As the U.S. has intensified its pressure on Cuba, since the very first day of President Donald Trump’s second term and continuing thereafter by reinstating Cuba on the "State Sponsors of Terrorism” list, it has triggered a comprehensive series of financial, commercial, humanitarian and military sanctions.

In January 2026, following Venezuelan President Nicolas Maduro’s abduction, Trump declared, "Cuba is ready to fall.” By late January, he had declared a "national emergency” regarding Cuba and threatened oil suppliers with severe sanctions if they delivered fuel to the island.

On May 1, the Trump administration imposed sanctions on all businesses linked to the Cuban economy. This, combined with the existing fuel embargo, plunged the island into an unprecedented economic collapse. Indeed, The Economist magazine reported in May 2026, that the Cuban economy would shrink by 7.2% by year-end, and it is not even clear where the blockade will lead in the coming months.

U.S. Secretary of State Marco Rubio stated that Cuba’s economic system is "irreparable” and that those in power in Cuba cannot resolve this. Defense Secretary Pete Hegseth, in a recent congressional hearing, characterized Cuba as a threat to U.S. national security.

According to Cuba’s electricity authority, the arrival of a single Russian tanker temporarily reduced the proportion of the island affected by power outages from 60% to 30%, but this relief lasted only a few weeks.

In particular, between May 6 and 18, the capital Havana and other areas experienced 24-hour uninterrupted power outages. Refrigerators stopped working, food spoiled, surgeries were canceled, and infant mortality rates doubled.

CIA director visits Cuba

CIA Director John Ratcliffe traveled to Havana on May 14 and met with Raúl Castro’s grandson, Raúl Guillermo Rodríguez Castro, Interior Minister Lázaro Álvarez Casas, and the head of Cuba’s intelligence services.

Before Ratcliffe’s visit, a delegation from the U.S. State Department had traveled to Cuba and conveyed several demands. Among these were demands that Cuban President Diaz step down, that a new president be elected through elections, and that political prisoners be released within "weeks.”

The demands also included resolving claims regarding U.S. property confiscated by the Cuban government and the operation of Starlink satellite systems on the island.

However, in response to the U.S.’s other demands, the Diaz-Canel government announced on March 12 that it would release 51 political prisoners opposed to the Cuban regime. It even stated that dissident Cuban investors living in the U.S. would be able to invest in Cuban private-sector companies, own businesses and property on the island, and even form partnerships with state-owned enterprises.

According to the Miami Herald, the purpose of the trip was to personally convey President Trump’s message that the U.S. is prepared to engage in serious discussions on economic and security matters, but only if Cuba makes fundamental changes.

The CIA’s public announcement of this trip is not merely about creating a news narrative. It is a declaration that Cuba is responsible for everything that happens from now on.

In addition, among the demands was that the Cuban government not host Chinese and Russian military and intelligence bases. The demand that Cuba sever its ties with China and Russia was explicitly stated.

In this context, a $100 million U.S. aid offer, intended not for the Cuban government but for Cuban Catholic charities, was rejected by Cuba. This is because this amount amounts to approximately $10 per Cuban, but Cuba viewed the U.S. proposal, which did not address Cubans’ needs for hospitals, food and fuel, but instead provided funding to civil society organizations, as a propaganda effort by the U.S. government rather than a realistic goal.

Later, Cuban President Diaz-Canel stated in a social media post that he would accept the aid only on the condition that it be delivered in full compliance with universally accepted humanitarian aid practices.

Indeed, details of the meeting between Ratcliffe and Cuban officials emerged just hours after Ratcliffe departed from Cuba, and he revealed to USA Today that the U.S. Department of Justice was preparing an indictment seeking the death penalty against Raúl Castro.

In fact, representatives from both countries met at least three times between February and May 2026. However, tensions in the Caribbean reached a peak due to the sanctions imposed on the Cuban military-owned business conglomerate GAESA and the lawsuit filed against Raúl Castro.

On the Cuban side, the presence of Colonel Raúl Guillermo Rodríguez Castro – Raúl Castro’s grandson, known among the people as "El Cangrejo” (The Crab) – in many of the recent dialogue initiatives between the U.S. and Cuban governments clearly demonstrates the regime’s dynastic tendencies. This situation is causing unease among the so-called "old guard” ideologues, Communist Party members, and intelligence-linked revolutionaries in Cuba. Through GAESA, Rodríguez Castro maintains international business connections. These ties led the U.S. to view him more as a capitalist businessman than a communist, and to regard him as a potential partner.

What to expect?

In this context, Washington will likely continue to increase political and economic pressure on Cuba until the Díaz government steps down. The goal is most likely not direct regime change, but rather to create a controlled political transition process.

Despite U.S. military activity and surveillance flights in the Caribbean, there are no signs indicating that a direct ground operation is imminent. The U.S. does not face an operational theater similar to Iraq or Panama.

Therefore, in the near term, a U.S. military intervention or airstrike against Cuba is not expected. In the medium term, there may be airstrikes targeting strategic and limited objectives, but talking about a ground invasion is not a very realistic prospect.

At this point, there are three scenarios before us:

Scenario one is controlled compromise, in which Havana accepts certain economic reforms proposed by Trump, the U.S. eases some of its sanctions, and Cuba gradually integrates into the global capitalist system.

The second scenario is intra-regime division. According to this, a portion of the military and economic elite surrounding GAESA reaches an agreement with the U.S., while another portion resists. In this case, the system undergoes an internal transformation.

The third scenario is social upheaval. Under this scenario, an energy crisis, food shortages, and migration pressures combine to erode state capacity, triggering an uncontrolled transition process.

As of today, market and intelligence indicators point to a combination of the first and second scenarios. Therefore, interpreting the 2026 Cuban crisis as "the end of the Castro regime” would be an oversimplification.

From the perspectives of Cuba’s other key international partners, China and Russia, Cuba is one of the last strategic observation points in the Western Hemisphere. However, China did not raise the issue of Cuba at all during its summit with Trump in Beijing. Russia, meanwhile, has diverted its oil tankers away from Cuba whenever faced with U.S. pressure, while making largely empty promises regarding aid.

Therefore, Washington’s objective, which is to establish influence through elite transformation and economic integration rather than military intervention, stems from the belief that military intervention is not an option for China and Russia.

Considering that no elements of resistance have emerged that would prompt the U.S. to bring a military option to the table, this situation demonstrates that the U.S. can indeed extract what it wants from Cuba through "intelligence diplomacy.”

Consequently, the U.S. will continue to increase pressure on Cuba. However, at this stage, it is seeking to achieve results through economic pressure, diplomatic maneuvers, and intelligence-based negotiations rather than military intervention.