When three CIA agents bungle their way into Fidel Castro’s clutches on the eve of the most dangerous international standoff of the 20th century, they are sentenced to Cuba’s most notorious prison, the Isle of Pines. Escape seems impossible. This is the previously classified story of a Hail Mary plan, a Dirty Dozen crew of lowlifes, and a woman who wouldn’t bow to authority as she fought to bring them home.

Greg Nichols
Jul 9 · 41 min read

The interrogators were doing a lousy job. Never mind that David Christ was the one being interrogated. It was his professional opinion that these Cubans couldn’t make a can of beer sweat.

Listen to the audio version of this story from Audm.

It was the middle of the night but hot as an oven in Havana. Christ had just been dragged from his cell in the bowels of G2, the Cuban intelligence agency, to a small interrogation room that held one desk, two chairs, and three Cubans. In Christ’s view, they were a motley crew of lowlifes — which made it all the more humiliating that they’d caught him red handed. One of the Cubans wore baggy slacks and a Hawaiian shirt. He looked like a pimp. The second was big as a refrigerator. He barely moved, just flexed his biceps and glared from a damp corner. The third ran the show. He had a chubby face and bad teeth riddled with festering holes. Christ nicknamed him bad teeth.

“What are you doing here?” Bad Teeth asked in English.

“Tourism,” Christ answered.

“Why are you here?”

“To see your fine country.”

“You work for the CIA, don’t you?”

“No, I don’t work for them.”

Bad Teeth’s English was quite good — a far sight better than Christ’s Spanish. He was smart, Christ could tell, which made him dangerous. The others just stood and gawked. In lieu of words, The Pimp played with his gun, spinning it around his finger like a five-year-old mimicking a gunslinger. That made Christ nervous. G2 agents had a way of shooting themselves by mistake — and if not themselves, someone else. It had already happened once. Shortly after Christ and the others were detained, one of the crackerjack Cuban agents shot himself in the hand while fiddling with his gun. Normally that would have struck Christ as amusing, a revolutionary blowing his thumb off. But under the circumstances …

“Why are you here?” Bad Teeth set in again.

Christ couldn’t believe it. He was a senior CIA officer in charge of one of the most specialized units in the Agency doing his damnedest to sound like a tourist in the wrong place at the wrong time.

How was he going to get out of this one?

John Mertz had a handful of options, and he hated all of them.

News that three Agency men had been captured on assignment in Cuba was about as welcome as an envelope full of fish guts. That one of the men was David Christ, a CIA higherup with lots of secrets and no business being in the field? Well, that was an atom bomb, the kind of fuck-up that prompted a lot of conference room doors to slam urgently around Langley. Mertz got the call from the very top: It was up to him to get the captured agents back.

The whole Cuban situation was spiraling toward disaster. Communism had arrived in the Caribbean on New Year’s Day, 1959, when Fidel Castro and his band of pirate-revolutionaries ousted the country’s American-backed president, Fulgencio Batista. Diplomatic relations still stood between the U.S. and Cuba by the fall of 1960, but only just. The man with the fat cigar was rounding up counter-revolutionaries and political prisoners by the busload, lining them up against tropical-colored walls to be shot. American businessmen and rich mobsters crammed dirty cells in Havana.

Eisenhower was on his way out, and a nail-biter of an election between Vice President Richard Nixon and the junior senator from Massachusetts, John F. Kennedy, was in its last anxious throes. Whoever prevailed, Cuba would be priority numero uno for the incoming administration. An invasion was probable, cessation of diplomatic relations a foregone conclusion. The American embassy in Havana was already destroying documents ahead of an anticipated withdrawal.

That was bad news for the CIA. Embassies are beachheads, the legitimate cover intelligence agents need to land on foreign soil. And Cuba had just become very important foreign soil. The Russians and Cubans were dancing the mambo, Communist China was knocking on the door, and the CIA was about to lose its invitation to the ball. Teams from Langley had been cycling through Havana for weeks installing bugs and developing assets ahead of an American pull-out. There was so much activity Castro’s ham-fisted G2 couldn’t help getting wise. Audio techs from the most recent operations reported close calls and brushes with death. A few of them flatly refused to go back, putting in for vacation instead. There were whispers around the water cooler that Havana was a suicide mission.

Which is exactly the moment David fucking Christ decided it would be a good idea to play cowboy, one last operation to bug a Havana apartment belonging to the Chinese diplomatic core. Christ had recently been promoted, Mertz knew, which helped explain the disastrous decision to fly into that hornet’s nest with two young agents in tow. An egghead, Christ had spent most of his career designing listening devices. Now he found himself in charge of the guys who planted the bugs. There was lunchroom chatter about his bona fides — or lack thereof. He wanted to prove he could hang.

Mertz’s first order of business was to shore up the agents’ lousy cover. Since news of their capture, he had spent every waking moment soliciting an army of conspirators to make three fake lives seem real enough to anyone who went poking around. Answering services, falsified records, civilians compelled to recall a fake neighbor who lived down the hall in case anybody asked. His efforts were paying off. The men survived a month-long interrogation, and somehow the Cubans seemed be buying the idea they were hapless tourists duped into espionage by American embassy personnel. They were handed ten-year sentences in the Isle of Pines, a fetid prison on a small island just off Cuba’s southwest coast.

They had escaped the firing squad, but the sentence presented a whole new set of problems. Mertz rubbed his temples. Extracting three undercover agents from an Alcatraz-like island prison off the coast of Cuba wasn’t going to be easy. The place was home to murderers and counter-revolutionaries, and it was Castro’s favorite stash hole for political enemies. The young dictator had spent time there himself, along with his brother, after their first failed attempt at revolution. He had made it the crown jewel of his new government’s penal system, a threat to all who sought to depose him. His goons guarded the prison fiercely, which meant going in with guns blazing was out of the question. If an armed rescue failed, which was likely, it would tip the Cubans off that they had someone valuable.

The situation required finesse. It would have to be cash, then. Swallowing hard, Mertz forced the decision down like a mouthful of reflux. Then he picked up the phone and dialed an old buddy. The CIA could never openly admit to dealing with the mafia, but intelligence work was a mixed bag. Mertz’s job was to bring the assets home, and if anyone knew how to lean on a Cuban official, he wagered, it was the mob.

