How a drifter from Milwaukee became the chief executioner of the Cuban Revolution—and a test case for U.S. civil rights.

By Tony Perrottet

Part One

On the balmy night of April 9, 1959, a little over three months after Fidel Castro and Che Guevara seized power in Cuba, a group of famous international writers gathered in El Floridita, a popular restaurant in Old Havana. They were an urbane set—Tennessee Williams, George Plimpton, Elaine Dundy, and her husband, Kenneth Tynan—and they were expecting to carouse with Cuba’s most beloved yanqui, Ernest Hemingway. Instead, they encountered another Midwestern expatriate, wearing a wide military belt and a hulking .45 service revolver.

Burly and tattooed, the man had rough-hewn good looks. He was in his late thirties—more than two decades younger than Hemingway—and stood five-foot-ten, with thick brown hair and, in the words of his draft card, a “ruddy” complexion. An English journalist later described him as “tall, straight and meanly friendly,” with striking blue eyes that, “yellowing after only a few beers, suggested company dangerous to keep when drunk.” The American’s words tumbled out in the distinctively nasal accent of someone from blue-collar Milwaukee. He pronounced “that” as “dat” and dropped his g’s. He was the uneducated son of Polish immigrants, the type of man one of Williams’s own fictional snobs might have called a redneck.

But if his origins were humble, at El Floridita the man needed no introduction. His image had appeared on the front pages of newspapers across the United States. In fact, after Hemingway, he was probably the most notorious American in the Caribbean. His name was Herman Marks, and he had risen through the ranks of Castro’s rebel army to command the revolution’s firing squads. Around Havana, there were rumors that he had a sadistic streak; his version of a coup de grâce, it was said, was to empty his pistol into a condemned man’s face, so relatives could not recognize the corpse. Marks’s brutal work had earned him a nickname: He was El Carnicero—the Butcher.

The literati peppered him with questions, and Marks responded with pride. He boasted of being second-in-command to Che himself at La Cabaña prison, and declared that he was so busy, he conducted nightly executions until 2 a.m., and sometimes until dawn. He called the proceedings “festivities” and showed off his cuff links made from spent bullet shells.

Marks knew what the gathered writers were really after. It was an open secret in Havana that he invited select visitors to the executions, which were conducted in the empty stone moat around La Cabaña, beneath a giant floodlit statue of Christ with outstretched arms. American politicians, journalists, starlets, and socialites had all made discreet inquiries about watching a firing squad do its work. Williams, whose grandfather had been a minister, forlornly felt that he might comfort a condemned man by offering “a small encouraging smile” before he was shot.

On this particular night, Marks told the group at El Floridita, he had a busy schedule. The prisoners awaiting execution included a German mercenary. “He made the invitation as easily as he might have offered a round of cocktails at his home,” Plimpton later recalled. Marks counted the visitors out: “Let’s see… five of you… quite easy… we’ll drive over by car… tight squeeze…”

Unnoticed by the others, Tynan had been listening to Marks with growing horror, and now the Englishman leapt to his feet and began shouting. According to Plimpton, the red-faced theater critic squinted his eyes and flapped his arms like an enormous bird while denouncing Marks. He didn’t want to be in the same room as an executioner, Tynan gasped, let alone witness his handiwork. He would attend the execution only to run in front of the firing squad to protect the condemned. Tynan then stormed out of the bar, followed by Dundy.

“What the hell was that?” asked Marks. He told the remaining writers to meet him in the lobby of a nearby hotel at 8 p.m.

With a Colt .45 revolver, $400 in cash, and “about ten words in Spanish,” as he later put it, Marks took a boat to Cuba. His plan was as audacious as it was simple: He would join the revolution.

Almost nothing about Herman Marks’s early life suggested that he would someday play a pivotal role in a Latin American revolution. He was born in Milwaukee in 1921, and raised in a neighborhood of shoddy brick houses and bare streets. His father, Frederick, was an unemployed alcoholic who beat him; his mother, Martha Yelich, barely kept the family afloat by working as a short-order cook in a diner. He does not appear to have been close with his elder sister, Elsie, or his younger one, Dorothy; but he remained devoted to his mother throughout his life, in his own eccentric fashion.

The Markses’ volatile marriage crumbled during the Great Depression, when Herman was 12. After his mother remarried, Herman began getting into trouble. He skipped classes and was expelled from every school he attended; at 14, he was sent to a reformatory, where he ran away on three occasions and was once caught stealing a car. Over the next two decades, he was arrested 32 times in ten states, from Hawaii to Maine, mostly for drunkenness, petty theft, and disorderly conduct.

