WHEN CHE HAD first approached the Escambray mountains in October, he decided to dismiss his most unpleasant recruit, the American Herman Marks. A native of Milwaukee, with the chinless, paunchy look of a suburban accountant before he grew the regulation beard, Marks had made his way to the Sierra Maestra six months earlier and offered his services as a supposed Korean War veteran. His presence was first mentioned by Raúl, who told Fidel in a letter on March 9, 1958, that he had been joined by a mysterious, twenty-six-year-old gringo—“He’s brave in battle and gives military training to the chicos.” Marks helped the men make Sputnik grenade-throwers and showed them how to use a car battery as a bomb detonator. It would later be discovered that Marks’s war record was a complete fabrication. In fact, he was a draft dodger who had been arrested thirty-two times in the United States for crimes including armed robbery, theft, and statutory rape. His affinity for firearms had been developed while staging heists.
Nobody in the Rebel Army was prying. Marks transferred to Che’s column during the summer offensive and acquitted himself so well that he was promoted to captain. It was only when he joined Che’s autumn expedition across the island that his true nature began to come out. At the end of the ordeal, Marks was one of eight men Che asked to leave “in an attempt to clean out the scum of the column.” He had been wounded in the foot and fallen sick, Che reported to Fidel, but the real reason was that he “fundamentally didn’t fit into the group.” Another guerrilla, Enrique Acevado, explained that Marks was “brave and crazy in combat, tyrannical and arbitrary in the peace of camp.” Evidently his fondness for conducting executions—particularly the coup de grâce—bordered on the sadistic and disturbed other men.
By then, Marks was less of an exotic figure; American soldiers of fortune were floating all across Cuba. Only days after Che dismissed the perverse Marks, he encountered an even more surprising gringo soldier in the depths of the Escambray Mountains: William Morgan from Toledo, Ohio, who would soon become internationally renowned as Fidel’s “Yankee comandante.”
AMERICANS WERE FASCINATED by stories of their own countrymen joining the guerrillas. According to US embassy estimates, there were some twenty-five young gringos bearing arms against Batista by late 1958. These would-be Lafayettes were an oddball bunch. Some, like the hardened Marks, are difficult to romanticize. But many others were genuine free spirits who longed to escape the leaden conformity of Cold War America. Cracks were already beginning to appear in the facade of suburban prosperity: Allen Ginsberg’s Howl had been published the month before the Granma landing in 1956, Jack Kerouac’s On the Road came out in September 1957 and became an overnight bestseller. At the same time, Martin Luther King, Jr. organized the Montgomery bus boycott in Alabama. The bearded Cubans tapped into the amorphous dissatisfaction many young Americans felt with society; “the sixties,” in a sense, were gestating in the late 1950s.
In mid-1957, after the three teenage runaways from Guantánamo Bay had their fifteen minutes of fame on CBS TV, a string of others developed addled plans to emulate them. (We know, for example, that a dozen UCLA students plotted to take jeeps via Key West to the Oriente.) But while the Gitmo boys became minor celebrities, most yanqui volunteers are today ghostly figures whose adventures must be pieced together from stray references. Some remain entirely anonymous. Raúl mentions a gringo “demolitions expert” with echoes of Hemingway’s Robert Jordan; Times correspondent Ruby Hart Phillips met “a boy from Iowa” with Fidel in the summer of 1957; Life refers to an ashen-faced Chicagoan with polio who worked as a guard. Not all potential American volunteers were successful at reaching their goal. A Miami pipe fitter named Bill Leonard was reported walking into a Cuban police station in Oriente and asking for a “pass” to the Sierra Maestra so he could visit “his friend Chuck Ryan” who was fighting with Fidel. The astonished officers searched him, found a knife and tear gas gun, and—after letting him cool his heels in the cells—put him on a train back to Havana.
Many Americans who did make it into the mountains buckled under the hardship of guerrilla life. During the hostage crisis, journalists had met Charlie Bartlett, the Navy machinist’s mate from California, who had joined Raúl after seeing Batista’s soldiers beat up civilians. A few months later, Bartlett slipped back to the Navy base and was court-martialed. Even more feckless was Edward Bethune, a soldier of fortune from Knoxville, Tennessee, who hiked up to the Comandancia and was inducted into the Rebel Army, but left after only a few days complaining he had a “toothache.” (Perhaps he couldn’t face the pedal-operated dentist’s chair.)
