According to Havana officials, a boat with 10 heavily-armed men in it entered Cuban waters on February 25, 2026. They were intent on infiltrating Cuba and destabilizing the communist regime through acts of terror and terrorism. The Cuban border guards opened fire when the 10 men fired on the approaching patrol boat. They killed four of the attackers and wounded the remaining six. A second Cuban American, who had flown from the United States into Cuba to meet with the infiltration team at the beach, was arrested later.
Details about the shooting are still being revealed, but the event comes amid heightened tensions in Cuba-US relations, as the US has for several weeks been trying to impose a total de facto oil embargo on the island. This latest incident is also reminiscent to the 1960s when Cubans exiles were armed and trained by the CIA to try to enter Cuba and commit acts of sabotage or assassinate leaders of Cuban Revolution.
In my capacity as a specialist in U.S. policy towards Latin America, and a co-author on a history of bilateral diplomatic relations between Cuba and the United States, I am well aware that Cuban exiles have long had paramilitary components.
These elements are encouraged by Washington’s increased sanctions, heated rhetoric and the weakened Havana government.
Cuban paramilitaries exiled
After the Cuban Revolution triumphed and Fidel came to power, the U.S. government’s policy towards the new regime was hostile almost immediately.
The Bay of Pigs invasion was organized by the CIA in 1961 under the leadership of President John F. Kennedy. It involved exiled Cubans who were attempting to overthrow the Castro government.
After thwarting ill-fated Bay of Pigs invasion, pro-Castro troops pose on Playa de Giron in Cuba. Graf/Getty Images
The attempt at invasion, according to Theodore Draper’s book, was “a perfect failure.” After that the agency hired a few of those invaders in order to continue the irregular war on Cuba. Operation Mongoose was a multifaceted Kennedy-era program that included diplomatic, economic and political pressures, as well paramilitary forces, aimed at toppling the Cuban regime.
Financial support from the CIA for paramilitary exile groups continued until late 1960s.
It was then phased out due to their lack of effectiveness. The paramilitary groups in exile did not give up their efforts to overthrow Castro with force.
Alpha 66, Omega 7 and other groups fought against Cuban authorities for many years under tacit U.S. backing. Richard Nixon responded to Coast Guard attempts to arrest Alpha 66 members in 1971 by writing, “We shouldn’t inhibit Cuban exile activities against their homeland.” Five years after that, Orlando Bosch, Luis Posada Carriles and other paramilitary leaders orchestrated the attack on Cubana Flight 455 which killed all 73 passengers.
A change in attitudes
The paramilitary organizations became frustrated by their failure to overthrow the Cuban regime. They turned inward.
These groups began a series of assassinations and terrorist attacks in the 1970s. They targeted Cuban Americans, who spoke out for rapprochement between their homeland and Cuba. Omega 7 assassinated two Cuban Americans, members of the Committee of 75 who had traveled to Cuba in 1979 to negotiate the release of political prisoner with Castro.
Ronald Reagan, while not a friend to Castro, launched an aggressive crackdown against the paramilitary organizations based in the United States, and convicted a few of its members.
The terror attacks have subsided but some Cuban-American extremists still retain a martial spirit. In Florida’s Everglades, where the largest Cuban Diaspora in the world lives, small groups continue to conduct weekend training. Over the years some weekend warriors tried to enter Cuba. They are almost always quickly arrested by Cuban law enforcement. This latest firefight, though violent and unusual, seems to be one of the most recent.
Increased US hostility towards Cuba
These incursions have increased over the past few years, as have attempts to solicit acts of social media sabotage by Cuban Americans. Relations between Cuba and America are now at their worst point in many decades.
Cuban-U.S.
Relations are at an all time low. Yamil Lage/AFP via Getty Images
Donald Trump, in his first term as president, reversed the thaw of President Barack Obama on Cuban relations that began in 2014. He imposed the most severe economic sanctions against Cuba since the 1960s. Joe Biden kept most of these sanctions, even though the Cuban economy was suffering during the COVID-19 epidemic.
In his second term as president, Trump is tightening the screws by cutting Cuba’s supply of oil from Venezuela.
He also threatens other countries with sanctions if they ship oil to Cuba. This has led to a dramatic, unprecedented decline in the economy of Cuba that could lead to a humanitarian crisis.
Trump, as well as Secretary of State Marco Rubio who made his career in politics by being one of the loudest anti-Cuban members of Congress, both declare Cuba to be a failed country and forecast its impending collapse.
The White House’s predictions, coupled with an unsustainable economic situation on the island have led to the expectation that Cuban government will not survive. Cuban American activists may conclude in this climate that their long-awaited moment is here. They might even decide to head down to the south and take up arms to see, or participate in, the fall of the Cuban government.
Cuba, despite the claims of the White House, is not a failing state.
Cuban authorities are still capable of maintaining order on the island and protecting its coast, as was proven by the ten people who allegedly attempted to enter the country.
Trump, his advisers who are hawkish, such as Rubio, seem to be trying to subdue Cuba, just like they did in Venezuela.
There are no signs that the Cuban regime is crumbling and there’s no organized opposition.
Cubans are fiercely patriotic and will not accept a deal which requires them to give up their sovereignty to the United States by changing their economic or political system.
The Cuban economy is going to continue to decline if Washington and Havana do not reach a diplomatic agreement. This will be due in part because of the U.S.
embargo and the oil blockade. The Cuban people will suffer more and other exiles may launch paramilitary missions to exploit Havana’s weaknesses.