He never stayed more than three months in any one place, working odd jobs in factories, on docks, and at horse ranches. In April 1939, he joined the merchant marine, and he served in the Pacific during World War II. (He later claimed in court that he “had been in jails all over” the region, including while on shore leave in Australia.) After the war, Marks floated aimlessly around the United States, Mexico, and Canada, adding to his rap sheet: vagrancy in Texas, public drunkenness in Ohio and North Dakota, attempted grand larceny in New York City, and “prowling” in Las Vegas, a crime for which he was given 30 days in jail and then told to leave town. In Los Angeles in 1949, he robbed an elderly woman, drunkenly grabbing her by the throat. According to the police report, he only made away with naphthalene mothballs “to the value of 29 cents.” He got six months for assault but escaped from jail with two friends. While fleeing, all three seriously hurt their ankles after jumping from a dangerous height; Marks and one of the other men limped on for weeks, until they were caught in Galveston, Texas, and sent back to California to finish their sentences.

Back home in Milwaukee, at age 27, Marks brawled with his mother’s third husband and physically threw him out of the house. (Yelich took her son’s side; he was fined five dollars by local authorities for his actions.) Later that same year, he was arrested and convicted of carnal knowledge with a 16-year-old girl. According to the police report, Marks was working as a stable hand and met the girl at a bar, where, the police conceded, she had shown the bartender a birth certificate that said she was an adult. The pair then attended a riotous celebration in a barn where, an investigator noted, “drinking and sex parties went on almost nightly.” Marks was sentenced to three and a half years in prison.

His niece, Penlo Hobbs, remembered her relatives being frightened of Uncle Herman well before he entered the state penitentiary in Waupun. “He was the bogeyman,” she said. “We weren’t allowed to have anything to do with him.” Even Marks’s mother had reservations about her son. “I don’t know what happened to him,” she once told the Milwaukee Sentinel. “Whatever he did was not my fault. I sent him to parochial school and raised him good.”

She said Marks was generous when he wasn’t broke, lavishing her with bouquets of flowers, but mainly he spent his money on girls and booze. And he had an explosive temper. “He was always drinking and fighting,” his mother said. “As soon as somebody said anything wrong, he was up and mad.” Marks’s erratic personality was symbolized by his tattoos. His left arm bore a double heart inscribed with the words “Love, Nellie.” (There is no record of who Nellie was.) On his right arm was a skull pierced with a dagger, alongside the military motto “Death Before Dishonor.”

His mother took Marks in after he was released from Waupun penitentiary in 1955. A few months later he left home again. “He kissed me one day and said he was going,” his mother recalled. Somebody took a photo of him looking bronzed and fit, which Yelich carried in her purse until the day she died. “I don’t think he knew where he was going,” she said. “He was looking for something.”

He found it on a shrimp boat in Florida. While hauling nets in late 1957, he ran into some men he knew from his days in the merchant marine. They were from Cuba, an island Marks had visited several times in the service, and once as a tourist. It was now embroiled in a civil war between leftist revolutionary guerrillas, led by a young lawyer named Fidel Castro, and the military dictatorship of Fulgencio Batista. That Christmas, Marks learned that one of his Cuban friends had been murdered in Havana by military police; they purportedly broke into the man’s house one night and shot him dead at his kitchen table. Soon after hearing the news, Marks went to an army surplus store in Key West and bought olive drab fatigues and paratrooper boots. With a Colt .45 revolver, $400 in cash, and “about ten words in Spanish,” as he later put it, Marks took a boat to Cuba. His plan was as audacious as it was simple: He would join the revolution.

Havana was under military curfew, with Batista’s menacing, blue-uniformed intelligence officers patrolling the streets. Loitering in the city’s bars, Marks failed to find any agents of M-26-7, Castro’s underground 26th of July Movement, named for the date of the group’s first armed uprising. So Marks took a bus east to the sleepy town of Manzanillo, in the tropical foothills of the Sierra Maestra, where he met two young Cubans also hoping to join the guerrillas. The trio hiked for three nights before reaching a jungle outpost of some 40 rebels under the command of Captain Paco Cabrera. An English-speaking officer interrogated Marks. Like many of the roughly two dozen yanquis who ultimately joined Cuba’s rebellion, Marks rewrote his personal history. According to one guerrilla, he claimed that he was a Korean War veteran; to others, he explained that his facility with weapons was born of a childhood enthusiasm for guns. He was accepted into the group with a meal of beef and celebratory rum.

Marks’s profile among the guerrillas rose when he saw three teenagers fumbling with a U.S. Army .30-caliber machine gun and stepped in to show them how to disassemble and clean it. By the time he was finished, a crowd had gathered around him, with men holding up rusted and broken weapons, wordlessly appealing for help. He was soon tasked with fixing the array of firearms used by rebel forces, everything from sport rifles to shotguns to carbines dating back to Cuba’s colonial days.

Marks was assigned to the unit led by Che Guevara, which suffered the highest casualties in the rebel army—one of its cohorts was dubbed the suicide squad. Marks quickly rose through the ranks to become a captain. In the spring of 1958, Che transferred him to Minas del Frío, a rebel stronghold, where Marks helped establish a military school and train recruits to repel the impending Operation Finish Fidel, a mass invasion of the Sierra Maestra by Batista’s army, which outnumbered the guerrillas 100 to 1. By May, Marks was on the front lines of combat. In one skirmish, he broke three teeth on a rock when he tripped leading a charge; in another, he led a group of 18 rebels who disabled a 250-man convoy in an ambush.

