What you need to know about how we got here.

The story of Cuba is a bizarre one. It has a destiny based on its geographic position as the gateway to the Caribbean.  It has long been sought after by world powers and somehow remains somewhat of an enigma. The large island is full of friendly people with a very checkered past. For the past 60 years, Cubans have been living under one of the most polarizing and misunderstood leaders of the modern era. They are proud of their country’s past and love to share their history with anyone who will listen. I have collected what I think are the pertinent facts in understanding the last 60 years and why US and Cuban relations have been at a near standstill during my lifetime.

In the early part of the 20thcentury, Cuba was a playground for the mob and American businessmen. The close island neighbor was a popular getaway with spectacular casinos and hotels along with an abundance of rum from the sugar plantations. Cuba provided the perfect backdrop for Americans to get their fix of fun, particularly during prohibition. Fugencio Batista had taken control of Cuba in a military coup and essentially buddied up to the U.S., which overlooked his often-barbaric military rule and turned a blind eye to the human rights violations that plagued his administration. The mobsters and wealthy businessmen in exchange for free reign in Havana generously lined his pockets and supported the military dictator.

Fidel Castro came to power in 1959 after successfully leading a group of guerrilla rebels to victory in the most famous of the Cuban Revolutions. The U.S. supported regime of then President Batista toppled and Batista himself fled Havana on January 1, 1959.  He initially fled to the Dominican Republic but eventually received asylum in Portugal. Castro’s revolution was carried out over nearly three years. The ideals behind the Revolution were complicated and not always shared among the rebels but they generally embodied the ideas of socialism and equality for all Cubans, desiring to free them of the military dictatorship that allegedly exploited the poor in Cuba. The other main driver in the revolution was freeing Cuba from its overshadowing imperialist neighbors to the north, the United States. The overarching goal of this revolution included a unified Latin America but that is a topic all by itself.

Casualties in the revolution occurred on both sides but the guerilla fighters were almost always outnumbered. Much of the success of Fidel and his rebel band was his savvy use of the media.  According to Ernesto “Che” Guevara’s diary of the revolution, the rebels had several lucky breaks as they hid out in the mountains of the Sierra Maestra in Eastern Cuba. They won several skirmishes that allowed them to make small advances but it was the collection of these small victories and the use of reporters and their own “rebel radio” that caused a sense of nationalism to spread over the country. After months of this guerilla style warfare and a series of bad political moves from Batista, Cubans started converting to the Revolutionary movement, called the 26thof July Movement, and Batista’s army started voluntarily surrendering. When Batista realized he had lost control of his own army, he decided that the end was near. He fled Cuba taking nearly $300 million with him. Once news reached the rebels that Batista had fled, Castro’s army marched to Havana victoriously. Castro took the flight of Batista as a mandate from the people and immediately began to prescribe the law without any legitimate legislative body, or direction of authority. He eventually declared himself the new Prime Minister of the island state at the age of 33. It was manifest destiny.

Shortly after taking power, he made a trip to the United States to meet with President Dwight Eisenhower. Perhaps one of the biggest mistakes made by the US was the refusal of the President to meet and cooperate with the young Cuban leader.  Eisenhower instead sent Vice-President Richard Nixon. (Nixon was running for President at the time but lost his bid to John F. Kennedy later that year.)This, in my opinion, was the catalyst for a lifelong standoff with the American government. 

Like any other island nation, natural resources are limited and Cuba needed assistance to jumpstart it’s economy and implement the changes promised by the revolutionary movement. The proud, hotheaded Castro began to seek out allies that could help Cuba financially and ultimately could provide assistance militarily.  When the United States failed to recognize Castro as a leading political figure, which bruised his ego, he began seeking help elsewhere. Enter the Soviet Union.  