Other yanqui volunteers had more staying power. Perhaps the most likable was Neill Macaulay, a twenty-three-year-old history graduate from South Carolina, whose picaresque memoir of his guerrilla adventures, A Rebel in Cuba, is the military equivalent of Kerouac’s footloose epic. In the summer of 1958 Macaulay dropped by the Movement’s Manhattan office, an old brownstone at 305 Amsterdam Avenue on the Upper West Side, which was identified by a black-and-red banner hanging from the second-floor window. Filled with antique portraits of independence heroes and piles of leaflets, the “agreeably chaotic” office was run by a former basketball champion named José Llanusa and staffed with clean-cut young Cubans who had come to study in New York after the island’s universities were all closed. The voluble activists fielded a steady stream of well-meaning gringo volunteers—many of them Columbia students who only wanted to fight during summer break—and politely told most that under US neutrality rules they could only accept financial donations, not recruits.
Unlike Herman Marks, Macaulay had really been in Korea for two years—as an Army postal officer. But he exaggerated his record so convincingly that he was given the contact details for an M-26-7 agent in Havana. After a $10 flight from Key West, upon which he evidently carried his pistols on board, Macaulay lived out the cliché of the self-absorbed American sightseer, getting a “monstrous hangover” from Cuba Libres at the Tropicana, and ending up at a low-budget brothel. Macaulay finally met his underground contact, a “willowy brunette” who had studied at Harvard Business School. A new uprising was starting in Cuba’s fertile agricultural heartland, Pinar del Río, she explained. It was only an hour west of the capital, so Macaulay was taken there by taxi to meet its leader—a twenty-one-year-old former sculpture student known as “Captain Claudio.” Claudio’s mother gave Macaulay a brown paper bag containing a uniform and armband; his pointy shoes from Hong Kong, purchased when he was stationed in Korea, were admired by all. He had become a rebel overnight.
The guerrillas expected Macaulay to fit the stereotype of Americans, he says—that is, “hungry, strong, aggressive, brave, smart, jovial, instructive, and entertaining”—and he did his best to oblige. His rudimentary Spanish kept his compañeros in hysterics, as did his tales of the Lone Ranger (El Llanero Solitario) and Speedy Gonzales (El Rápido). His confusion of the Cuban nickname for hand grenades—piñas, or pineapples—with pinga, penis, was a perennial favorite. There were drunken nights of bonhomie when the guerrillas taught Macaulay to swear in Spanish (“I am going to shit on your mother” was one Cuban classic from Claudio that silenced everyone). His proudest moment may have come when a commander praised him as un americano con cojones, “an American with balls.” But the partisan war also involved brutal, raw encounters. There were bloody skirmishes in the verdant countryside around Viñales, long a popular tourist destination for its ravishing limestone protrusions called mogotes. Macaulay witnessed innumerable executions, usually by hanging to save ammunition—of chivatos (“snitches”), SIM officers, and, most difficult of all, three high school‒age deserters.
FEW AMERICAN REBELS had political notions beyond a vague longing to be a “freedom fighter,” conjuring Fidel’s camp as a Latin revival of Valley Forge. One who did have a broader sense of politics was Don Soldini, a loudmouthed Staten Island kid from a radical family—his grandfather had been a Wobbly, a member of the militant International Workers of the World labor union—who bounced back and forth at a manic pace between the US and Cuba, getting into trouble at every stop. Soldini first won the rebels’ trust by showering pro-Castro pamphlets over Yankee Stadium during a televised World Series game. At age eighteen he traveled to Santiago, where he joined riots after the murder of Frank País; by the spring of 1958 he made his way to the Sierra Cristal, where he fought with Raúl’s column before being wounded in the neck. After that, he took up arms smuggling. He was soon apprehended by SIM in Havana, beaten up, then given a shovel and told to dig his own grave by the light of a squad car. He claims he was spared only by incessantly repeating that his uncle owned an Italian restaurant in New York and was a close personal friend of Batista.