The Cuban military plane rattled to a bumpy landing. Inside, the three Americans traded looks. The plane held six armed Cuban guards and twenty-seven bedraggled prisoners, mostly Cuban. More guards waited outside on the airstrip. The small island they had just landed on had a reputation for being impossible to escape, and the Americans were already weak from their months-long ordeal: interrogation sessions, the trial, weeks of icy nerves thinking about this moment.

Even so, they thought of making a break for it.

The guards ordered all the prisoners to stand, then marched them off the plane in a line. Squinting in the bright tropical sun, the Americans had barely set foot on the dirt runway before they were shoved into a covered military truck, part of a convoy that would carry them to their new home. They were silent on the ride over, guts clenched, replaying overheard snippets about the hellhole that awaited. As the trucks approached the prison, their first glimpse of it was actually a relief, the way the arrival of total disaster sometimes brings contentment: The worst has happened, this is the bottom, there’s nothing left to fear.

Only fear hates being sidelined, so it charged back quickly.

Five separate buildings, each like a fat silo, composed the prison facility. The Americans had cobbled together a sense of the interior layout of each silo from other detainees awaiting transfer. The buildings on the Isle of Pines were panopticons, experiments in authoritarianism. Each held hundreds of cells arranged in a cylinder around a huge interior courtyard where a guard tower resembling a lighthouse rose. Small holes wide enough for gun barrels studded this central guard tower and allowed the guards to peer out. Prisoners weren’t able to see inside the tower, but guards could look directly into any cell at any time. Criminals would be more likely to behave if they didn’t know when they were being observed, the theory went. Awaiting trial, they’d met just one man who served time on the Isle of Pines. The theory was bullshit, he told them. Inmates at the prison never behaved.

After the trucks jerked to a rough stop, the prisoners were unloaded and shoved into a single file at the gaping mouth of one of the cylindrical buildings. Then they were marched inside and stripped naked, their meager possessions confiscated. They pulled on ratty prison uniforms under the searing eyes and scowls of the guards. Finally, they were led into the building’s stadium-like interior.

The first thing they noticed, before the stench or the flies or the slimy floors beneath their feet, was the noise. It was a sound like jets taking off, the bloodthirsty din of the Coliseum resurrected from Roman times and transported to the Tropics. Hundreds of ragged, hopeless men were screaming at the tops of their lungs. The noise reverberated around the hollow structure, feeding on itself.

Gazing up, the Americans saw six stories of circular terraces, each jammed with angry, downcast faces. The building had one characteristic feature few prisons have ever had: There were no interior bars, so prisoners were free to move around the balconies and shuttle between floors as they pleased, always under the watchful eyes of the guards in the looming central tower. The arrival of new meat had drawn all the inmates out of their cells. Though twenty-seven men were being transferred in, the three agents had the distinct feeling the bellowing prisoners above were looking directly at them, casting that hateful, crushing roar their way.

David Christ looked at the two younger agents beside him. He was the leader here. “All right,” he managed with some confidence, “we’re going to be all right.”

The Isle of Pines prison

Wilma Christ had about had it with the little imp from the CIA’s Office of Security. A mother of six, wife of a longtime Agency man, she knew well-enough when someone was lying to her face.

The Agency is doing everything in its power to secure David’s release.

The refrain had all the telltale markers of a throwaway line, a mollifying phrase designed to keep her at bay. Wilma’s oldest son, Thomas, was about to start college, her daughter, Elaine, cried herself to sleep every night after asking about David, and Wilma would be damned if she’d let Fidel Castro or the Agency bureaucracy deprive her kids of their father. She wanted real answers, and she was going to get them one way or another. So after a few weeks of putting up with the imp, she picked up the phone and did something way outside the normal protocol.

“General Carter please,” she said into the receiver. “This is Wilma Christ.”

General Marshall Carter was on his way to becoming Deputy Director of the CIA, and he had the juice to get things moving quickly. Carter, with whom Wilma had shared small talk at Washington social events, made inquiries on her behalf. Soon he was patched through to John Mertz, the man taking point on extracting the captured agents. Privately grumbling about outside interference, Mertz forwarded the call up the chain of command. Owing to the heft of the caller, the message landed on the desk of Allen Dulles, Director of the CIA. Dulles, in turn, invited Wilma in for a clarifying powwow.

On March 28, 1961, Wilma walked into Director Dulles’ office and demanded to know exactly what was being done to free her husband. Dulles apologized. He really couldn’t say much about Mertz’s operation. But after promising her that multiple plans to free the men were being considered with utmost urgency, he said something that stuck with her: The best hope of obtaining David’s freedom “lies in revolution in Cuba.”

Those words would soon come back to her with haunting clarity.

An escalation of shouts intruded on Christ’s depressed thoughts. The persistent din of the prison had reached a new ferocity, if that was even possible.

Christ stood from his bare mattress and made his way out to the interior balcony overlooking the courtyard. From his fifth-floor perch he gazed down on a scene of bedlam. A fight had broken out on one of the lower balconies and was spreading like a fire between the floors. Men screamed, threw bottles, and banged metal buckets. At the center of the cavernous building, the guard tower remained dark. Christ wondered if there were any guards in there at all. They never seemed to be around when things went south. On the other hand, they pounced like clockwork during rare moments of peace, tearing through the prison and tossing cells seemingly out of boredom.

The fight was barbarous: Chains, shivs, and long strips of sharpened rebar emerged from hiding places. It seemed impossible so many weapons had survived the frequent searches, but there they were. Blood splattered over railings and the flat splat of fists hammering flesh echoed off concrete walls. The fight hadn’t yet reached the fifth floor, but Christ braced himself.

The strains of that awful place, where death could come from a guard, a fellow inmate, or even from the gangrenous squalor they lived in, had taken their toll after just a few endless months. Christ couldn’t help noticing the deterioration of his team. Walter Szuminski, 30, was a handsome blond kid with more foreign operations experience than practically anyone else his age in the Agency. He’d been the picture of cool when they started out from Miami, an agent’s agent with a thousand-yard stare and a quiet devotion to his country. Now he looked tired and malnourished. He was still suffering the aftermath of a terrible skin infection, which was only made worse by the constant assault of flies and bedbugs.