By August, Batista’s generals had to admit that they could not dislodge the guerrillas, and the army withdrew from the Sierra Maestra. The following month, Marks volunteered to join Che on a harrowing 350-mile mission across the mosquito-filled swamps of the eastern lowlands. The rebels hoped to establish a new base in the Escambray Mountains of central Cuba and use it to seize enough ground to effectively cut the island in half. In a biography of Castro, journalist Tad Szulc observed that the expedition, where the men would abandon the known terrain of the Sierra to trudge across exposed, unknown, and hostile territory, “must have seemed like a demented plan.” Che warned volunteers that conditions would be miserable, food short, and casualties likely close to 50 percent. Marks signed up anyway.

Although most of the mission’s men survived the trek, it was universally agreed to be the most grueling campaign of the entire war. Che’s column walked mostly at night to avoid army patrols and strafing airplanes. They forded rivers naked and once traversed a shallow lagoon filled with razor-sharp plants. They suffered from dire hunger and endured hurricane-fueled rain. “I’ve been through enough mud and water to last me the rest of my life,” Che wrote to Castro. “Hunger, thirst, weariness, the feeling of impotence against the enemy forces that were increasingly closing in on us, and above all, the terrible foot disease that the peasants called mazamorra—which turned each step our soldiers took into an intolerable torment—had made us an army of shadows.”

During a skirmish, Marks was wounded in the knee and ankle. Infection set in. “Pus and blood was continuously running, and I couldn’t get a shoe on my foot,” he later said. He had trudged with Che for over a month to get to the Escambray Mountains, but the possibility of fatal gangrene now threatened. Che decided to get the yanqui to safety. In early November, supporters of M-26-7 smuggled Marks from a farm into the city of Santa Clara, where he was dispatched by plane to Key West for medical care.

Although he had gone to great lengths to make sure Marks did not succumb to his injury, privately Che was not unhappy to see him go, writing in his war journal that the American “fundamentally … didn’t fit into the troop.” One of Che’s close aides, Enrique Acevedo, told biographer Jon Lee Anderson that Marks was “brave and crazy in combat, tyrannical and arbitrary in the peace of camp.” According to Acevedo, the American’s ruthless nature had disturbed the Cuban recruits—particularly his readiness to volunteer for execution duty, which he did with “an enthusiasm that was unseemly.”

The Cubans’ reaction to Marks echoed that of a reform-school psychiatrist who’d encountered him when he was 16. The psychiatrist reported that Marks was oddly detached—“a very stolid emotionless person when not excited” who “shows almost a lack of adequate feeling in respect to situations he finds himself in.” Later, when Marks was in Waupun prison, the facility’s psychiatrist found that he was “amoral rather than immoral,” and was “narcissistic in his makeup.”

These assessments would resonate throughout Marks’s peculiar career in Cuba.

Part Two

On New Year’s Day in 1959, Marks was resting in his hospital bed in Key West, listening to the radio, when a news update came over the airwaves: Batista had escaped from Havana in the hours before dawn that day, abandoning his country. In that moment, Castro’s rebel army had been handed effective control of Cuba. Days later, Marks hobbled to the docks and took the first ferry to Havana, which was still operating daily. He wanted to savor the victory, rejoin his compañeros, and, not incidentally, claim his promised share of property following the revolution’s land reform, which had always been at the top of Castro’s agenda.

Marks arrived in Havana on January 3 to find the city in a tense state of limbo, awaiting Castro’s arrival in a triumphant procession from the east. When news of Batista’s flight had filtered out on New Year’s Day, jubilant Habaneros sacked several casinos and smashed parking meters with baseball bats; Marks walked from the dock to the presidential palace along empty streets strewn with debris and shattered slot machines. Most of the city was under lockdown, with gun-toting cadres loyal to the M-26-7 maintaining a fragile order. Batista’s disgraced police and rank-and-file soldiers were all lying low; Boy Scouts had taken over as traffic cops, directing the few cars still on the roads.

At the presidential palace, armed student activists told Marks that his old comandante, Che, and an advance guard of 200 rebels had taken over La Cabaña. The golden-hued Spanish fortress was built in the age of conquistadors to guard galleons filled with Aztec and Incan gold from pirates; under Batista it had been a military base and a prison. It housed some 3,000 troops, but the demoralized officers had surrendered to the rebels without firing a shot. Marks made his way there to report for duty. 

He spent his first night in Che’s billet, carousing, and after breakfast the next morning, Che took him to the quartermaster to find fatigues and a beret. Whatever concerns Che had had about the American during the rebels’ trek eastward the previous year weren’t enough to dissuade him from appointing Marks head of security at La Cabaña.

