Why Trump Will Not Destroy Cuba

Tim Anderson

Source: Al Mayadeen English

22 Jun 2026 10:55

Despite intensifying US pressure and blockade measures, Cuba’s tradition of resistance, strong social organization, and decades of preparation against foreign intervention make regime change or military conquest unlikely.

Donald Trump has tightened the six-decade-long US blockade of Cuba (it has never been simply an “embargo”) and is threatening to take over the little island nation, but, as this article explains, he will fail.

Trump may be looking for a new conquest after his apparent success in Venezuela followed by a resounding defeat in Iran. The Venezuelan method seems his best bet but, as I will explain, conditions are not favourable for Trump using that “option” in Cuba. This is despite the conditions of the Gaza-like siege.

Conditions in Cuba are severe; I was there in May 2026 and saw the depth of the hardship. When fuel ran out from the Russian ship Anatoly Kolodkin, which arrived in Cuba in March, there was very little ordinary transport even in the capital Havana. There are some offsetting factors which I will outline below, but most bus and truck transport has stopped. Lack of fuel means great difficulty in transporting food, regular blackouts in some areas and failure of water pumps. There are shortage of most basic goods, growing malnutrition and fatal events (during blackouts) for those on hospital life support systems.

Shipments of food and medicine aid from China, Russia, Mexico and some other Latin American countries are very welcome, but the fuel blockade is the most crippling factor. Cubans have suffered various degrees of siege for decades. Current shortages are as bad as those of the 1990s, which caused several years of economic contraction and depression, after the collapse of trade with the former Soviet Union. Many predicted that Cuba would collapse back then; but the system held firm and introduced reforms such as opening to tourism, licensing various small businesses and allowing joint venture foreign investment. Today, the few tourists in Cuba are mostly Cuban-Americans visiting their families. With no refueling of long-haul jets, inward flights have been few and far between.

Nevertheless, a group of 15 US intelligence veterans have warned the Trump regime that “the same people who keep 57 Chevrolets on the road with a coat hanger will wreak havoc against a foreign imposed regime”. Like Iran, albeit in different ways, Cuba has spent decades preparing for another invasion attempt, after defeating JFK’s invasion attempt at the Bay of Pigs in April 1961.

Russian military analyst Dmitry Kornev points out that Trump has three possible military paths of attack: (1) a “limited surgical operation” along the lines of the January 2026 coup in Venezuela, (2) a “full scale air campaign” and (3) a “naval blockade and economic strangulation”. The third is already in place, the second is “unattractive” due to a likely “global backlash” and the fact that aerial bombing alone has never led to foreign controlled regime change.

Further, the Cuban people’s history of resistance will be a serious obstacle, as sociologist Anibal Garzon points out: “If there is a US invasion of Cuba, the island may not have the best army, the best technology, or the best weaponry, but it does have a people with great courage to resist the empire that has been besieging and blockading it for decades”.

From observations over recent years, Trump’s intervention “options” seem driven and constrained by four factors: first, he wants to present the image of a leader who can impose his will by threats, bluster and the idea of himself as a skillful “deal” maker; second, at the same time he is loss averse, wanting to impose his will without great risk of defeat or of losing many US lives (i.e. casualties he cannot cover up); third, he relies on a significant constituency in the US ‘deep state’ (e.g. Zionists or the Miami Mafia) to back his adventures; and fourth, he is attracted by the prospect of plunder, resources such as oil he can steal from his target country. In his typical vulgar style, Trump has made no secret of this.

In the case of the Venezuelan intervention, leading to the kidnapping of President Nicolas Maduro on January 3, 2026, the tactic of ‘decapitation’ and intimidation or coercion seemed to work, as the remaining Venezuelan leadership caved in to Trump’s demands. While we do not yet know all details of this operation (both sides present self-serving and unreliable stories) we do know that, on the Venezuelan side, there was a betrayal of principle which has led to Washington effectively controlling the country’s oil industry and financial revenues, banning commitments the Caracas had with China (oil for credit) and Cuba (payment for the Cuban health missions) and even surrendering former political prisoner Alex Saab. This presupposes a level of corruption which short circuited organised resistance.

