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  • James Houser

December 28, 1958 - Che Guevara & the Battle of Santa Clara

Updated: Jun 11, 2021

December 28, 1958. A small force of guerrillas descends from the hills around Havana, on their way to confront ten times their number of Cuban Army troops. The leader of this Communist band isn’t even Cuban, though; he’s an international revolutionary whose face will become famous worldwide. At the Battle of Santa Clara, Che Guevara will open the way to Havana and complete the Cuban Revolution. And 60 years later college kids have his face on a T-shirt…for some reason.

Che Guevara is one of those people who seems larger than life. He inspires strong emotions both positive and negative, and the iconic picture on the ubiquitous T-shirt mean that his face is instantly recognizable even to those who have never heard of him. His life seems almost literary, like a Greek tragedy or a postmodern novel – depending, of course, on how sympathetic you are to his point of view.

It helps that Che was a prominent public figure and a prolific writer who was never shy about his ideals or his past. He authored a book on military theory, called “On Guerrilla Warfare,” based on his experiences in the Cuban Revolution. This work is probably one of the more important military texts of the post-WWII period, since it lays out in detail how to overcome a central government from the mountains or the jungles – you know, like almost every war of the 20th and 21st Century. Che also wrote memoirs, pamphlets, and left an extensive diary and voluminous other writings. His memoir “The Motorcycle Diaries” stands as a beacon of iconoclastic counterculture and the rejection of modernist views. Few people have left as much material to interpret, and few have been so striking and strident in both their ideology and their genius.

Of course, the fact that Che was a dedicated Communist revolutionary is divisive. His idealistic belief in the class struggle, his commitment to global revolution, and his martyrdom at the hands of the CIA all help to make him a romantic figure embodying rebellion and international leftist causes. It helps that Che’s writings and persona make him appealing on a personal and empathetic level: in short, a heroic figure of poise and ability. On the OTHER hand, Che is often reviled as an authoritarian perpetrator of vengeful violence, a global bomb-thrower and fifth columnist. And this side, while usually fueled by right-wing sentiment, has a point. Che constantly supported authoritarian communist causes, presided over revolutionary tribunals in the aftermath of the Cuban Revolution, and never shied away from violence to advance his aims. Che Guevara undoubtedly has a lot of innocent blood on his hands – but to be fair to Che, so does almost every major figure of the 20th Century. To treat him as a uniquely wicked figure would indirectly condemn every American president and public official.

So let’s dive into Che Guevara.

Che Guevara was born in Argentina on May 14, 1928, to a mixed-race family of Spanish and Irish roots. Che’s father Ernesto Guevara Lynch always remarked that the blood of Irish rebels flowed in his son’s veins, and while this probably left little cultural impact, Che’s methods and romanticism bore a remarkable resemblance to the Irish revolutionary cause. Che’s relatively leftist family gave him a close “affinity to the poor,” and his literary upbringing exposed him to a wide breadth of authors from a young age. Che was…an intellectual, no other way to describe it, a remarkably well-read young man. He read William Faulkner, Rudyard Kipling, John Keats, Karl Marx, Franz Kafka, Vladimir Lenin, H.G. Wells, Buddha, Aristotle, Bertrand Russell and Friedrich Nietzsche. Far from being a scruffy vagabond, Che was by leaps and bounds more educated than the average kid wearing his face on a shirt.

In 1948, Che entered the University of Buenos Aires to become a doctor. During his vacations, he made long trips across South America on a motorcycle, during which he visited Peru, Brazil, Colombia, and Chile among other countries. These experiences, culminating with a visit to Miami, Florida, permanently altered his worldview and formed the basis of his political beliefs. Che came to see all of Latin America as a connected and oppressed culture living under the specter and iron hand of the United States and its capitalist menace. Struck by the meagre poverty and pitiless working conditions he observed, he was so affected by hunger, disease and maltreatment that he became personally committed to the Communist cause. This sentiment was only reinforced during his visit to Guatemala in 1954, where he personally observed the CIA-assisted Guatemalan coup that replaced a socialist-leaning government with a military dictatorship.

It was these experiences that Che would document in “The Motorcycle Diaries,” and these experiences eventually led him to his life of revolutionary sentiment. While many of his later actions would make it difficult to sympathize with the man Che would later become, it is hard not to understand his sentiments. As a relatively educated, privileged young radical thinker who was able to travel and observe a great deal of suffering, he had the ability to empathize with the downtrodden and sought someone to blame for their plight.