On January 8, Havana’s silence broke when Castro arrived, riding atop a tank and surrounded by guerrillas. He proceeded along the Malecón waterfront, thronged by adoring crowds. Eventually, Castro took the penthouse apartment atop the Havana Hilton as his temporary office, while guerrillas slept on the floor of the hotel foyer. For weeks the streets of Havana were filled with music and dancing to celebrate the demise of the ancien régime. Guerillas were offered free bus rides, meals, and alcohol wherever they went.

At La Cabaña, to focus his officers’ restless energies, Che offered literacy classes and crash courses on international politics, explaining the importance of Vladimir Lenin and the Soviet Union. Still, a festive air permeated everything. Che’s office was besieged by female admirers who lined up for hours hoping to see him; when he barred the door, they climbed through the windows. The fortress’s former officers club was thrown open to the barbudos—“bearded ones,” as the shaggy young guerrillas were nicknamed. The English writer Norman Lewis visited La Cabaña and found rebels in freshly pressed uniforms, “sipping delicately from small coffee cups, and smilingly discussing the past achievements and future promise of the new order.”

Lewis was among the small army of foreign artists, writers, and celebrities who descended on Havana to enjoy the intoxicating “honeymoon of the revolution,” as the French intellectual Jean-Paul Sartre called it. Another was veteran Milwaukee Journal reporter William J. Normyle. He visited Havana in mid-February, and was surprised to learn that Castro’s guerrillas included one of Wisconsin’s native sons. He wrote a glowing profile of Marks, dwelling on his idealism and derring-do as a freedom fighter. Marks revealed that he had no plans to leave Cuba anytime soon. “I’m staying here,” he told Normyle. “There’s a lot of work to be done.”

Marks, it seems, conveniently left his criminal history out of his interviews, telling Normyle that he had attended vocational school in Milwaukee before joining the merchant marine. What’s more, Normyle’s article didn’t mention that at least part of Marks’s work in Cuba was shooting prisoners to death.

Three judges heard attorneys and witnesses, and parsed the evidence to decide who was mistakenly charged, who deserved long prison sentences, and who should be sent al paredón—“to the wall.”

For many foreigners, the first dark chord in Havana’s celebratory mood was struck by the start of trials for “war criminals” from the Batista regime. Nobody knows the exact death toll of the seven years of Batista’s military rule. The figure 20,000 was offered by the director of Havana’s morgue in 1959, and accepted by the revolutionary government. Although the true number may be less, nobody disputes that the carnage was horrific. Nearly every Cuban had a family member who was illegally detained, tortured, murdered, or disappeared by the regime. Castro urged Cubans not to take revenge against Batista’s henchmen who remained on the island after the dictator’s escape. He promised proper trials based on laws he had signed in the Sierra Maestra in February 1958. Yes, his brother Raúl had ordered that more than 70 Batista loyalists be machine-gunned before open graves in the city of Santiago, but henceforth, Castro insisted, the proceedings would be civilized—there would be none of the bloody mob violence associated around the world with uprisings and revolutions past.

The first trials, the so-called Cleansing Commission, were set up in Havana in January 1959 under the supervision of a young lawyer named Miguel Ángel Duque de Estrada. Che presided as the “supreme prosecutor.” Targeting the most detested members of the Batista regime, the trials were held at La Cabaña, where 800 prisoners were squeezed into stone cells made to hold only 300. Three judges heard attorneys and witnesses, then parsed the evidence to decide who was mistakenly charged, who deserved a long prison sentence, and who should be sent al paredón—“to the wall.” By the end of January, some 100 Batista loyalists had been executed.

Marks was in many ways the perfect soldier to run the firing squads. He was ambitious and had shown in the Sierra that he was not averse to undesirable and even grisly tasks. He believed that the executions of Batista’s most loathsome minions was part and parcel of the revolution, and he saw Che’s decision to put him in charge of carrying out such a difficult job on behalf of the Cuban people as an honor.

Marks achieved a burst of notoriety when the new government initiated Operation Truth. It chose three of the most brutal Batista partisans to prosecute at a public trial, and Castro invited international journalists as observers. He even offered to pay their expenses. All told, 385 journalists from U.S. and Latin American media converged on Havana. It turned out to be a PR misstep; what happened next was a show trial, held at the aptly named Coliseum, the national sports stadium. The accused men were paraded before 18,000 jeering and furious Cuban spectators. For the benefit of those who could not attend, the event was televised live.

The first accused man to take the stand was Major Jesús Sosa Blanco, a garrison officer from the provincial town of Holguín, who was charged with 108 murders, many preceded by savage torture. He was also believed to have ordered the massacre of unarmed campesinos. Over 12 hours, some 40 tearful witnesses, including widows and a 12-year-old boy, took the stage to testify about the murders of their loved ones. The audience screamed and wailed. When the handcuffed defendant morosely repeated that he had only done his duty, his words were drowned out by the crowd chanting, “Al paredón! Al paredón!”