The Cubans have so far said little about this betrayal: (1) because the current Venezuelan leadership is putting a gloss on it, (2) because of the important role Venezuela played in support of Cuba this century and (3) because they were waiting on internal Venezuelan criticism. Now that criticism has emerged e.g. in the form of an essay by leading intellectual Luis Britto Garcia, who demands an examination of all the dangerous compromises made after January 3, 2026, adding “they intend to strip us of sovereignty, independence, natural resources, autonomy, rights, past, present, and future, in favor of an aggressive power that hates and despises us”. However, my friends in the Cuban Communist Party are horrified at the collapse of political will in Venezuela and cannot accept that these compromises were necessary, despite the pressures and lethal intimidation.

Cuban commitment to resist is one thing, but from Trump’s point of view, a Venezuelan style operation against Cuba might suit him well. Indeed, he hoped to get away with a similar operation in Iran, after what he was told by the Israelis would be a short bombing campaign, followed by a popular uprising. What he did not count on was the resilience and cohesion of the Iranian people and state, and the substantial and effective investment the Islamic Republic had made in its arsenal of asymmetric warfare.

With success in Venezuela followed by failure in Iran, Trump may be looking for some sort of compensation with Cuba, but how do conditions compare? One thing is to look at the logic of domination but, in each case, that has to be tempered with the logic of resistance. In Iran, the logic of resistance is prevailing. Furthermore, the bitter defeat at the hands of Iran may actually make Trump think twice before jumping into a new aggression against Cuba.

So, given the character and conditions of Cuba, to what extent could Trump expect to repeat an intervention which relies on the assassination or kidnapping of leaders and the installation of a compliant regime, with the help of Cuban traitors and the defusing of internal resistance? Further, to what extent does Cuba, weakened by a savage siege, retain its legendary capacity to resist and survive? The little island state does not have the resources or weapons of Iran, and its geography is very different, but it does have some other assets and is less likely to have its leadership purchased.

It is worth recalling that the crippling 12-year siege of Assad’s Syria did not by itself lead to the Syrian collapse of late 2024. Soldiers of the Syrian Arab Army (SAA) fought US-backed sectarian terrorist militia for many years on tiny salaries of perhaps $5 a month. However, from this writer’s conversations with experienced Syrian analysts, the collapse of the SAA (its failure to oppose the HTS offensive) was not due to soldier exhaustion but rather to the Qatari-Turkish enemy’s purchase of a large number of senior Syrian commanders, who remained in Syria to collaborate with the triumphant HTS militia. So siege alone does not guarantee "regime change".

Cuba does not seem similarly vulnerable to the purchase of corrupt commanders, and it has a very well established intelligence system (including a civilian network) which leaves far fewer chances that Havana will be surprised by infiltration and betrayal. The more than 600 US attempts to assassinate Fidel Castro did not fail by accident.

Terms of US capitulation to Iran presage new era for the region

Throughout the long history of US attempts to overthrow the revolutionary Cuban government, Cuban counter intelligence not only detected and thwarted assassination attempts but also infiltrated groups set up by the CIA and the NED, often assuming leading positions in those groups. This was detailed in two books: The Dissidents (2003, by Luis Baez and Rosa Miriam Elizalde) and The Confessions of Fraile (2003, by Percy Alvarado Godoy).

Even more importantly, the mass organisations built by the Cuban Revolution maintain strong links between the state and popular mobilisation. Organisation within the Committees for Defence of the Revolution (CDR), the Students Federation (FEU), the Federation of Cuban Women (FMC), the trade union federation (CTC), the Communist Party, as well as schools, health and disaster management institutions, ensures lines of communication and mobilisation critical to face an invasion. This includes radio links used, in the hurricane season, to advise and help organise public safety during tropical storms. That level of emergency organisation is said to best explain why hurricanes rarely kill in Cuba, unlike in other parts of the Caribbean. When it comes to high priority matters, Cubans can organise very effectively.

The link between the government and the people through mass organisations is critical in considering to what extent Cuba as a whole would follow through on its leadership themes (“death to the invaders”) and plans (war of the entire people). Decades of planning traps for invaders could make things very costly for even the best armed invasion force. Like Iran, Cuba has been preparing defensive strategies for decades. The US could seize some land in Cuba, but would face substantial casualties from the resistance. For much the same reason, Trump avoided any attempt at an invasion of Iran.