While the United States was certainly not the only force at work in Latin America, and much of the area’s plight was its own doing, American intervention certainly did not make it better. The Guatemalan coup of 1954 is one of the more prominent examples of American interference on behalf of their puppet governments in Latin America, but such actions had been going on for a long time. As Che became convicted – something like a religious conversion – of the perfidy of American imperialism and aggression, his eyes were inevitably drawn to what he saw as the most prominent uprising against this wicked force: the Cuban Revolution.

While working as a doctor in Mexico City in 1954, Che fell in with a set of Cuban exiles from the regime of Fulgencio Batista. Batista had seized power in 1952 through a military coup after cancelling the elections. While Batista’s regime was widely seen as American-backed and a capitalist tool, the United States was none too happy to see this dictator take power. Nevertheless, American interests prevailed; Cuba was a country under widespread American commercial and political influence, and Batista was seen by the Eisenhower Administration as a key ally against the rising tide of leftist insurgency. He might have been a military dictator, sure, but he was OUR military dictator, and the alternative was clear: the Communist revolutionaries that Batista had been fighting would take charge instead.

On July 26, 1953, the revolutionary brothers Fidel and Raul Castro launched an attack on the Moncada Barracks of the Cuban Army in Santiago. This was an attempt to spark a nationwide revolt, but the Castros were decisively defeated by the government forces and forced to retreat. Most of the assailants were captured and executed, and later the Castros were captured as well. In 1955, though, the Batista government freed most of their prisoners. It was their worst mistake, since the Castros fled to exile in Mexico to plan Batista’s overthrow. It was here, in June 1955, that Fidel Castro met Che Guevara and won the young revolutionary over to his cause. The “26th of July Movement”, named after their first attack on the government barracks, had found their revolutionary genius.

Che was not originally a high-ranking leader in the Cuban Revolution; instead, he planned to use his medical training to serve as a doctor for the revolutionary cause. On November 25, 1956, Castro and his small band of 82 men set out for Cuba in a leaky boat. While they landed safely, Batista’s military attacked the Cuban exiles soon after and killed most of them. Only 22, including the Castro brothers and Guevara, survived to link up in the mountains. It was during this battle that Che made a symbolic decision by dropping his medical supplies and picking up a rifle. He had left his medical career behind, and was now a revolutionary leader.

Despite the death of three-quarters of their initial band, Castro’s guerrilla movement began to spread like wildfire throughout the Cuban jungles and mountains. The Sierra Maestra mountains harbored Castro’s band, and they lived in these regions with great hardship and suffering. Che Guevara suffered hunger, disease, and an allergy to mosquito bites, which is never a good thing to have in the Caribbean. But he was also personally affected and inspired by the poverty and misery of the Cuban farmers that he hid and worked with, and this encouraged the renegade doctor to continue on his mission.

As the Cuban Revolution continued, and Castro’s movement grew, Che Guevara became more and more important as a leader and a model revolutionary. He wasn’t just a military man, either; Che pitched himself into the logistics and organization of the movement. He set up schools, bread-baking and grenade-making facilities, health clinics and classes in battle tactics. He even established the Communist newspaper. Very soon, he had risen to basically become Fidel Castro’s second in command of the Cuban revolutionaries, and was even regarded by some as “Fidel’s brain,” the ideological driving force of the Cuban Revolution. Not bad for an Argentine doctor.

But Che had flaws. As passionate, energetic and intelligent as he was, he was firmly in the camp of confrontation over compromise. His zeal could often be disruptive to more rational, measured efforts, and it was this ideological purism and unforgiving determination that often exacerbated difficult situations. In Cuba, Castro was always around to provide the diplomatic and cautionary padding to Che’s blunt and dramatic vigor, but Castro would not be around in the future. Castro also said that Che, while intelligent and a great leader, took too many risks both personal and strategic. Much of Che’s failure in other revolutions would be the result of his dogmatic, uncompromising attitude. It would eventually get him killed.

But for now, Che was demonstrating another great talent: an excellent military and tactical mind. He had begun to take the lead in many of the major battles of the Cuban Revolution. In 1958, after Batista’s continued atrocities against civilians caused the United States to rescind his support, Che Guevara’s column of guerrillas halted a large column of 1500 Cuban Army troops at the Battle of Las Mercedes. This was not quite a victory – it was more of a successful escape – but his tactics in this action were brilliant and would be studied by, among other groups, the United States Marine Corps.

But it was at the Battle of Santa Clara that Che Guevara would win his most prominent tactical victory. With the Batista regime teetering on the brink of collapse, Che led a new column of only 300 fighters west towards Havana on a trying 7-week foot march. Food was scarce, movement was tense and concealed, and the terrain was horrendous, but the guerrillas pushed on. Their goal was the capture of Las Villas province, which sits in the center of Cuba and would divide the island in half. To do this they would not only need to take the province, but also its capital of Santa Clara. As they approached the province, cheering crowds of Cubans greeted the approaching rebels. On December 27, he captured the main port city of Caibarien, and by dusk on December 28, 1958, the rebels were approaching Santa Clara. They would be outnumbered 10 to 1 in the ensuing confrontation.