Thornton Anderson, 34, was a good soldier who worried about his sons. He was trying to use his Marine discipline to get through each day — up to shave in a cupful of the brackish grey water they carried from a cistern down below, trooping down to the meager breakfast of beans and a dash of milk, exercising throughout the day. Whenever anyone insulted the United States, Anderson was the first to make the man stand behind his words. It was a miracle he hadn’t been killed in his sleep.

Physically as well as psychologically, they were spent. Christ, 42, outranked the others by several rungs, but if he was being honest he didn’t know much about being a leader, especially in a situation like this. He had led them right into a trap during their ill-fated bugging operation in Havana, and now they were stuck in prison with no relief in sight.

Christ was a born scientist, not a field operative. He’d trained in a lab, rose through the ranks as an R&D researcher, and had designed much of the listening equipment the CIA used in its bugging operations. It was a fluke promotion that put him in charge of the men who planted the bugs, and with it came internal grumbling, questions about his competency, hushed talk in hallways. When half his audio techs declined to go to Cuba, calling it a suicide mission, Christ saw an opportunity to change the conversation and stop the whispers. He would prove his mettle, he thought. Now they were here.

As if by some pre-arranged signal, the fight on the floors below stopped. Fists fell, weapons disappeared back into their secret caches, and prisoners retreated to their cells. One man lay dead after the excitement, shanked and resting in a spreading pool of his own blood. The guards, late as usual, made a show of storming in to return order, but the action was all over. It was as if a great wave crested and crashed, leaving behind a flat, calm sea. Thousands of eyes blinked out of the dark cells, awaiting the next storm.

Now what? Mertz thought. First Wilma Christ goes off the reservation, inviting all kinds of attention from management, and next his big plan falls flatter than a high schooler’s suggestion of a back-seat romp.

Mertz had authorized one of his contacts, a federal drug cop with a Rolodex full of unsavory characters, to spend up to a million dollars enticing some wise guys in Miami to grease the wheels and apply some muscle in Cuba to free the CIA agents. The mobsters whistled at the money but laughed at the request. No go, Mertz’s contact reported back. Castro’s revolution had been as much a strike against the stranglehold of American interests — especially gambling interests — as an ideological crusade. When Havana fell, mafiosos were rounded up or chased out with their tails between their legs. Even the mob had no pull in Castro’s Cuba.

But the trip to Miami wasn’t a complete waste. Mertz’s contact had another idea: A resistance movement was growing in Miami, and one of its central figures was the former driver for Fulgencio Batista, the ousted Cuban president. “The Chauffeur,” as the driver was known, was said to be well connected.

Mertz flew to Florida and met the diminutive, well-dressed Cubano over dinner. “We’ll get them out easy,” the man said, smiling confidently. That made Mertz skeptical. Nothing about Cuba was proving to be easy. The Chauffeur insisted his network was in touch with guards at the Isle of Pines, that they’d gladly walk the agents out the back door during work duty. From there it was just a ten-mile jaunt to the southern end of the island, where the resistance would have a boat waiting. The plan would cost the CIA $200,000 upfront, The Chauffeur said matter-of-factly, as if reciting the market price for the day’s fresh catch.

Mertz thought it over in his hotel room. Bullshit. It felt like a con. Sure enough, the plan fell apart under further scrutiny. The ten mile stretch between the prison and the island’s southern shore turned out to be an impassable mangrove swamp. Even if the chauffeur did have contacts in the prison, the Americans would likely be too weak to make the trek. Thanks, but no thanks.

His lousy options dwindling, Mertz had another card to play. A field station in Mexico had unearthed a Mexican lawyer who was supposed to be tight with the Castro brothers. For the right price, with the right access, anything in Cuba could be purchased, the lawyer explained — even the freedom of American prisoners. Mertz’s mind reeled at the idea: bribing the Castro brothers to let three CIA agents go free before the Cuban security service could figure out who they were.

Well, what the hell? Everything else was through the looking glass when it came to Cuba. Mertz couldn’t tell the lawyer exactly who it was he needed freed without tipping the CIA’s hand, so he instructed the man to try and buy the freedom of dozens of captured Americans at once, Christ, Anderson, and Szuminski among them. The lawyer collected his retainer and promised to go to work on the bribe immediately.

Maybe there was some hope of a painless resolution after all, Mertz thought — just so long as no one tried anything stupid.

He should have known better. On TV, a massive story was just breaking. Every newscaster in the world was suddenly talking about Cuba.

Cuban soldados defending against Bay of Pigs invasion

“It’s a .50 caliber!” Szuminski called, rushing into the adjacent cell, where Christ and Anderson had just sprung out of bed.

All three flung themselves toward the barred exterior window to see what was happening. It was night, and through the bars they could make out the unmistakable traces of a firefight in the distance. Moments later, the entire prison began to shake as several military planes barreled in low overhead.

Christ broke out in a smile. What were the odds they’d be able to see the American-backed invasion from their cells? He clapped the others on the back. They’d been in prison four months. At long last, Uncle Sam was about to spring them.

The three got one last look at the sweet sight playing out a few miles across the dark water before a volley of shots sent them to the floor. The guards were firing indiscriminately from the central lighthouse. Then there was shouting in Spanish, the heavy footfalls of boots, orders to stay away from the windows. The Americans passed the rest of the night on their bellies before being herded downstairs. Under a bombardment of shouts and threats from the guards, they remained standing in their underwear for hours with no food or water. Anyone who spoke got a quick rifle butt to the belly.

None of it mattered, not to Christ. He was radiant with the knowledge that Castro would soon be deposed. Before leaving for Cuba, he had received a terse message to pay a visit to the Director’s office. The air in the room was tense as he settled into a chair. Perhaps it was something about his job performance? No, it turned out to be a briefing. An invasion plan was in the works, and Christ, newly ensconced as head of the Audio Operations Branch of the Technical Services Division, was being read in. The CIA was training Cuban dissidents on a private island off the coast of Miami, he was told. They would land by sea at an undisclosed location and fight their way to Havana with American-backed air support, gaining followers and gathering strength from the local populace. The invasion would start a counter-revolution, and Castro would be driven out. The operation, a closely guarded secret even within the CIA, had approval from the highest office. Their bugging team’s mission would be a piece of the puzzle in the plan to get a jump on Castro.

