(Photo by White House Photographer Shealah Craighead via Wikimedia Commons/Public Domain)
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Note: This article is the first part of a two-part article series discussing the history and context of Donald Trump’s recent threats against Cuba.
In a White House press conference on March 16th, 2026, United States (U.S.) President Donald Trump stated, “[he] would have the honor of taking Cuba.” Just under two weeks later, on March 27th, in a speech touting his administration’s illegal wars in Venezuela and Iran, he declared, “Cuba is next.”
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Join the Sphere →Shortly after, on May 20th, the U.S. Department of Justice indicted former Cuban President Raúl Castro over the 1996 shootdown of Cuban exile planes. He was the Minister of Defense at the time.
The U.S. has only sought to arrest three foreign leaders in its history: Manuel Noriega of Panama, Saddam Hussein of Iraq, and Nicholas Maduro of Venezuela. All of which were successful. These actions imply that Trump is truly intent on invading Cuba. The U.S. has had a hostile posture towards Cuba since Fidel Castro led his popular revolution against the American-backed dictator Fulgencio Batista in 1959.
The Revolution
After decades of Batista’s military dictatorship, Fidel and Raúl Castro landed in southeastern Cuba on December 2nd, 1956, alongside their newfound comrade Che Guevara. With Batista’s army outnumbering them, the revolutionaries suffered immense losses in the beginning.
Despite these obstacles, the revolutionaries adapted, and Che outlined a highly effective guerrilla warfare strategy that fractured and demoralized Batista’s army. As Castro and his comrades accumulated victories, Cubans joined the revolution in droves.
After a little over 2 years of warfare, Castro and his fellow revolutionaries triumphantly entered Havana on January 8th, 1959. Castro and his popular forces overthrew Batista, forcing him to flee to the Dominican Republic.
The U.S. initially supplied Batista’s regime with equipment and weaponry. However, as his brutality increased and it became evident the rebels were going to win, the U.S. imposed an arms embargo.
The U.S. had quietly supported Castro, sending Central Intelligence Agency (CIA) operative Frank Sturgis to train and equip the rebels. Sturgis was later part of the Watergate break-in.
The U.S. Welcomes Castro
The U.S. was one of the first countries to recognize the revolutionary government’s legitimacy. Castro even embarked on a tour of the U.S., where he met with Vice President Richard Nixon and Secretary of State Christian Herter. Many within the U.S. greeted him as a celebrity. During this trip, Castro stated that Cuba would be neutral in the Cold War between the U.S. and the Soviet Union. Ultimately, the outing was unsuccessful, as Castro was seeking foreign aid and returned without American support.
(Photo via Wikimedia Commons/Public Domain)
The lack of American aid put Castro in a bind; Cuba was desperately poor. To raise revenue for his government’s basic functions and ambitious programs, he implemented several bold policies. He increased taxes, restricted foreign currency exchanges, and passed his first agrarian reform.
This reform, passed on June 4th, 1959, consisted of nationalising all farms over 1,000 hectares (4 square KM), regardless of the owner’s nationality. Castro sought to make the farming sector – which Cuba depended on heavily – more equal. Before the revolution, 9.4% of landowners possessed 73.3% of available farmland.
Foreign and Domestic Enemies
However, as the reform passed, foreign and domestic forces denounced Castro. On June 11th, the U.S. filed a formal protest, and 5 cabinet members resigned the next day. The U.S. and the cabinet members were bothered by the enforcement of sovereignty and the seemingly communist approach.
Castro never declared himself a communist prior to or during the revolution, but there were some communists within the revolution. They started to gain power and influence as the U.S. and Castro’s former revolutionary allies opposed him.
This Cuban power struggle increased to the point that Castro resigned as Prime Minister on July 17th, 1959. He found it increasingly difficult to work with anti-communist President Manuel Urrutia Lleó. Although Castro remained a public figure, popular demonstrations demanded he take charge once again. On July 23rd, Castro returned to his Premiership and replaced Urrutia with loyalist Osvaldo Dorticós Torrado.
Despite his triumphant return, Castro was not out of the woods. Cuba remained poor, unemployment remained high, investment was falling, and the Peso lost 72% of its value.
The Embargo Takes Shape
U.S. President Eisenhower also barred Cuban sugar imports, eliminating Cuba’s largest market. Castro grew increasingly desperate and turned to the superpower that hadn’t given him the cold shoulder.
In February 1960, Cuba signed a trade pact with the Union of Soviet Socialist Republics (USSR), attempting to ease the economic strain, but it could only do so much. Cuba’s problems persisted, and Castro’s plans to solve them became increasingly desperate. One October night, he nationalized 382 businesses and all but two banks. He also nationalized all American firms operating in Cuba without compensation, which America did not take well.
Eisenhower implemented the first Cuba embargo in October of 1960, banning all trade with the island, except for nonsubsidized food and medicine. At the time, Cuba bought 70% of its foreign goods from the U.S. America wanted to suffocate Cuba. However, U.S. allies did not go along with the embargo. Britain and Canada sought to fill the American void. Canada’s Prime Minister, John Diefenbaker, a Tory, stated, “In Canada there does not prevail the aggressive hysteria which blinds the United States”. On January 3rd, 1961, the aggressive hysteria led to Eisenhower severing all ties with Cuba as one of his final presidential acts.