Sosa Blanco was convicted and sentenced to death. On February 18, his appeal was adjudicated without a public audience, and his sentence was upheld. Some 200 barbudos came to watch him die. The condemned man was transported in a small bus to La Cabaña’s dry, floodlit moat, where Marks unlocked his handcuffs and led him to the spot where he would be executed. According to Marks, Sosa Blanco asked if he could address the crowd with some final words and then give the orders to the firing squad himself. Marks agreed. “Although I am marked as a criminal,” Sosa Blanco said, “I have served my government to the best of my ability as an officer.” He wished good luck to all those gathered, and then cried out: “Pelotón, atención! Prepare! Apunte! Fuego!”

All this left the international community outraged. U.S. journalists in particular denounced the executions as well as the trials at the Coliseum, some of which were televised, with language that veered into ugly bias. Time led the charge, decrying the “popcorn-munching atmosphere” and insisting that it revealed a congenital Cuban longing for “blood purges.” U.S. senators held press conferences to warn that the Cuban uprising was spinning out of control, just as the French, Russian, and Chinese revolutions had before it.

Many Cubans saw American objections to the executions as rank hypocrisy. For seven agonizing years, the U.S. government had not breathed a word of protest against Batista’s regime, which had killed so many Cuban citizens. After Batista’s flight, mass graves were opened all over the island, full of corpses with broken limbs or missing eyes; many victims had been burned, strangled, disemboweled, or buried alive. Police stations were found to contain torture implements, including handmade tools designed for pulling nails and teeth, electrical wires that could be inserted into ears, and “fire seats”—perforated metal thrones under which flames mutilated genitalia. When Castro asked Cubans for a show of support for Operation Truth, a million demonstrators gathered in Havana to demand more executions and to express outrage at the Americans’ double standards.

Soon, though, with a diplomatic tour to the United States pending, Castro bowed to international pressure and moved the trials back behind the closed doors of La Cabaña. They were now held at night within the bowels of the prison, “in a large hall that might have served as a church,” according to Norman Lewis. Benches held dozens of prisoners’ relatives, many of them women and children. “The place was surprisingly quiet,” Lewis noted, “and despite the provision of microphones I had to listen intently to follow the details of what was going on, especially when prisoners under examination replied to questions, as they usually did, in a low-voiced, hesitant fashion. Two small birds fluttered continuously under the roof.”

Although the accused men Lewis saw tried were “criminal small-fry,” he flinched at the barbarity revealed in their testimony. A boyish 18-year-old named José Cano was accused of stabbing one victim in the eyes before murdering him. Another, Gregorio Gonzalez, aged 22, said he had executed a 73-year-old grandmother with two shots to the head for harboring a pair of rebel agents in her house. A death sentence was handed down for both men. Only a woman’s gasp broke the silence in the room.

A photograph taken around the time, published in The New York Times Magazine, shows Marks in smart guerrilla khakis, standing at attention as he hears a verdict. It was his job to escort men like Cano and Gonzalez to their deaths, one after the other.

Visiting reporters, politicians, and movie stars lined up for their turn to witness an execution, including the Hollywood matinee idol Errol Flynn, who was so shaken by the experience that he retched on a guard’s shoes.

By the end of March 1959, the nightly firing squads at La Cabaña had become something of a production line. According to wire reports, Marks had already carried out 200 executions, though he claimed the figure was closer to 80; on one busy night, he told an Associated Press reporter, 11 men were put to death. To the many foreign journalists who attended, Marks insisted that he was acting as a humanitarian. It was he who had suggested that the executions take place in the moat beneath the looming white statue of Christ, because the figure would be an uplifting last sight for the condemned. He said he also wanted to ensure that the process was clean and efficient, compared with messy executions that had been conducted in the provinces.

Some observers found the proceedings a little too efficient. “It was a mechanical, cold-blooded, business-like procedure for Marks,” New York Times reporter Herbert Matthews wrote, “like a butcher killing cattle in an abattoir.” Still, glitches happened. When the floodlights failed, sentences were carried out by the headlamps of military Jeeps, as if they were gangland murders in Hollywood B movies. There were scenes of panic and despair. Some condemned men tried to buy their freedom with money or gifts. A more serious problem was that the young soldiers in the firing squads, who were generally between 16 and 20, often lost their nerve at the decisive moment. The Cubans did not follow the European tradition of giving one of the riflemen a blank round to salve the squad’s consciences, so the soldiers often aimed for a leg, a shoulder, or the wall. This left Marks to fire the fatal shot into a man now writhing in agony. On one occasion, when a man waved a Santeria hex at the riflemen and cursed them, their children, and their grandchildren, all six deliberately missed. Marks shot the man himself and had the squad court-martialed.

Marks’s local infamy rose another notch when the English-language Times of Havana, beloved by American tourists and expats, ran a profile of him on April 2. It was largely sympathetic, apart from describing him as “humorless” and noting that he “discusses his duties unsmilingly and unemotionally.” Marks hit on many of the themes he would return to in interviews over the coming months. “Running firing squads is not a pleasant job, but it’s one that must be done,” he said. “When a soldier gets his orders, he carries them out whether he likes it or not.” Marks also expressed his love for his new home. “Cuba is a beautiful country,” he said. “The people are wonderful. I like everybody here and most everybody likes me. I’ve got a good position in a happy, contented place.”