In the back of his mind, Christ had been replaying that briefing since their capture, unsure if the invasion plans would ever go into effect. For security, and to give them plausible deniability during interrogations, he couldn’t tell the others, but he had been nurturing the hope that a group of well-armed Cuban rebels would land on a beach any day. Now it was happening just a few miles across the water, and it was only a matter of time before Castro would be toppled. They would soon be heading home.

Meals were canceled for three days. On the fourth, a familiar guard walked by the cell. The Americans took a chance and asked what was happening. The guard shrugged. They tried to invade, the man said. Then he broke into a smile that shattered Christ’s heart into tiny pieces.

“But Fidel was ready.”

The guard standing at the door of Fidel Castro’s Havana residence on the evening of April 17, 1961, was startled by a man from the defense ministry, who ran right past him and into El Comandante’s home. The official was waving his arms and yelling “Playa Giron! Playa Giron!

If that man had been an assassin, the guard thought, he would have slipped right through. He had better pay closer attention, in spite of the languorous evening heat. Everyone had to do their part for the revolution.

Inside the residence, Castro received the update from the defense official with a mix of excitement and anger. Airplanes disguised as Cuban Air Force assets — no doubt American decoys, Castro presumed at once — were attempting to bomb Cuba’s air defenses. Either due to a lack of skill on the part of the pilots or good luck on the part of the Cubans, nearly all the bombs missed their mark. The aerial bombardment was the first phase of a coordinated attack. Elsewhere, an invading force of 1,200 trained Cuban exiles previously living in Miami was making landfall at Playa Giron, the Bay of Pigs, intent on bringing about a counter-revolution.

“What fools they are!” Castro thundered triumphantly.

Unknown to the American planners, the Bay of Pigs was one of Castro’s favorite fishing spots. He knew the secluded beach on the country’s southwest coast well, and he had a good idea how to defend it. Castro left his home in a hurry to take to the airwaves. The test he had been predicting would come for so long was upon them. If his young revolution was going to survive, his Cuban brothers and sisters would have to rally to the cause of national defense. The Yankees, too scared to fight him themselves, had sent exiles to do their bidding, and it was up to the patriots who stayed on the island to stop them.

Rally them he did. Marshaling Cuba’s armed forces, supplementing trained soldiers with thousands of lightly armed campesino volunteers, men and women willing to bleed for the revolution, Castro surrounded the invaders. In less than 24 hours, more than 100 counter-revolutionaries were dead, the remaining 1,100 in captivity. Castro was jubilant. Not only had the Americans tried and failed to invade the island by proxy, but they did it in blundering fashion that exposed their lies and hypocrisy to the whole world. Papers carried photographs of the disguised planes, clearly American B-26s, and Castro dispatched his cabinet to orchestrate an international media blitz.

Fearing a second attempt, Castro’s next order of business was to secure some leverage against the Americans to prevent another invasion. The Isle of Pines prison was crammed full of dissidents and enemies of the state, men who longed to see Castro and his kind driven out. Some of those men had been prominent leaders of anti-Castro movements. If the Americans hoped for counter-revolution, their best bet would be to free the prisoners in the Isle of Pines, who would form the vanguard of the fight. The location of the failed invasion suggested that the prison might even have been one of the invaders’ planned targets.

Among the thousands of accused enemy collaborators, Castro was also confident his security forces had rounded up at least a few authentic American assets, men whose lives President John F. Kennedy would be loath to sacrifice, especially after the humiliating Bay of Pigs defeat. Castro had survived the first invasion attempt, and now he decided to issue himself a little insurance.

Calling on a top general, he outlined his plan. The Isle of Pines would be wired for destruction, rigged to blow on his order. Boxes of dynamite were loaded onto a cargo plane destined for the prison. Castro returned to his residence in a buoyant state. Everything seemed to be going his way. Even the guard at his door seemed to stand a little more at attention than usual.

The first giant air compressor showed up about a week after the invasion attempt. The contraption ran from morning to evening powering pneumatic drills, and for several days the sound of the bits chewing into concrete filled the tower where the three Americans were being held.

Christ could guess easily enough what Castro’s men were up to. Other prisoners took longer to figure it out or admit it to themselves. Cubans had a special talent for denial, Christ noticed. He marveled at how even intelligent men could watch Cuban soldiers troop in with boxes marked mecha explosivo — explosive detonating fuse — and still doubt their squalid hellhole was being turned into a giant bomb.

A herd of covered trucks pulled up one evening. With an air of extreme caution, Castro’s soldiers began unloading boxes. After emptying them of their contents, they hastily tossed the cartons outside the entrance of the tower, where the prisoners spotted them the next morning. Any denials were put to rest. Each box was stenciled: TNT.

Christ did some math. He guessed each box held approximately 50 pounds of dynamite. That meant their building was now crammed with about five tons of high explosives. Soon after, guards dispersed black plastic rings etched with white numbers. When the merciless hand of the revolution came down on the plunger, the rings would be the only way to identify bodies — or whatever remained of them. Some prisoners refused to wear the ID rings, so the guards began hastily tattooing numbers into their skin. They were being marked for death, corpses in waiting.

In the abstract, the lives of the prisoners had always been in Castro’s hands. Now, Christ realized, the young revolutionary, who was stepping up executions across the country, was in possession of a way to blow them all to hell at a moment’s notice and in a very non-abstract way. One more invasion attempt and they’d be goners. A simple change of mood or perceived slight from abroad could send Castro into a tizzy and blast them into pieces. They had become chips in a high stakes game of geopolitical poker.

Schemes of sabotage started almost at once. Various factions within the prison jockeyed to take the lead on a covert defusing effort. Ex-Batista soldiers campaigned against pro-Castro groups, as if suddenly thrust into a general election for the fate of the prison. Most of the prisoners wouldn’t have known a stick of dynamite from a link of sausage, but that was a minor detail. Pride was at stake, along with the lives of more than six thousand men.