The CIA and The Bay of Pigs
In his presidency’s final year, Eisenhower authorized the CIA to plan an operation to overthrow Castro. The scheme called for bombing Cuban airfields, an invasion force of 1,400 exiled Cubans, and a provisional government in waiting. The operation was meant to be secret; however, news spread quickly across the Cuban diaspora, and Castro caught wind of the plan.
The operation moved forward on April 15th, 1961, with the repainted planes’ bombing run. It failed and alerted Cuba that the U.S. was attacking. Two days later, the exiles (Brigade 2506) landed at the Bay of Pigs. Cuban forces easily spotted them and descended on them 20,000 strong.
(Photo by Miguel Vinas via Wikimedia Commons/Public Domain)
Brigade 2506 fought for two days until they ran out of supplies, surrendering to the government they intended to oust.
The Crisis of Your Own Making
With the quick victory, Castro’s presence and popularity grew, as did his fear. He reached out to the USSR for security. Castro’s fear was well-founded; the U.S. did not take its failure well. It devised increasingly bold schemes to depose him.
Kennedy upped the embargo against Cuba, now banning all trade and financial transactions between the countries. He authorized Operation Mongoose, which called for Castro’s assassination and the sabotage of Cuba’s vital infrastructure and industry, eventually leading to an October 1962 invasion. Operation Mongoose validated Castro’s closeness to the USSR.
Khrushchev, the Soviet Premier, responded to his call and started constructing nuclear missile launchers on the island. The construction went undetected for months, until October 14th, 1962, when a U.S. spy plane photographed the sites. Eight days later, Kennedy announced a naval “quarantine”. The quarantine label allowed JFK to impose a de facto blockade without the consequences of one, mainly war. What followed was thirteen days of posturing, threats, negotiations, and the threat of nuclear annihilation. Eventually, the U.S. and the USSR resolved the standoff diplomatically.
The Soviets agreed to remove the missiles in exchange for an American pledge to never invade Cuba. America also agreed to a second hidden promise to remove its nuclear arsenal in Turkey, pointed squarely at the USSR.
Never Give Up
Despite the world being seconds away from nuclear annihilation, in part due to its Cuba policy, the U.S. continued its attempts against Castro. The CIA allegedly made over 600 attempts on his life.
The military and CIA devised a diabolical program dubbed Operation Northwoods. It called for orchestrating a series of coordinated attacks across Cuba and the U.S. to justify an American invasion. Additionally, they had considered killing Cuban exiles and executing terrorist acts in U.S. cities. In the end, JFK rejected Operation Northwoods.
Although JFK declined the program, Operation Northwoods highlighted the lengths some U.S. officials were prepared to go to destabilize Cuba. Policymakers knew undisguised war was unjustified after the agreement to end the missile crisis, so they turned to covert action and economic warfare.
The U.S. maintained the suffocating embargo against Cuba, leading to shortages of food, water, electricity, life-saving aid and equipment, as well as skilled workers emigrating. The U.S. further complicated the situation in 1982 when President Reagan placed Cuba on the list of state sponsors of terror (SSOT).
The SSOT is a list the State Department publishes yearly, containing countries the U.S. considers to have provided support for acts of international terrorism. Being on that list subjects a country to punitive sanctions.
El Periodo Especial
Placing Cuba on that list further impoverished the population. Nine years later, its Patron, the USSR, collapsed. Cuba lost 21.2% of its GDP, 4.3 billion USD, overnight.
To make matters worse, the U.S. expanded the embargo with the Torricelli and Helms-Burton Acts, banning foreign companies and foreign subsidiaries of U.S. companies from trading with Cuba. America thought it could finally choke out Cuba. The Island survived, but it suffered.
Cubans faced vast shortages and forced rationing, blackouts lasted 20 hours daily, and Cubans lost twelve pounds on average. Millions of Cubans went without necessary medication, and thousands emigrated, choosing to face the ocean’s wrath rather than the domestic suffering.
The Cuban government adapted by relaxing foreign currency controls, allowing for limited private enterprise, and opening itself to foreign investment. It also developed its tourism industry, bringing in important revenues. Cuba had survived another brutal period in its history.
U.S. officials thought the Torricelli and Helms-Burton Acts would “lead to Castro’s ouster within weeks”. He handed power to his brother Raúl in 2008, 16 years after the Torricelli Act passed. Despite failing to oust Castro and bring down Cuba, the U.S. refused to change its approach and normalize relations.
A New “Special Period”
Trump has accelerated the aggressive U.S. policy towards Cuba. He sanctioned and indicted their leaders, choked the Island off from oil and other essentials, plunging the island into a darkness many consider worse than the Periodo Especial. Cubans have even said they feel “the island is slowly dying”.
The lack of oil makes it difficult to farm the land and impossible to transport the little that is produced to the cities. This problem is leading to hunger and malnutrition. Trump has also threatened tariffs on any country seeking to aid Cuba, which makes Cuba even less likely to receive help.
The last time the U.S. openly threatened Cuba this way, they had a powerful ally to back them up, but this time, Cuba does not have Khrushchev to come assist. This is not just Trump’s doing. This is the culmination of six decades of U.S. policy. Since Castro implemented the Cuban revolution’s ideals, America has always been intent on destroying it. Yet, Cuba survived.
Edited by Alexas Vieira