Che, who led this battle with his arm in a sling, divided his forces into two columns to launch a pincer attack on the city of Santa Clara. During the battle, while his separate forces began to squeeze the city from either side, a panicked Batista sent an armored train to Santa Clara to reinforce its beleaguered defenders. Che dispatched a “suicide squad” of a few brave young men to capture a hill overlooking the railroad. With surprising speed and success, they did so, forcing the armored train to withdraw under fire from bazookas back into the center of Santa Clara.

Che realized that capturing the armored train would turn the tide of the battle. With few options for confronting such a powerful vehicle, his mind fixed on the agricultural university buildings they had captured – and the tractors contained therein. Che ordered his guerrillas to use the tractors to raise the rails leading out of town. When the armored train came out once again to try and fight the guerrillas, it was derailed in the process. His guerrillas forced the enemy out of the train by pitching Molotov cocktails into every nook and cranny they could find. This was an example of Che’s unconventional brilliance, and soon the armored train was in rebel hands along with its huge stores of ammunition and guns.

The capture of the armored train ended up being the turning point of the Battle of Santa Clara. Che’s forces had soon overrun the city, and despite Batista’s radio proclamations that government forces had won and had killed Che himself, Che’s counterpoints on the radio soon gave the lie to Batista’s pronouncements. Che announced that Cuban rebels were converging on Havana as he spoke. Santa Clara, after all, was not far from the capital. The demoralization of the Cuban Army as a result of their defeat at Santa Clara spelled the end for Batista. On January 1, 1959, he packed a bag and fled for the Dominican Republic. The next day – January 2 – Che Guevara and his column arrived to take control of Havana. Though Castro would only arrive six days later, it had been Che and his victory that had won the Cuban Revolution for good.

After Castro’s victory was complete, Che ended up playing a major part in the new Communist government of Cuba. Always more of a Marxist ideologue than his nationalist brethren (largely because he wasn’t, well, Cuban) Che held enormous sway over Cuban government policy from 1959 to 1965, perhaps second only to Castro himself. It was under Che’s auspices that much of the land, education, and health reform was carried out that would make Cuba among the most successful 20th-Century communist states. Many of his reforms, especially industrial progress and monetary policy, failed utterly in the face of all economic sense. Nationalization proved equally embarrassing. Che was a Marxist, with all the social progress and economic inefficiency that always implies. His economic programs were ultimately unsuccessful and marked by a massive drop in productivity. It was during this period that Che attended a memorial service, during which the famous photograph was taken that adorns T-shirts to this day.

It was also under his supervision that the execution of many political prisoners and “war criminals” took place. These executions are highly controversial and disputed to this day; some of his admirers and even some relatively objective biographers claim that Che’s executions were almost all deserved, while others see them as a Marxist witch hunt that caught many innocents in the process. Some accounts portray Che as bloodthirsty, while others portray him as sympathetic – but none depict him as opposed to the death penalty. Che was a radical, and radicals undertake radical actions. There is little doubt that he saw these executions as righteous and necessary, perhaps even a good thing. Several hundred Cubans were executed nationwide during the reprisals, with Che’s personally supervised death toll at somewhere around 100. Bloody, sure, but by 20th Century standards pretty small potatoes.

Che also ended up being the public face of the Cuban Revolution. He was sent on two world tours in 1959 and 1964, where he spoke at the United Nations and visited leaders across the world, including in Egypt, the Soviet Union, Indonesia, Japan and India. Everywhere Che made an impression and close personal connections with fellow Soviet-aligned leaders, but in particular he began to gain an antipathy for the Soviet Union.

Especially after the Soviets backed down during the Cuban Missile Crisis, Che began to appreciate the fact that the Cubans were only a tool in the hands of the Soviet Union. Always a hard-liner, Che had pushed for nuclear missiles in Cuba and confrontation with the great enemy of the United States. As he began to grow bitter towards Moscow, Che started to align more and more with the Maoist Communist bloc led by China. The Soviets and the Chinese, far from being closely linked by their mutual Communism, were split on both international and ideological lines, and Che began to speak openly about aligning with China rather than Russia.