Faced with the prospect of letting Castro blow the place up on one hand or watching a group of bumbling prisoners expedite it on the other, a former Cuban Air Force officer with a knack for leadership united the quarreling factions and, over some grumbling dissenters, took control of the effort by near unanimous decision. Captain Miro was stoic for a Cuban, with a booming voice that made him a natural commander. His first order of business was to recruit prisoners with needed skills, particularly anyone who might know anything about covert operations and explosives.

Miro’s gut told him to consider the handful of Americans in the Isle of Pines, mostly a thoroughly disreputable bunch. One, John Martino, was affiliated with Santos Trafficante, the mobster. Another, a talkative inmate named Leslie, had landed in Cuba as part of a plot to overthrow the dictator of Nicaragua before things went sideways. When he first got to the Isle of Pines, he had refused to bathe, eventually setting a prison record by going a full year without visiting the showers. When he eventually broke down and sulked downstairs, towel in hand, the inmates in the tower erupted in applause.

But the three inmates on the fifth floor weren’t like those others. Whether through instinct or some perceived crack in their cover stories — mild-mannered engineers on vacation, they maintained — Captain Miro believed they were just the sort of men who might know how to pull off an operation like the one he envisioned.

On Wilma Christ’s TV set, American Ambassador Adlai Stevenson was fervently denying American involvement in the failed invasion before the UN general assembly. In Cuba, foreign minister Raul Roa was presenting casings from American rockets fired in the salvo prior to the invasion. In newspapers around the world, editors ran photographs of American B-26 bombers dolled up to look like Cuban Air Force planes, a sleight of hand that fooled no one except, perhaps, Ambassador Stevenson, who was beside himself with rage when he learned he’d been unwittingly recruited into a sloppy cover up.

CIA Director Allen Dulles’ veiled comment drifted back to Wilma: David’s best chance for escape lies in revolution in Cuba. The CIA had been behind the invasion, Wilma was sure. In true Agency fashion, they’d gone in confident and bungled it from launch.

She had to continue to go up the chain of command to try to get her husband back. Opening her Rolodex, she plucked out another of the hundreds of business cards she’d collected during her husband’s years-long march into the CIA’s upper ranks. This one belonged to Charles Pearre Cabell, Deputy Director of Central Intelligence. “I demand to speak with the president,” she told Cabell when she finally got him on the line.

If the demand seemed outsized, so was Wilma’s ace in the hole. With the failed Bay of Pigs invasion, the CIA had just embarrassed the United States in spectacular fashion. If Wilma went to the press with a story about her husband and two other captured CIA agents serving time in a Cuban prison after a failed bugging operation, reaction from the Kennedy administration would be swift and damning. The leaked news would further humiliate the Agency and the country, putting pressure on President Kennedy to negotiate the men’s release, whatever the cost.

At least, that was the longed-for outcome. On the other hand, going to the press could backfire. According to the darkest legends about the CIA, she could end up disappeared. And as soon as Castro’s goons figured out who they had, the agents were sure to be tortured. Her husband, the senior man in the trio, would get the worst of it. Christ had intel on all Agency bugging operations worldwide, knew the locations and true identities of every audio technician on assignment. To make matters worse, in his previous role with the Applied Physics Branch he’d directed R&D activities on several spy technologies that were now critical to Agency operations. He had encyclopedic knowledge of the CIA’s cutting-edge listening equipment, much of which he’d designed. The Cubans would try to wring that information out of him like water from a towel, then use it as currency with their new patron, the Soviet Union.

For moral support, Wilma had her husband’s brother, Lawrence Christ. Communicating with the Office of Security, Lawrence repeated Wilma’s demand to be put in touch with the White House. Upping the stakes, he suggested Wilma was at the end of her rope and on the verge of a nervous breakdown. They had better act fast if they wanted to keep the matter out of the press. “They have time to greet astronauts, foreign dignitaries and the like, yet they cannot even call her on the telephone!” he barked, sloughing off the suggestion that administration officials were too busy for meetings.

Director Dulles attempted to mollify Mrs. Christ by urging prudence, and then by approving a college scholarship for her oldest son, Thomas. The offer came via Dr. Sidney Gottlieb, a longtime colleague of David’s. A chemist and the CIA’s foremost expert on poison, Dr. Gottlieb had recently been working on various schemes to humiliate Fidel Castro, including by lacing the television studio where he recorded speeches with LSD and putting the chemical thallium on his shoes so his beard would fall out. Gottlieb was also investigating several methods to assassinate the Cuban leader following the Bay of Pigs fiasco, including by means of poisoned cigars and exploding conch shells. For the moment, though, his attention was diverted to helping his employer control Wilma Christ.

“Although this request is in part motivated by compassion for the Tech’s families and a strong desire to lighten their burden,” Gottlieb wrote in a memo to the Deputy Director in his request for special funds for the scholarship, “the overriding consideration is the need for continued operational security and control, which will be aided by your approval of our request.”

Wilma wouldn’t relent. Cornered, the CIA had no choice but to arrange a meeting. In December 1962, Wilma was invited to sit down with U.S. Attorney General Robert Kennedy, where she was briefed on plans to send a U.S. delegation to Cuba to begin negotiations with the Castro government. The objective of the negotiations was to free the 1,100 captured Bay of Pigs rebels. At her insistence, Wilma was then granted a meeting with the man leading the delegation, James Donovan, a prominent New York lawyer who had just negotiated the exchange of a captured Soviet spy for downed American U2 pilot Francis Gary Powers (a diplomatic coup de grace later dramatized in the film Bridge of Spies).

In December 1962, Wilma met with Donovan and pleaded with him to secure the release of her husband and the other captured CIA men. Donovan, accustomed to bailing his government out after national screwups of epic international proportions, listened to the tale of heartache with compassion.

Bay of Pigs prisoners

Captain Miro’s proposal posed a dilemma for Christ, Anderson, and Szuminski. Keeping a secret at the Isle of Pines was about as hopeless as keeping the bedbugs at bay. As soon as any operation to thwart the explosives commenced, every inmate in the tower — and soon the entire prison — was sure to know about it. If a group of Americans took the lead, word would spread twice as quickly.

It was imperative the CIA men maintained their cover. If their special expertise became common knowledge, and if that knowledge made its way from the prisoners to the guards to Castro’s soldiers, it was very likely a revision to their sentence would be in order, a new round of interrogations opened, and a firing squad prepped.