A long waiting list formed for Marks’s macabre tourist attraction. Visiting reporters, politicians, and movie stars were eager for their turn, including the Hollywood matinee idol Errol Flynn, who was so shaken by the experience that he retched on a guard’s shoes. Still, Flynn was fascinated enough to invite Marks to dine with him and his 16-year-old paramour, Beverly Aadland, in his hotel suite, where Flynn argued that condemned men should have a say in the method of their own executions. Marks disagreed, pointing out that they had never given their victims a choice. “Somebody was pretty smart in the government by putting an American in charge of blowing out Cuban brains,” Flynn wrote in a letter at the time. (Flynn also reported the rumor of Marks’s sadist coup de grâce—that he deliberately disfigured some condemned prisoners by emptying his pistol into their heads—but admitted that he had not seen it himself, despite attending several executions. The story, Flynn wrote, was “hearsay.”)

Ernest Hemingway encouraged George Plimpton to witness an execution, because “it was important that a writer get around to see just about anything, especially the excesses of human behavior.” But Plimpton didn’t attend on the night he first met Marks at El Floridita. When he, Tennessee Williams, and the other foreigners whom Marks had invited convened at the appointed time in the hotel lobby, Marks turned up only to inform them that the evening’s executions had been called off. Plimpton speculated that Marks had been set on edge by Kenneth Tynan’s rant about the proceedings at La Cabaña, and that he sensed others in the group might have concerns. “He had doubtless concluded that we were an odd lot: our own doubts so obviously seethed; we didn’t seem grateful; we kept staring at him with our mouths ajar,” Plimpton wrote.

It is also possible that Marks had no idea how famous Williams was when he extended the invitation, and had been subsequently warned off by a superior. Only the afternoon before, Tynan and Williams had visited the presidential palace to meet Castro. They waited for two and a half hours until, Tynan later wrote, “with a shrug and a cry, someone identified Mr. Williams as the famous Yankee playwright, and we were promptly whisked into Castro’s sanctum, where, unknown to us, a crucial cabinet meeting had been in session.” Castro halted the proceedings to pay tribute to Williams, explaining in faltering English “how much he admired his plays, especially the one about the cat that was upon the burning roof.”

But things didn’t end in the hotel lobby. In a final twist, as Plimpton revealed many years later to James Scott Linville and another colleague at The Paris Review, Hemingway himself decided to take his friend on an evening jaunt to see Marks at work. He prepared shakers of cocktails for himself and Plimpton to take with them. According to Linville, “Arriving at their destination, they got out, set up chairs, brought out the drinks, and arranged themselves as if they were going to watch the sunset. Soon enough, a truck came. … The truck stopped and some men with guns got out of it. In back were a couple of dozen others who were tied up. Prisoners. The men with guns hustled the others out of the back of the truck and lined them up. And then they shot them. They put the bodies back in the truck and drove off.”

By then, Marks’s reputation as a killer was international news. An AP reporter named Theodore A. Ediger broke the story in late March, and his work was syndicated, appearing in newspapers across America, including the Milwaukee Journal. Ediger’s profile detailed Marks’s work as an executioner, but the author was nonetheless a little starstruck. He described Marks as a “slender, sun-bronzed officer” who was fondly referred to as “El Capitán Herman” by his Cuban comrades. When asked about his youth in America, Marks claimed to have worked as a coal miner in Butte, Montana, and as a “hospital surgeon attendant.” Ediger concluded the piece, “He says he likes Cuba so much that he is not homesick.”

This time the publicity in Milwaukee, where Marks’s photo ran on the front page, drew the attention of John C. Burke, the warden at Waupun penitentiary, where Marks had done time. Burke contacted the Journal, and Normyle, the reporter who had met Marks in Havana back in February, did some digging and discovered Marks’s 32 criminal convictions. “Marks Left Crime Trail,” another front-page headline soon read. In the accompanying article, Burke described Marks as “a real stinker” and a “rascal” who caused constant trouble in the prison by refusing to work. The exposé was picked up by other papers and various magazines, including Time and Newsweek. It also heralded Marks’s debut in The New York Times, under the headline “Executioner Is Ex-Convict.” Marks’s criminal past was linked to rumors of his cruelty in Cuba, and to his nickname, El Carnicero.

If anything, the coverage enhanced Marks’s mystique in Havana’s expat circles, where oddballs and outsiders abounded. Marks was given the best tables in the swank restaurants that were still operating in the city’s Art Deco hotels. He became a familiar figure at El Floridita and Sloppy Joe’s, another popular drinking establishment. He made regular cameos at an office in downtown Havana, which was shared by New York Times correspondent Ruby Hart Phillips—a prim, matronly figure whose uniform was “grey sweater, carmine blouse and blue slacks,” according to Time—and Ted Scott, the brothel-hopping Times of Havana editor. In his office, Scott had set up a makeshift shooting gallery, with cards that moved on a wire; in his downtime he used an air pistol for target practice. One day, Phillips had to restrain Marks from trying to hit the cards with his .45 revolver.