Back in Manhattan again in late 1958, the irrepressible Soldini came up with a new plan when M-26-7 agents showed him the “avalanche” of letters from Americans now begging to join the war effort. He invited some seventy of the most promising candidates to Miami, where he began to organize his own “gringo column” along the lines of the Abraham Lincoln Brigade in the Spanish Civil War. Most of the volunteers were drifters and dreamers. “It was a bunch of assholes, really,” Soldini later told the historian Van Gosse; his only real criterion for membership was that recruits could pay their own expenses. Like Soldini himself, they were drawn to Fidel’s rebellion because its goals seemed so black-and-white: “I loved it. I truly loved it,” he recalled of his time as a guerrilla warrior in Cuba. “With all the privations—hunger, thirst, dysentery . . . I mean, this [was] pure idealism, pure passion. Batista the bad guy, Fidel the good guy—I’m on the side of the good, how great can you go?” The “gringo column,” sadly, never left Miami.
THE SPOTLIGHT OF history has fallen more directly on another yanqui soldier in Fidel’s fold, William Morgan. Thanks to two biographies, a New Yorker article, a PBS television special, and a planned film produced by George Clooney, Morgan has today become almost as celebrated as he was in 1958, when US journalists first began to write him up and newspapers ran dashing portraits of him in rebel uniform. As writer David Grann observes, “with a stark jaw, pugnacious nose, and scruffy blond hair, he had the gallant look of an adventurer in a movie serial, of a throwback to an earlier age.” One reporter at the time, impressed by Morgan’s straight-talking manner, dubbed him “Holden Caulfield with a machine gun.”
A more accurate literary reference may be Jay Gatsby, since Morgan’s story is a parable of American reinvention. Until he shipped off to Cuba, he was a lost soul who failed at everything he did. Raised a Boy Scout in a middle-class home in Toledo, Ohio, Morgan could have grown into a pillar of the Midwestern community; instead, impetuous and restless, he took to stealing cars in his mid-teens, ran away from home, and drifted through a string of odd jobs on the fringes of the law. While serving in Japan as a GI, Morgan was arrested when he went AWOL to visit his local girlfriend, then broke out of military prison. He spent three years doing hard labor and was dishonorably discharged from the army—the very definition of a loser in the patriotic 1950s.
At this point Morgan’s biography becomes hazy and fantastical. Working as a fire-eater in a Florida circus, he married the snake lady and had two children. Then at the age of twenty-nine he decided to shed his former life like an old skin. On the day after Christmas 1957, Morgan ran away again—this time to join the Cuban Rebel Army. His road to a new life was swaddled in lies. Wandering Havana disguised as a rich tourist in a white linen suit and shiny shoes, Morgan made up appealing stories about his military service—at one point saying he had been a World War Two paratrooper—and told underground contacts that he wanted to avenge a friend who had been murdered by Batista’s men. Morgan was chubby, tattooed, and out of shape; he could also barely speak a word of Spanish. Nevertheless, an agent of the Revolutionary Directorate agreed to take him to join their forces in the Sierra Escambray, which could be reached in a day’s drive.
The troop of thirty guerrillas Morgan found there were a scared bunch of near-adolescents with almost no combat experience. Their leader was a waifish, bespectacled ex-student named Eloy Gutiérrez Menoyo whose brother had died leading the attack on the Presidential Palace in March. At first the Cubans regarded the pudgy American with suspicion. They hazed him with brutal all-day hikes, leaving him sunburned, exhausted, and covered with scratches from hostile foliage. (“I am not a mule!” Morgan finally bellowed.) Morgan lost thirty-five pounds but stayed the course: he had been cashiered from one army, he would not drop out of this one. Before long, he was teaching his compañeros marksmanship, judo, knife throwing (a talent he picked up in the circus, not the military), and Boy Scout tricks like using a reed to hide underwater.
Morgan’s rudimentary Spanish nearly got the whole group killed when he started firing prematurely on a passing army patrol. Vowing to improve, Morgan began pointing to every object and asking “¿Como se llama en español?” His next encounter was far more successful. When some two hundred enemy soldiers were spotted moving in single file, Morgan arranged the guerrillas in a U formation to ambush the advance guard. He then rallied the wavering rebels by marching at the enemy alone like John Wayne, his rifle blazing. (“We thought he was insane,” one companion admitted.) The victory bolstered morale and won over local peasants. Morgan now found himself an esteemed member of the DR’s dysfunctional family and began to rise through the ranks.