Then again, if they didn’t lead the mission, it was also likely 6,000 men would be blown up — either by Castro or through some bungled operation run by a bunch of would-be heroes. For Christ, the decision was also deeply personal. He had led his men into this. Perhaps by helping save the day now he could, in some way, make up for that failing. They were in, he told Captain Miro, without letting on how uncanny his instinct was.

The former Cuban Air Force officer had also assembled a ragtag crew of other inmates to assist in sabotaging the explosives. Among them was a street-smart wisp of a kid nicknamed Americano, who had a good handle on gossip in the joint and whose diminutive size would soon prove useful. There were also Manolo and Biscayino, friends who never went anywhere without one another, an arrangement made odd by Manolo’s morbid obesity and Biscayino’s notable svelteness. Then there was Raul Capote, an ex-Batista army man who was as debonair as an old silent movie star. They also had in their crew a fiery student activist named Pedro Luis Boitel and a nervous wreck named Ulysses Silva, who, despite his reputation, showed real cajones during a failed escape attempt some weeks earlier. Miro also unofficially commanded a small group of ex-Batista soldiers, along with a few less reputable men drawn into his orbit and deemed loyal enough given the circumstances.

Castro’s soldiers had installed the explosives in a utility tunnel below the prison. One of Miro’s men had discovered a small rat hole drain in the first-floor lavatory that led into the utility tunnel. Guards went out of their way to avoid the putrid toilets, so it made an ideal access point.

The duo of Fat Manolo and Skinny Biscayino volunteered to enlarge the hole. The two men used improvised hammers and chisels to chip away at the concrete behind the toilet. The ungodly noise in the tower — the roar of hundreds of men shouting and clanking pipes with their fly-covered dishes — helped disguise the work, and after a few days the hole grew from five inches in diameter to a little over a foot. It was laughably narrow for a fat tub like Manolo, and too small even for Biscayino, but the dimensions of the bathroom prevented them from enlarging it further. The mission hinged on finding someone small enough.

Miro approached Americano, the fair-haired, street smart kid who knew the prison inside and out. He was small, barely more than a hundred pounds in a frame that didn’t stretch past five feet. He was also bright and articulate, an ideal scout. He was too bright, it turned out. The kid turned the job down flat. Rounds of cajoling, threatening, and pleading followed. It wasn’t until Americano met the three Americans, who confirmed they were now running the operation, that he gave in. The Americans lent the mission some gravitas. With Americano’s loose consent, the scouting operation was ready to move forward, and the kid allowed himself to be hustled into the bathroom and practically shoved through the tiny hole.

Manolo and Biscayino had been monitoring activity in the tunnel. Noon, when the soldiers napped or ate lunch, was the best hour for a scouting run, though the timing had to be precise — any more than 15 minutes and the guards were likely to return. Americano dropped through the hole a little before noon. He found the tunnel surprisingly spacious, tall enough for a bigger man than himself to stand in. It was dim, though, and he had trouble seeing. Skulking along by feel, spinning at every drip of water or clank in the overhead piping, he allowed his eyes to adjust and began making mental notes of what he observed. Large concrete columns supported the tower above. He saw that narrow holes had been drilled in each and the columns were wired together like telephone poles. Americano felt around inside the holes in the concrete until his fingers found a substance like putty. The smell emanating from the holes was of cloying fruit. Each column was jammed full of the stuff.

Anxious to get out before the soldiers returned, the scout made his way back to the access hole. Climbing up the tunnel’s slick walls and getting his head through, he suddenly became stuck. His feet flailed in the tunnel below as his accomplices worked to pull him back up into the bathroom. The clock was ticking; it was now well after 12:15. After what felt like an eternity, Americano’s slender hips jiggled free. He collapsed on the bathroom floor, panting and exhausted, quaking from fear. When he recovered his wits, he relayed what he’d seen. He could tell from the faces of the three Americans that the news he delivered wasn’t welcome.

Christ consulted with Miro. The soldiers had rigged the dynamite with some sort of failsafe detonation system. In addition to electrical line running to the TNT through dedicated channels drilled through the columns, the soldiers had installed a second channel with high-grade primer cord — a kind of high-speed fuse ignited with a blasting cap. If the electrical detonation system malfunctioned or was tampered with, the Cuban soldiers could ignite the primer cord from a shed a half-mile from the prison. Sabotaging one system wouldn’t be enough. They had to find a way to disable both detonators.

And there was a catch: They had to do it without anyone realizing the detonation systems had been tampered with. Simply cutting the cords wouldn’t do. The electrical circuit would likely be inspected regularly with a galvanometer, which measures current. The lines were sure to be physically inspected, as well, and if the Cubans found any slack, any sign of sabotage, they’d turn the whole prison upside down, find the access hole, and ensure the prisoners didn’t get a second chance.

The saboteurs needed more information. Americano reluctantly went back into the tunnel the following day and pilfered samples of blasting caps and primer cord, which he found piled around on the floor. On a subsequent trip, feeling braver, he managed to steal several blocks of malleable TNT. He hoped to keep some as a souvenir, but Christ had a better idea. If the order to blow the prison came down, the Cubans would expect an explosion. Sabotaging the bomb would buy some time, but only a little. The prisoners needed to be prepared for a suicide jailbreak, and that meant making weapons to arm their fellow prisoners. With dynamite and blasting caps, they had the essential ingredients for grenades.

Christ, the consummate scientist, was now in his element, and he began drawing up plans. A team led by Szuminski was put to work filling out an improvised prison armory. The prisoners operated in shifts, always away from the main action in the prison. Backs turned, but always in sight of the looming central guard tower, they toiled with every expectation they’d be noticed and shot any moment. Empty cans of condensed milk served as grenade bodies. Using an improvised double boiler, the prisoners carefully melted the pilfered TNT and poured it into cans. Rocks and nails were added for shrapnel, the cans topped with blasting caps.

The prisoners made their own fuses by tediously cutting the heads off matches and grinding up the powder, which they placed in scraps of tubing from the infirmary. The operation ground to a halt whenever one of the prisoners handled the match heads too roughly, setting a flash of powder off in someone’s face. Somehow the multiple singed eyebrows didn’t give the operation away, and the prisoners had the sense the guards were getting cocky. To test the fuses, the prisoners lit a few and dropped them down the central shaft. They were delighted that they stayed lit.