Jean Secon, a striking American photojournalist in her twenties, had moved to Havana in 1958 and established herself as a stringer. She was arrested by Batista’s regime for attempting to meet Castro in the Sierra and flown back to Havana. After the revolution succeeded, she became a fixture in the city, hobnobbing with barbudos in restaurants and bars. In early 1959, she met Marks while attending an execution. The two hit it off and became romantically involved.

The couple shared a talent for Gatsby-like reinvention. Like Marks, Secon had buried her past in America. She’d fled her life in upstate New York, divorced her husband, and worked as a model in Manhattan before lighting out for Cuba. Now her life was full of adventure. Her future in the tropics, and with Marks, looked bright.

Part Three

In May 1959, following a successful diplomatic tour of the United States—where he was feted by crowds in Washington, D.C., and New York City, and on the campuses of Harvard and Princeton—Castro put an end to the execution of “war criminals.” According to the most reliable figures, some 500 of Batista’s cronies had been sent to the wall, most of them on Marks’s watch. On June 2, Che was married at La Cabaña to his sweetheart Aleida March, a guerrillera who had been his personal assistant during the war. After a rum-fueled reception in his bodyguard’s quarters, Che was sent by Castro on an international tour, which took him to India, China, and Africa.

Marks and the other men under Che’s command regarded his new diplomatic role as a demotion from his work at La Cabaña. They were also upset to learn that they would all be transferred to the sleepy province of Las Villas to do odd jobs, such as enforce the desegregation of beaches. “It was like the house falling down,” one of Che’s young officers recalled.

Over the summer of 1959, the happy atmosphere for American expats in Cuba eroded. Castro’s government followed through on its promise to break up sugar estates larger than 3,300 acres, including Castro’s own family farm near Birán and vast tracts owned by American companies. Instead of providing compensation in cash, the government offered dubious bonds. Tit-for-tat retaliation between Washington and Havana ensued. Moscow, sensing an opportunity, stepped up its support for Castro’s government. Historians continue to debate whether Castro jumped or was pushed into the arms of the Soviet Union. What’s certain is that his government gradually filled with Communist activists.

Marks would later tell U.S. authorities—perhaps playing to their sentiments—that he opposed the creep of Communism into the ranks of Cuba’s freedom fighters. He claimed that when he discovered that the literacy teachers at La Cabaña were using Communist pamphlets for their classes, he made a bonfire out of the reading material—a move that surely would have annoyed the pro-Soviet Che, had he heard about it, but which was not yet a punishable offense. After the move to Las Villas, Marks blamed his political outspokenness for a series of further transfers deeper into the countryside, a sort of Cuban Siberia. For a while he was in a “no-man’s-land,” as he put it, training “misfits” from the rebel army who had gone AWOL or fallen asleep on duty. Eventually, he ended up in the city of Santa Clara, with his captain’s rank intact but no duties to perform.

While he was posted in the provinces, Marks observed from a distance a bizarre episode of Cold War espionage in which a fellow American guerrilla fighter—William Morgan, known as the Yankee Comandante—helped foil a military coup against Castro backed by the right-wing dictator of the Dominican Republic. In the crackdown on critics of the revolution that followed, Secon made her first appearance in The New York Times, not as a reporter but as a news item. When she and another journalist tried to interview Morgan in his Havana home, the pair had the honor of being the first U.S. correspondents arrested by the Castro regime. The nature of the charges was never clear, a sign of the government’s increasingly authoritarian bent and Castro’s suspicion of a free press. Secon and the other journalist were detained for a week, then released.

In September, Che returned from his triumphant world tour—he was the toast of the international left—and revisited his old regiment in the provinces, informing them that he was moving into Cuba’s civil sector. He would run the Industrialization Department, to develop the national economy, and take over as head of the National Bank. Marks, though, remained in his rural limbo; Che, always a calculating figure, had evidently decided that the American was no longer of any special use. Then, in a lucky break, Marks ran into another of his former guerrilla commanders, the prodigiously bearded Camilo Cienfuegos, who pulled a few strings and got him transferred back to Havana to command an infantry battalion at Campo Libertad (Fort Freedom). Marks was put in charge of the various security details assigned to officials’ homes and to Havana’s railways and bridges. He was given a large house with a swimming pool, along with a Packard sedan.

