro,” the internal document indicates.

In the event, there was no such resistance, and it is not clear whether the veiled threat was ultimately considered necessary.

Rose, who died in 2009, believed the Cayman airstrip was intended as a last resort.

Even decades later, the former RAF commander, appeared annoyed that the Cuban guerrilla forces had not shown more stomach for the fight.

“Obviously, there was a diversion [planned] to Grand Cayman from there, in case they were in really serious trouble, but they weren’t in serious trouble at all, they just took the first opportunity of getting down on the ground,” he said in his interview for the national archive.

Chapter 8: ‘A microcosm of an ill-fated plot’

Despite that scathing assessment, there is evidence that at least some of the planes and pilots involved fought bravely against the odds.

Peter Kornbluh, the US National Security Archive’s Cuba specialist, believes that one of the planes that landed in Cayman was involved in the initial successful air-strikes on Havana.

Many of the shortcomings of the Cuban brigade, he says, were down to a lack of training and experience as opposed to an absence of courage.

Another factor was that the CIA spectacularly misjudged the amount of resistance the invasion would face. They had believed – and led their Cuban conscripts to believe – that Castro’s air force would be neutralised and the invading ground force would be greeted with open arms.

“The planes came to Cayman because they had been shot by ground fire and perhaps strafed by Cuba’s air force,” he said.

Kornbluh, who battled for years to have the CIA’s internal accounts of the Bay of Pigs debacle made public, said, “The Grand Cayman episodes are just a microcosm of the ill-fated nature of this whole, horrible episode.”

He believes the significance of the disastrous mission cannot be overstated. He said Castro had declared Cuba a ‘socialist state’ for the first time during a funeral for the men killed in the CIA-sponsored air strikes, setting up an alliance with the Soviet Union that spread instability throughout the region for years to come.

Epilogue: Cold War revisited?

While Cuba and Russia are much diminished powers since the collapse of the Soviet Union, the Bay of Pigs episode demonstrates how ‘the island that time forgot’ can be drawn, against its will and without its knowledge, into the midst of global conflict. Russian President Vladimir Putin’s invasion of Ukraine has reignited Cold War tensions.

Cuba is among a number of socialist or left leaning governments in Latin America that have offered vocal support to Russia, despite a global backlash and a raft of economic sanctions form the west.

Russia’s Deputy Foreign Minister Sergei Ryabkov was quoted earlier this year saying he cannot exclude dispatching “military infrastructure” to Venezuela or Cuba.

“I don’t want to confirm anything, I will not rule out anything… Depends on the actions of our American colleagues,” he said, in response to questions on Russian television.

The White House dismissed the comments as ‘bluster’.

Press secretary Jake Sullivan told the media, “If Russia were to move in that direction, we would deal with it decisively.”

The chances of that actually happening as Russian forces struggle to take Ukraine, appear remote.

A spokesperson for Cayman Islands Governor Martyn Roper said the current risk to the islands was considered “extremely low”. He declined to comment further.

• All comments from Jack Rose and Bob Hines in this story are sourced from transcripts of interviews recorded as part of the Cayman Islands National Archive’s Oral History Programme.