Encouraged by Christ, a Cuban prisoner with chemistry experience came up with the idea of making alcohol for Molotov cocktails. Fruit scraps were fermented in a jar and then cooked in a pressure cooker floating around the prison. Intravenous tubing was run from the pressure cooker through a tub of water and into a collecting can. The output was distilled several times, and the chemist guessed the final product was at least 170 proof, plenty flammable. Rags were torn, bottles filled, and more than a few of the Molotov cocktails tilted in unsanctioned celebration.

In his spare time, Szuminski began working on a flamethrower, which he improvised from one of the prison’s kerosene lamps. He used marble dust and toothpaste to grind brass parts so they’d form an airtight seal. Pumping up the tank with air, he managed to produce a solid stream of fuel, which could be ignited with a lighter.

Anderson, meanwhile, drew a detailed map of the prison and Castro’s dynamiting operation on onion skin paper, which the crew managed to smuggle out during visiting hours with help from the girlfriend of an inmate. Through a network of counter-revolutionaries, the map made its way to Miami and finally on to CIA headquarters, where it was promptly cataloged, placed in a filing cabinet, and forgotten.

Experimenting with the pilfered materials, talking long into the night, Christ and his crew worked out a promising strategy to defuse the explosives. Thanks to their experience working with audio equipment, they found a simple solution to the electrical failsafe system. After slicing and pulling back the outer insulation on the triggering wires, they could cut the two inner wires, cross them, and then let the outer insulation slip back into place. The system would send current and still pass a galvanometer test, but the circuit would short out under load. Crucially, the wire would look and feel intact under physical inspection.

The primer cord was trickier. Christ, tinkering with the little treasures and bits of debris inmates had donated to the effort, eventually solved it using a sewing spool and several pins. The cord ran through a channel of thick plastic insulation, which the saboteurs first had to sever. The primer cord could then be sliced and attached to the end of a sewing spool with pins. The two ends of severed outer tubing could then be pushed together over the spool and held in place with more carefully concealed pins. The system would appear to be in good working order in the dark tunnel, and the primer cord within would withstand a probing tug. The gap introduced via the spool would keep the explosives from detonating.

Figuring out a working plan and performing that plan in the field under pressure where different things. The agents summoned Americano. He needed to be able to perform all of these delicate tasks in the dark and against a ticking clock. For four nights they worked with him in a cell, running the operation over and over. They blindfolded him with a blanket and had him repeat the wire twist drill and the spool trick until they were out of materials and his hands were bloodied from pin pricks. He wouldn’t be able to make a sound, he was instructed, and if he was captured, he’d likely face years of solitary confinement — or, if he was luckier, instant execution.

Keeping abreast of activity in the tunnel, Manolo and Biscayino surmised the soldiers were nearly finished installing the last of the dynamite. The bomb would be live then, their lives in Castro’s hands. The decision was made to proceed. Americano would go into the tunnel an hour before final count for bedtime, when it would likely be deserted. It was the best time to avoid a run-in with a guard, but if he didn’t make it back in time his absence would be discovered during nightly count.

Americano slipped into the hole. Christ, whose redemption was at stake in the sabotage operation, had never been more nervous. Looking at Anderson and Szuminski, at Miro, and at the assortment of oddballs and undesirables who came together for the unlikely mission, he was overcome by a feeling of kinship. In spite of it all, they were surviving, and the odd alliance gave him faith in himself and the future.

At last Americano’s head emerged from the hole just as the whistle blew for the nightly count. Too scared to utter a word, Christ made a questioning gesture with his hands. Americano grinned and nodded his head.

Detailed instructions were transmitted via a network of prisoners from one tower to the next. The saboteurs who came up with the defusing method were tense for days, sure someone in one of the other four towers would slip up. All hell would break loose if that happened, and they’d have to use their cache of improvised weapons. Minutes ticked by slower than hours, with everyone waiting to spring into action.

But word came back one by one: the teams in each of the other towers were successful. Christ gazed out the window of his cell and saw the Cuban soldier whose job it was to check the blasting wires running from the towers to a guard shed. As he had each morning for the past few days, he placed his galvanometer against leads and seemed satisfied with the results. If the soldiers attempted to detonate the prison, Christ reasoned, the guards would give them a heads up by fleeing. It would be a narrow window, but it would be just enough for them to escape. Even if they didn’t, perhaps the averted disaster would give Castro enough time to cool off, reconsider, and recall his murderous orders.

James Donovan was tired, and now all his careful legwork seemed destined for the scrapheap of history.

No sooner had the New York lawyer returned from successfully negotiating the prisoner swap of American U2 pilot Francis Gary Powers for Soviet spy Rudolf Abel in February 1962 than President Kennedy came calling. Would he do the same thing in Cuba — only on a much grander scale?

More than a thousand Bay of Pigs invaders had been captured in Cuba. Following the international embarrassment of the failed attempt at overthrow, it was a matter of American honor for Kennedy to get them back unharmed. The CIA had failed dramatically and publicly, and now the president needed Donovan to pick up the pieces.

The Powers negotiations had taken all of ten days but talks with Cuba dragged on for months. Donovan, a keen study of personalities, knew that Castro would have to trust him fully before he’d be willing to negotiate seriously, so the lawyer began the arduous task of building rapport during regular trips from New York to Havana, where the sweltering tropical heat always walloped him stepping off the plane. He sat with Castro more than a dozen times, building a relationship, listening to concerns, even deigning to interrupt the Cuban leader when he tended to pontificate on a point Donovan considered settled. It was a risky demonstration of familiarity, but it worked. Soon Castro invited Donovan on a cross-country road trip, where he boasted about the positive developments in his country since he’d taken power. Castro was beginning to respect him, even show off for him.

And then it all came to screeching halt in October when the Soviets installed nuclear missiles in Cuba, prompting Kennedy to issue orders for a naval blockade of the island. The Cuban Missile Crisis lasted 13 days, during which Donovan fitfully paced by the phone. When the stress finally subsided, bringing a global sigh of relief, Donovan rushed back to Cuba. As a gesture of good faith, he brought along his 18-year-old son. Donovan pleaded with Castro not to let the recent diplomatic crisis derail what had been a fruitful bargaining process. He reminded the Cuban leader that cooperation with the United States was in his best interest, that he could use his position to extract tremendous concessions from the Kennedy administration if he would only play ball.