That October, one of Castro’s most beloved Sierra compañeros, Huber Matos, resigned from the rebel army to protest the growing influence of Communists in the government. He was immediately arrested as a counter-revolutionary and sentenced to 30 years in prison. Matos’s imprisonment was a turning point in U.S.-Cuban relations: The Eisenhower administration issued increasingly bellicose statements, and Cubans began to feel a sense of siege. Bombs planted by anti-Castro agents exploded in Havana stores, and light planes from Florida dropped incendiary devices to set fire to sugarcane fields. Anti-Castro guerrillas began operating in the countryside, funded by right-wing exile communities in Miami. By the end of 1959, the CIA was thinking about assassinating Castro, a consideration supposedly justified by the increasing presence of Soviet officials in Cuba. The American public was also souring on the revolution. It wasn’t long before the New York press, which previously had compared Castro to George Washington, began referring to the Cuban leader contemptuously as El Beardo.

As rumors of an impending U.S. invasion grew, Castro began arming Cuban citizens with vintage Soviet weapons, and he revived the tribunals—this time with the power to impose a death sentence for offenses against the revolution. In January 1960, Marks was made chief security officer at El Princípe prison, another colonial relic in Havana. Its cells were crammed with 3,000 inmates, mostly opponents of Castro from militant dissident groups. The Butcher was told to get back to business.

“I am proud to have fought with such men as Che Guevara and Fidel Castro, proud to be part of the revolution,” Marks concluded, “but I am also proud of being an American citizen, and I do not intend to stop being one!”

In February 1960, a U.S. embassy staff officer named Wayne Gilchrist steered his lumbering Chevrolet into the cobbled courtyard of El Princípe and handed Marks an envelope. Inside was a Certificate of Loss of Nationality. The United States had stripped Marks of his citizenship.

It was another indicator, if any more were needed, that the romance between the United States and revolutionary Cuba was well and truly over. One by one, Marks and other yanqui expats who had remained in Castro’s forces after Batista’s exit were stripped of citizenship. Their crime? Serving in a foreign military.

Marks did not take the news lying down. A few days after Gilchrist’s visit, he held a press conference. Secon covered the thinly attended event—Marks later conceded that it had lured only “three or four” journalists—for the Times of Havana and the wire service United Press International. The Times ran her story on the front page, with a photo of Marks wearing a beret and a “well-trimmed beard,” as she described it, which he “thoughtfully fingered” as he pondered his legal situation. Marks claimed that Americans in Cuba were being targeted for political reasons. “A person’s citizenship is his right of birth,” he declared, noting that Americans had fought in the Spanish Civil War and as part of the British and French armies in the two World Wars without losing their nationality. “I am proud to have fought with such men as Che Guevara and Fidel Castro, proud to be part of the revolution,” he concluded, “but I am also proud of being an American citizen, and I do not intend to stop being one.”

Secon editorialized her own outrage. “If the reputation Herman Marks won in the Sierra Maestra still holds,” she wrote, “the U.S. State Department will have one hell of a battle denying what the man calls his birthright.”

By the time of the press conference, Marks was well into his stint at El Princípe. His time there produced a string of lurid stories, although their veracity is difficult to establish; most were retroactively spread by Miami Cubans when anti-Castro propaganda became virulent in their city. In the Cuban poet Armando Valladares’s error-filled 1986 memoir, Against All Hope, Marks is depicted as a savage drunkard who referred to the prison as his “private hunting preserve” and would order the guards to attack inmates with chains and truncheons before stealing their possessions. Valladares describes Marks’s executions as gory ordeals, with the American often bringing his pet dog with him to lap up the blood of the condemned. John Martino—an American casino worker with mob connections who was arrested for smuggling Batista henchmen out of the country—wrote a tome in 1963 called I Was Castro’s Prisoner, which includes a chapter entitled “Sadists and Perverts of El Princípe.” After one inmate begged to be spared, Martino claimed, Marks fired all the rounds in his pistol into the man’s face, turning it into “a shapeless piece of meat,” and supposedly giving his mother a fatal heart attack when she opened his coffin at the funeral.

The story later circulated that Marks was stripped of his position at El Princípe due to his brutality and alleged theft of prison funds; Marks denied the charges when they surfaced. Whatever the truth, he was transferred from the prison in March 1960 to downtown Havana, where he trained police officers in firearm safety after a series of clumsy shooting accidents injured bystanders. It was a demotion, perhaps, but hardly a disgrace.

Despite months of relative luxury thanks to his job perks, Marks was painfully aware that life for Americans in Cuba was becoming more dangerous by the day. The escalating drama was excellent copy for Secon, but it risked spinning out of control and trapping the couple, or worse. The most alarming sign was an enormous May Day rally in the Plaza de la Revolución, where cadres of Cubans armed with their Soviet weapons marched past Castro’s podium in a tropical echo of Moscow’s military parades. Castro orated about the threat of a U.S. invasion, which Cubans, he said, would face like the Spartans at Thermopylae. A chant began: “Cuba sí, yanqui no!”

Marks became convinced that he was being followed by Cuban intelligence agents. His paranoia increased when, in early May, several officers close to him were arrested. Secon was just as jittery. As Marks later recounted, “A lot of people were coming to the same conclusion: Get out while there was still a chance.”