Rumors about the gringo guerrilla filtered out. Worried that he might be stripped of his US citizenship, Morgan wrote a florid statement entitled “Why I am Here” and sent it—needless to say—to Herbert L. Matthews of the New York Times. “Why did I come here far from my home and family?” he mused. “I am here because the most important thing for free men to do is protect the freedom of others.” Morgan had seen wondrous things in Cuba, he said: “Here, the impossible happens every day. Where a boy of nineteen can march twelve hours with a broken foot over country comparable to the American Rockies without complaint. Where a cigarette is smoked by ten men.” Matthews tidied up the letter and published parts of it in a story. He described Morgan with approval as a “tough, uneducated young American” and included a plucky snapshot of him posing with other rebels. It appeared just before Morgan’s thirtieth birthday. At last he was a somebody, a contender.
In July, Morgan was promoted to comandante, the only foreigner apart from Che himself to reach the position. Not long after, Batista posted a $20,000 bounty on his head.
MORGAN’S RELATIONS WITH Che when he first arrived in the Escambray were frosty, to say the least. Like the other DR guerrillas, he was annoyed that the Argentine assumed he could simply take command. The two foreigners were also polar opposites: Morgan, the barely educated, happy-go-lucky Midwesterner, did not trust the monkish, cerebral Argentine. The “Second Front of the Escambray,” as Morgan’s DR group grandly called itself, was also politically conservative, and its leaders got into heated arguments with the radical Marxist interloper Che over such thorny subjects as land reform. There is one appealing report in the Miami Herald that Che and Morgan faced off in a mountain clearing with troops on either side, challenging one another to “draw,” cowboy-style, but sadly it appears to be fiction. The closest the pair got to blows was when Morgan sent a letter demanding the return of some weapons; Che ignored it. Fidel’s right-hand man regarded the DR with contempt as comevacas, “cow eaters,” who preyed on helpless peasants. Nor did Che take the American’s rank seriously, joking that there were more comandantes in the Second Front than there were foot soldiers.
Perhaps the only thing the two had in common was that they both fell in love with santaclareñas (“girls from Santa Clara”). One day, Morgan arrived in camp—riding a white mare and whistling the theme song from The Bridge on the River Kwai, no less—when he spotted a petite nurse named Olga Rodríguez. A former urban agent, Olga had been forced to flee disguised as a man, cutting her hair short and hiding her face beneath a cap like a Shakespearean heroine. Morgan came up behind her, drawled, “Hey, muchacho,” and pulled the cap down over her eyes. Olga later confessed that she was impressed by the thickset gringo with his carefree swagger, even though his Spanish could still use serious work: for a time he called her Olgo, until she pointed out her name’s feminine ending.
One day, out of the blue, William took her hand. She later recalled stammering: “I don’t know you. I don’t know anything about you.”
He replied: “The past is already past.”
“Now is not the time—or the place. We are in a war.”
Her resistance did not last. He sent her bunches of wildflowers and love letters: “When I found you, I found everything you can wish for in the world,” he wrote. “Only death can separate us.” She slowed down her machine-gun-fast, argot-riddled Spanish and his language skills improved. They spooned during bombing raids and whispered to one another, “Our fates are intertwined.” A single photograph survives of them together in the mountains, both cradling rifles and hugging one another casually with spare hands—Morgan with a dense beard, Olga now letting her hair grow wild. But she had dark intimations: “From the beginning, I had this terrible feeling that things would not end well.” In November, orders arrived for Morgan to lead his guerrilla platoon into the plains. Olga had to stay behind, so they slipped off to a farmhouse to be married. Beforehand, Olga had her first bath in months and borrowed a fresh blouse; Morgan washed his clothes and shaved (something of a shock; she barely recognized him beardless). The farm owners laid out tropical fruit for the wedding feast.
In one of the most touching courtship gestures of the insurgency, Morgan fashioned Olga a wedding ring from a leaf. Before a handful of witnesses, the lovers promised to honor one another, “Hasta que la muerte nos separa,” “Till death do us part.” The marriage was consummated in a starlit field, and Morgan left a few hours later. “We barely had time to kiss,” Rodríguez summed up. As a wedding present, Morgan left behind a parrot that he had trained to screech sweet nothings such as “We-liam” and “I love you!” But to Olga’s distress, one day it flew off. It seemed an ill omen.