Castro, whose wry humor had evidently survived the traumatic two-week ordeal when the world stood on the brink of destruction, chuckled at Donovan’s mounting anxiety, then took the lawyer and his son fishing at one of his favorite spots: The Bay of Pigs.

Fidel Castro & James Donovan during negotiations over the fates of the Bay of Pigs prisoners.

Christ heard an excited roar inside the prison. It was March 1963, more than two-and-a-half years into their ordeal. Unsure what was happening, he edged to the railing and peered down. A guard was calling out names, all of them American. Their aliases were among those being read off.

This could be it, he thought. Perhaps Castro had finally decided to exterminate the Americans instead of using them as leverage. In all likelihood, they were being marched to a firing squad right then and there in the courtyard.

What happened next was surreal. Prisoners slapped the three of them on the back as thunderous applause and shouts of congratulations filled the tower. Though they hadn’t quite realized it, the three, so maligned when first processed into the prison, had become heroes to the men around them. Every inmate seemed to know about the sabotage mission. It was a victory against Castro at a time when nobody — least of all the US — seemed capable of one. Rumor had it the operation was even being whispered about in the streets of Havana, a kind of rallying cry for the opposition. That the guards somehow remained oblivious only added a sense of divine providence to the episode.

Christ was first downstairs, ready to meet his fate bravely. His men followed close behind, the three resolving not to show any fear. Reaching the bottom floor, they took one last look up at hundreds of applauding men giving them a standing ovation. Christ knew some of them very well by now. There was a good chance they were saying goodbye forever.

The Americans were led outside, then over the small footbridge that spanned a moat, where the bodies of condemned men were tossed after execution.

Only it wasn’t a firing squad awaiting them on the other side. It was a balding, sharp-eyed lawyer.

James Donovan had understood that in order to successfully negotiate the release of the more than one thousand Bay of Pigs prisoners — to say nothing of the three captured CIA agents, knowledge of whom he’d kept tucked in the back of his mind throughout the negotiations with Castro, ever since his emotional meeting with Wilma Christ — he would need to find a lever, something to offer the Cubans that they couldn’t find elsewhere.

He found it before his last trip to Cuba while playing a Saturday afternoon game of gin rummy with the president of Pfizer Pharmaceuticals. Medicine, the Pfizer executive said. Medicine and food. Donovan knew instantly that such a simple, yet profound, offer would appeal to Castro’s sense of welfare for his people. He put together an offer worth $53 million in food and medical aid and presented it to Castro. Three days later, on Christmas Eve 1962, prisoners from the ill-fated invasion received word: They would be set free.

For good measure, and without authorization from Kennedy or anyone else, Donovan asked Castro for the additional release of close to nine thousand detained relatives of the Bay of Pigs invaders, along with a couple dozen American prisoners rotting away in Cuban detention. Owing entirely to the trust Donovan had carefully built with Castro over the previous long months — an almost supernatural feat following the CIA’s various and continuing failed assassination attempts and plots to foment a counter-revolution — Castro agreed.

Inside a prison annex building, Donovan addressed the prisoners. They were going home, he said. Christ, Anderson, and Szuminski couldn’t believe their ears. After all of it — their failed bugging operation, their day-to-day fight for survival in the Isle of Pines, the Bay of Pigs disaster, the Missile Crisis, and their heroic and successful attempt to disarm the prison and prepare an armed escape — it was diplomacy that was bringing them home.

Everything began to move quickly after that. Guards retrieved the prison uniforms and the Americans climbed aboard a ferryboat pointing promisingly away from the Isle of Pines. Soon the dreaded towers were specks receding on the horizon. After a short stay back at the temporary prison where they’d awaited trial — a veritable hotel after their recent digs — the freed men climbed aboard a plane bound for Miami. Once airborne, Szuminski was informed his mother had died during his detention. The unexpected news brought him to tears, and Christ and Anderson, who had become close with their colleague throughout their ordeal, cried with him.

After the plane landed, intelligence officers hustled the three CIA agents away from the waiting cameras. There was some concern they may have succumbed to brainwashing and were now double agents, so their reception was tepid. Subjected to a battery of polygraph tests and hours-long interviews, it was weeks before they were finally cleared and debriefed, and then allowed to return to the CIA’s Washington office, where they regaled colleagues with stories of their harrowing adventure.

Reunited at last, Wilma revealed to David the tale of her behind-the-scene efforts. Christ told her his own story of the brave men in the Isle of Pines. Husband and wife had both acted with courage and honor, and each was proud of the other. Szuminski spent the period after his release reconnecting with his father and mourning his mother. Anderson also reunited with his wife and sons, proud to have maintained his resolve and patriotism through the interrogations and imprisonment.

Anderson and Szuminski both eventually returned to operational duty. Christ was reassigned to the Directorate of Science and Technology, where he was kept far away from field operations. It was just as well. He had nothing more to prove. Despite their early foul up in getting caught, the three men had maintained their cover for 949 days of Cuban detention, kept morale high under the worst conditions imaginable, and took extraordinary risks to save the lives of their fellow inmates. They did it all with the unwavering faith, sometimes warranted, that their country had their back.

GREG NICHOLS lives on a big sailboat with his wife and kids, writes wild tales of true adventure like this one, and edits with a cutlass. He’s co-founder of Truly*Adventurous.

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Truly*Adventurous

Truly*Adventurous is a media company conceived in a spirit of adventure and built with reckless faith in the power of punch-’em-in-the-teeth longform storytelling. We commission original true stories from the world’s best nonfiction artists.

Greg Nichols

Written by

Nonfiction storyteller. Lives on a sailboat, crashed a motorcycle, and edits with a cutlass. Co-founder @trlyadventurous.

Truly*Adventurous

Truly*Adventurous is a media company conceived in a spirit of adventure and built with reckless faith in the power of punch-’em-in-the-teeth longform storytelling. We commission original true stories from the world’s best nonfiction artists.

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