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 major concern within the agency that they may have succumbed to brainwashing and were now double agents, so their reception was tepid, at best. “They were ostracized,” one direct family member recalls, “even after passing multiple, grueling polygraphs. ‘Management’ was convinced they flipped and were double-agents. They thought there was no way they maintained such a flimsy cover for two-and-a-half years in those circumstances. Their immediate supervisor threatened to fire anyone who spoke to them.”

It would be another sixteen years before the three finally got the internal respect and recognition they deserved for their heroics when they were awarded the Distinguished Intelligence Cross, the CIA’s highest decoration.

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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