THERE WOULD HAVE been many more yanquis in Cuban battle lines had some of the zany pro-Fidel plots succeeded in the US. On March 28, 1958, for example, a Coast Guard gunship rammed a shrimp trawler leaving Brownsville, Texas, and boarded it to find thirty-four militiamen wearing uniforms with M-26-7 arm bands trying to emulate the Granma landing. They were all New Yorkers aged from seventeen to fifty-two, including a medic and a chaplain, under the command of a former construction worker named Arnold Barrow; also on board was a sporting goods store owner who had supplied the $20,000 worth of weapons loaded in the hull. As American citizens, they were all arrested under the Neutrality Act. “I feel our rights are being violated,” Barrow complained. “We are fighting for democracy in Cuba and the United States should help us.” A photo appeared in the New York Times of them sitting on a dock and waving cheerfully. All sat out the revolution in prison.
By late 1958, every major US city had its Movement sympathizers: gangs of bomb makers were busted in Brooklyn and Chicago; a group in Los Angeles was caught with machine guns. The going rate to hire a fishing boat to ship arms from South Carolina, a hub for America’s gun culture, to Cuba, was $2,000. Many decided that a light plane was more efficient: Fidel now had several secret airstrips; Raúl had no less than seven.
The main locus of pro-Castro support now became Miami, which seethed like an Art Deco Casablanca. The tourist mecca was also a “plotters’ playground,” Time reported in September, “a hive of revolutionaries . . . where hardly a day goes by without at least one new plot brewing.” Its 85,000-strong Latino community had its fingers in a smorgasbord of nationalist causes in Central America and the Caribbean, but it was the Cubans who were the busiest and most imaginative. They were drawn from every social class—one cell was said to be led by a restaurant busboy—and they took great risks, since the city was also filled with FBI agents and Batista spies, which led to shoot-outs and long-distance car chases. Cubans caught smuggling arms could have their visas revoked; luckily, Florida judges were sympathetic and resisted deporting activists to their deaths.
Haydée Santamaría was sent to Miami in April to beef up M-26-7 fund-raising efforts, slipping onto an Air Cubana flight from Havana in disguise. She was revulsed by Florida’s “Magic City”: “This is the most unpleasant place on earth,” she wrote to Celia, “so much loneliness . . . at times I feel such a desire to be [home] that I have to control myself not to just run away.” (The young Che had a similarly negative reaction when he was stuck in Miami six years earlier on his shoestring travels. Crashing on a friend’s couch and working as a dishwasher, he bummed beers and french fries from fellow Argentines on the beach. But he left the US appalled at the South’s racial segregation and resentful that Florida police were suspicious of him for his political views.)
Regardless of her objections to Miami, Yeyé proved to be an inspired fund-raiser, hosting Spanish classical guitar concerts and theatrical events with up-and-coming Cuban playwrights. Wealthy exiles opened their checkbooks; the less well-heeled bought portraits of Fidel for $1. By fall of 1958, she was raising between $12,000 and $15,000 per month, much of which was funneled to freelance arms dealers up and down the Florida coast. Miami had many assets for conspirators, she discovered: it offered a coastline porous with swamps and islands, dozens of private airstrips, and policemen keen to improve their meager $300-a-month salaries. For a modest payoff, law enforcement would, Yeyé discovered, “give us the vista gorda,” the blank, unseeing eye. Its shores became as fertile a home for filibusters, or gunrunners, as it had been in the pirate era. Car trunks were filled with smuggled rifles; closets of holiday houses were piled high with grenades; ammunition caches were buried at remote beaches. The Trade Winds apartment complex in South Beach doubled as a dynamite storehouse; a police raid turned up nine hundred sticks. On the tourist ferry from Key West to Havana, ten men were arrested shipping arms in false gas tanks of secondhand Chevrolets. There is no record of how many arms slipped through the Coast Guard net, but Time magazine estimated $200,000 worth in September alone. That same month, a patrol boat chased down the Harpoon from Miami with thirty-two would-be militiamen on board until the captain ran aground in mangroves. The men put up a fight: one tried to fire his machine gun, but it jammed; another pulled the pin of a grenade but it blew up in his hand, taking a finger.
The FBI was less indulgent with the Cuban exiles than Miami police, enforcing US “neutrality” by harassing M-26-7 activists while leaving Batista’s agents untouched. In February, the FBI even arrested the high-profile ex-president Prío for financing military expeditions. The elegantly dressed figure was walked in handcuffs from his penthouse in the Vendôme Hotel in Miami Beach to the police station, where he spent a night in the cells and was eventually fined $9,000. Latin Americans were outraged at Prío’s humiliating treatment, especially since the US had just given asylum to a bloodthirsty dictator who had been forced to flee Venezuela in disgrace. It was yet another example of American double standards, it seemed.