Incidentally, Castro was not a Communist initially by most accounts. The Cuban Revolution of 1959 was a Nationalist movement more than anything else. Castro admired Cuban hero Jose Marti and US President Abraham Lincoln. His brother Raul Castro and commandant Ernesto “Che” Guevara were the hardline communists among the rebel group. Make no mistake, however, Fidel called the shots both during and after the Revolution. After all, the Revolution was his brainchild from the very beginning and it wasn’t his first attempt at overthrowing Batista. U.S. companies dominating the Cuban economy, trusted communist advisors, and a desire to finance changes that would solidify his promises to the poor combined to create the perfect storm for the Soviets to swoop in and save the day for the new Cuban government. Diplomatic ties were immediately forged and an initial loan of $100 million dollars created a strong bond between the two states.

US-Cuba relations did an almost immediate nosedive. The new regime began seizing property and companies, largely controlled by American investors. The new “Idealists” including the immortal Ernesto “Che” Guevara, Fidel Castro, Raul Castro, and the Cuban War Hero, Camilo Cienfuegos immediately began making headlines. Shortly after the newfound friendship with the Soviet Union, Castro knew that he needed help to safeguard his power against imperial forces. The Soviet Union responded with thousands of troops to remain stationed on the island and by secretly shipping their nuclear arsenal to Cuba in response to the US nuclear apparatus in Turkey (striking range to the USSR). The Soviet ships came cloaked as an automobile-manufacturing move and not as a military operation. Soon after setup began, however, US spy planes discovered the missiles on the island, which leading to a bitter 13-day standoff dubbed the Cuban Missile Crisis.

Following the nuclear standoff with Cuba and the USSR, President Kennedy imposed an embargo, or blockade as it is referred to in Cuba, on all trade with the island.  At this juncture, Cuba was the sworn enemy of the United States and vice versa. Fast-forward almost 60 years and that trade embargo still exists.  Legal travel to Cuba has been difficult to impossible for Americans without passage through another country acting as a third party. Tensions were lifted somewhat during the Obama administration but then tightened back more recently by President Trump. 

Beginning around 1980, Cuba has struggled economically, in part because of troubled allies, the collapse of the Soviet Union, political complications in Venezuela, and the fall of the communist bloc in Europe. Somehow, Castro managed to alter the strategies of the revolution just enough to maintain tight control of the communist state.  Ultimately, the ideals of the revolution were achieved. Castro put Cubans to work, initiated a major literacy campaign across the island, instituted free healthcare, and made major education reforms. The problem, in my opinion is that Fidel held on to the glory days of the revolution, his ultimate claim to fame, too long instead of evolving and adapting over time. He believed in ideas as prevailing and absolute, but the world around him continued to change.

Fidel Castro died in 2016. I visited Cuba for the first time later that year and thus began my fascination with the Cuban leader as a master of the media, revolutionary triumphant, and political icon. At the time of his death, he and Raul were all that was left (in power) of the revolutionaries of 1959. He was preceded in death by the other iconic figures, Che Guevara and Camilo Cienfuegos. Che, worked in several capacities for the new Cuban Government and then went on to fight in the Congo and Bolivia, where he was captured and executed by the CIA in 1967. Camilo, perhaps the most beloved hero of the revolution, was made commander of the Cuban armed forces following the revolution but did not align politically with the socialist ideas of Fidel. In 1959, less than one year after the revolutionary victory, he and his plane mysteriously vanished on a short flight in the Florida straits and were never recovered. Those deaths left Fidel and Raul Castro at the healm of the Cuban government for the past 50 years or so. At the time of Fidel’s death in 2016, Raul had already been serving as President of Cuba. He resigned in 2018 and Miguel Diaz-Canel took over in April of 2018. 

The world now waits and watches as the life of the last remaining Castro, aged 88 years, and last remnant of a 60-year-old revolution nears the end of his life. Will the Revolution be able to continue despite the huge pressures of globalization? Will there be a political movement of the intellectual community or an armed revolt or will the government start moving in a more capitalistic direction and start abandoning the guiding principles of the last half decade.  Cuba’s history may once again have a chance to re-write itself as it embarks on its fragile and impending future. Will the future cause a rise in nationalism again or a willingness to accept overarching support from larger more powerful neighbors? Cuba libre…


Cuba Confidential by Ann Louise Bardach

Diary of a Combatant by Enesto “Che” Guevara

Cuba Libre (Netflix)

History of the Cuban Revolution Podcast

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