It may have been for this reason, or the failure of his industrial policies, or even his own restless spirit, that Che ultimately left Cuba. Castro’s power was growing, and his old comrade was simply in the way – and causing trouble to boot by thumbing his nose at Castro’s close allies in the Soviet Union. Once again, Che had worn his heart too openly on his sleeve, and Castro was beginning to see the downsides of Che’s mercurial genius. In 1965, Che Guevara abruptly vanished from Cuba with no explanation. Since he had had such a prominent part in Cuban government up until then, the people were confused, until later in the year Castro “produced” a letter from Che proclaiming his commitment to global revolution. Che Guevara had gone underground, off to find another revolution to win.

For the rest of his life, Che Guevara would be a rebel in search of a cause. He would go around the Third World, lending his military and political expertise to whatever movement would take him. He seemed to have accepted that he had done as much as he could do in Cuba – it was Castro’s country, not his – and decided to seek his fortune elsewhere. His first destination in 1965 was the Congo, where he hoped to inspire an Africa-wide Communist uprising against Western capitalism. Che led a set of Cuban revolutionaries to help the Congolese guerrillas against white and Belgian-backed militias.

While he was never racist or disparaging to his fellow revolutionaries, Che was nonetheless a fish out of water in Africa. He spoke none of the native languages, did not understand the local or tribal politics, and demanded commitment to an ideological creed that most Africans did not know or understand. He was hunted, too; the United States government was tracking his movements from a Navy frigate that intercepted his radio signals. Che had no success in the Congo, thwarted by lack of interest in Marxism and infighting between rebel groups. By the end of 1965, a disillusioned Che Guevara withdrew from the Congo with his Cuban survivors. Throughout the remainder of 1965 and into 1966, he would seek refuge in Cuban safehouses in Tanzania and Czechoslovakia, trying to plan his next move.

Che finally decided that, Africa having rejected him, he would dedicate himself to the liberation of all Latin America. He had had pan-Latin American visions of widespread revolution and union since his Motorcycle Diaries days, and believed that a big enough spark could light a flame that would engulf the whole continent. He chose Bolivia as his first target, and after visiting his family in secret one last time in Cuba, arrived in Bolivia on November 3, 1966. Within days, he was heading into the mountains to form a new guerrilla army. The great revolutionary was setting out on his third revolution in a foreign land.

But this would be his last. The Bolivian movement proved no more successful than the one in the Congo. While Che won several battles against the Bolivian Army, he failed to win the support of the other scattered resistance groups, many of whom looked towards the Soviet Union for support – which Che could not abide. His subordinates also failed to keep in touch with Cuba or China, his main sources of support. His tendency towards confrontation and his dogmatic zeal alienated potential allies in Bolivian villages, even as they had impressed world leaders and Marxist ideologues the world over. In short, Che rubbed all his potential friends and many future allies the wrong way. He was too extreme, too radical, too dogmatic. He was just hard to work with, whatever his talents and however great his brilliance.

Che’s enemies finally came to collect. The United States had been after his hide for a long time, and had sent CIA commandos and Army Rangers to support Bolivian efforts against their guerrilla group. They knew Che was in the area, and were looking for an opportunity to nab him. When an informant revealed the location of his camp, on October 8, 1967, the Bolivians surrounded his camp and captured the famous radical. He was brought to a local village, where he was interrogated by the Bolivians. While many villagers expressed sympathy for him and regarded him as charismatic, handsome, and tranquil, the Bolivian President decided this dangerous man had to die – despite American wishes that he be brought to Panama for further interrogation. Che knew his number was up, and seemed to accept his fate. In his last minutes, one of his guards asked if he was thinking about his mortality. "No," he replied, "I'm thinking about the immortality of the revolution."

On October 9, 1967, Che Guevara was blasted apart by a Bolivian soldier who had lost friends to his band of guerrillas. His body was strapped to a helicopter and flown to a nearby town, where he was displayed on a concrete block as a trophy by the Bolivian government. Oddly enough, his long hair and serene face drew many comparisons to Christ, and his supine pose reminded many of Renaissance paintings of the murdered Son of God. Many villagers took locks of his hair, and later leftist governments would raise a massive statue of Che on the spot of his death. He was almost as powerful and forceful in the grave as he was in life.

Che Guevara’s life and death are rightly legendary. A charismatic leader, deep thinker and brilliant military commander, he was undone by his own passions and commitments to a certain idealistic vision of Marxist revolution. Without the restraining, moderating hand of a Castro, he was ultimately doomed to let his fervor and romanticism run away with itself. He tried to be, but could not be, the world revolutionary that he thought the world needed. His quixotic crusades for the cause of global revolution eventually led to his destruction.

As romantic as he was, maybe stop wearing the T-shirts, guys? Does NOT speak well for the success of whatever revolution you envision.

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