So what about the offsetting factors that help mitigate the current siege and allow Cubans to survive?

First, there is the culture of adaptation in face of shortages. Cubans are not a spoiled population with all the latest technologies, and they have (for example) trained thousands of doctors (Cubans and others) to save lives through human ingenuity and attention, without relying on technology. That is, they know how to live with shortages.

Second, the fuel crisis is offset to some extent by: (1) new refining capacity for Cuba’s heavy oil reserves (more difficult to refine and requiring substantial diluents), including those in offshore fields on the north coast which have recently been accessed from onshore drilling; (2) assembly and integration of Chinese solar panels into the national electricity grid, a large part of the sustainable energy plan, which feeds into the increased use of electric vehicles while also linking health centres and schools with solar power; (3) US plans to build a private sector political constituency, by selling fuel to private Cuban companies and embassies; it will be hard to quarantine such fuel supply, given the many urgent social needs.

Third, while Cuba has long been dependent on fuel and food imports, the recent crisis, like that of the 1990s, is helping drive initiatives in self-sufficiency, especially when the country’s main tradable assets (human capital in health and education missions) are blocked. Agricultural projects and sustainable energy projects, which have had limited success, now assume greater urgency.

Fourth, there is still a strong reserve of international goodwill towards Cuba, which supports the shipping of aid as well as diplomatic pressure to defend an island nation which has done so much to help many other countries with their health and education needs. Several countries are already shipping aid, and the Mexican president has said she will try to renew fuel supplies.

For Trump, Cuba does not offer quite such a strong incentive for plunder as did Venezuela, which has the world’s largest oil reserves (controlled by Washington for most of the 20th century).  Nevertheless, Trump associates in Gillon Capital seem to be taking over the Canadian firm Sherritt, which until recently had a large stake in Cuba’s nickel mining and exports. The older generation of Cuban exiles, the ‘Miami Mafia’, which has always backed US annexation of the island, remains part of the US deep state, but its influence has waned in recent times, especially as the new generation of Cuban emigrants maintain better relations with the island, both personally and politically. This mafia is today less influential than the Israelis, who drove Washington’s war on Iran.

To a predator like Trump, the logic of domination might suggest Cuba as a prize, the “ripe fruit” coveted by the US for two centuries and which has not yet fallen into the hands of any previous US president. The apparent success of the Venezuelan operation does offer hope for a similar scheme against the stubbornly independent island. Trump may be looking for compensation after his failure against Iran, and in any move against Cuba there is an extreme right Latin American faction of the deep state which would support him, including for a ground invasion, which would be necessary if no traitorous puppet clique emerges.

However, that faction is not so strong these days. Further, the bitter defeat inflicted on Washington by Iran may make Trump more risk averse; he must know that any ground invasion of Cuba would lead to mass casualties. He already has a difficult task ahead to sell the US retreat from the Persian Gulf as some sort of victory.

More importantly, any calculus of the logic of domination must also take into account the logic of resistance, a factor seriously underestimated in Washington’s war against Iran. Cuba has already demonstrated its capacity to survive extended siege and adapt to constant shortages. That includes the most recent reform proposals (allowing a substantial expansion of private business), which seek to undercut any political traction Washington may make in the Cuban population, as well as to improve conditions.

The chances of corrupting or purchasing the leadership are far less than they were in Venezuela. Cuba’s doctrine of large scale popular resistance is matched by a level of mass organisation and effective communications and coordination, as used when facing repeated natural disasters. Another invasion attempt - a foreseeable risk for the past six decades – has allowed Cuba to prepare and develop its pledge to confront any invasion force. They might be forced to cede some territory, but they are capable of inflicting serious casualties.

Most Cubans know the famous quote from 19th century independence fighter Antonio Maceo:

"Whoever tries to take over Cuba will bite the dust of its soil, drenched in blood, if he does not perish in the struggle."

Cuba is able to inflict such pain on any invasion force that Trump would once again be forced to retreat. In my opinion, stung by his miscalculations in the Persian Gulf, it is more likely he will not even attempt such foolishness.

The views expressed in this article are solely those of the author and do not necessarily reflect Al Mayadeen’s editorial stance.