A Squeeze Without Precedent: The Trump Administration’s Cuba Campaign and Havana’s Strategy of Survival
Return to Maximum Pressure
When President Donald Trump took office in 2017, the steady thaw in U.S.-Cuba relations that had begun under his predecessor came to an abrupt halt. What followed was not simply a reversal of open economic engagement but a deliberate, systematic escalation designed to isolate the island nation once more. By the final year of the administration, the United States had deployed what many observers describe as the most intense pressure campaign against Cuba in decades. It was a coordinated wave of sanctions, diplomatic restrictions, legal threats, and political rhetoric aimed at squeezing Havana from every direction. The Cuban government, however, has responded with a phrase that has become a familiar refrain among its leadership: resistir, or to endure. According to official statements from Havana, the strategy is not to attempt a diplomatic breakthrough or to seek a negotiated easing of tensions, but to simply wait out the storm. The question is whether such a strategy is feasible in the long run, especially as the island faces one of its most severe economic contractions in recent memory. The renewed confrontation has revived the ideological battlefields of the Cold War, even as the world around both nations has shifted dramatically. There is no shortage of historians who note that Washington has tried this approach before. Yet the current combination of tools — drawn from Treasury, the State Department, and the White House itself — represents a more totalizing effort than many have seen in a generation. For Cuba, the message from Washington is unmistakable, but the response from Havana is a quiet, patient stubbornness that has characterized its politics for decades. Endurance, in this context, is not just an outward talking point; it is a survival road map, grounded in the conviction that time and history are ultimately on Cuba’s side.
A Tightening Noose: Sanctions, Lawsuits, and Travel Bans
The mechanics of the Trump administration’s assault on Cuba were multi-layered and carefully orchestrated. Among the most consequential moves was the reimposition of the full embargo through executive measures, which rolled back Obama-era access to banking and finance. Another significant action was the activation of Title III of the Helms-Burton Act, allowing American citizens and companies to sue foreign businesses operating on properties that had been expropriated by the revolutionary government. This was not just a legal detail; it sent a chilling effect through the international investment community. Foreign firms, especially those from Europe, suddenly had to weigh the risks of doing business in Cuba against the possibility of costly litigation in U.S. federal courts. The message was clear: if you trade with Havana, you will face consequences in Washington. Travel restrictions, too, were tightened considerably. Commercial flights from the United States to Cuban destinations were suspended, a measure that struck hard at visitors and family connections. Remittances, which had long served as a lifeline for ordinary Cubans, were sharply curtailed, particularly those sent to state-linked enterprises or military-affiliated officials. Cruise ships, once a welcome speaker of economic opportunity and a visible symbol of rapprochement, no longer docked at Cuban ports. The practical impact of these measures was felt immediately. The Trump administration also returned Cuba to the list of State Sponsors of Terrorism in January 2021, a designation that carries enormous symbolic and political weight. Although the move was largely criticized as one of the administration’s final gestures — announced amid the chaos following the Capitol insurrection — it has had durable legal consequences, including further restrictions on international banking transactions. For the Cuban government, however, these measures did not come as a shock. Officials in Havana had long anticipated a darker turn in U.S. policy, and the administration’s moves were seen as a confirmation, not a surprise. The broader political goal was to force a breakdown of foreign investment in Cuba and to weaken the state’s hold over its citizens, with the ultimate hope of prompting domestic unrest and political upheaval. But the Cuban leadership, acutely aware of the playbook, prepared for the siege by consolidating the state’s grip and shoring up its control over the economy.
An Economy Under Siege
The cumulative impact of these measures, when combined with the catastrophic effects of the COVID-19 pandemic, created the kind of economic storm Cuba has not experienced in decades. The island’s GDP contracted sharply, tourism evaporated, and sugar and tobacco exports were hindered by both weather and systemic challenges. Even before the pandemic, Cuba was walking a tightrope, burdened by Soviet-era infrastructure and a struggling single-party economy. The farm sector was strained, and chronic shortages of food and medicine became part of daily life. But the confluence of U.S. pressure and the global health crisis pushed the island to the edge. According to reports from international financial institutions, Cuba’s foreign currency reserves were depleted, and its ability to import essentials — from wheat to vaccines — was severely compromised. The black market grew stronger while the state-run distribution system became increasingly unreliable. By the summer of 2021, the frustrations of ordinary Cubans broke into public view, with protests erupting in Havana and other cities. Demonstrators carried signs demanding basic necessities and, in some cases, political reform. The Cuban government attributed the unrest to U.S. blockade and imperial aggression, while Washington blamed the unfinished nature of Cuba’s political and economic system. The humanitarian reality is arguably the most troubling aspect of the current confrontation. The pain is borne not by political elites but by low-income workers, the elderly, and families who depend on remittances from relatives overseas. The Cuban state’s response has been a careful balancing act: acknowledging hardship while maintaining a narrative of resilience. There is talk of new economic reforms, small openings to private enterprise, and a growing role for local currency. Yet the government is wary of moving too quickly, fearing that any relaxation of control could lead to unintended political consequences. The ability to buy foreign goods has become a privilege of the few, while the majority waits in lines that stretch for hours. In this environment, endurance is not merely a political slogan; for many Cubans, it is the central reality of daily life.
Havana’s Strategy: Endurance Over Surrender
Cuban officials have stated plainly that their plan is to outlast the pressure campaign. In public appearances, President Miguel Díaz-Canel and other leaders have frequently invoked the island’s history of resistance, pointing to the blockade imposed after the 1959 revolution and the difficult years after the collapse of the Soviet Union. That period, known in Cuba as the “Special Period,” brought severe shortages and widespread hunger, yet the revolutionary government managed to stay in power. For Havana, the current crisis is, in a sense, a familiar war. The economic insulation and state-centered planning that often seem inefficient during normal times become survival mechanisms during siege. The government has also pivoted its diplomatic attention toward alternative allies. China and Russia have deepened their economic and political ties with Cuba, offering credit lines and energy support. Cuba has also strengthened relationships with other Latin American governments that are less dependent on U.S. policy, such as Venezuela, Nicaragua, and Bolivia. In these broader alliances, Havana finds both economic support and, importantly, a rhetorical platform to counter U.S. narratives. At the same time, Cuba has been far more receptive to foreign investment in select sectors — such as renewable energy, tourism infrastructure, and pharmaceuticals — particularly from European and Canadian firms that are willing to pay the price of doing business with the island despite the U.S. threat. The key strategic move has been to maintain a kind of controlled austerity. Ration books, food deliveries, special distribution centers: these are all mechanisms designed to ensure that basic goods reach the population in an equitable, if insufficient, manner. The regime is acutely aware that hunger is a destabilizing force. Thus, patience becomes a political weapon. The idea is not to show rapid results in the marketplace, but to convince ordinary Cubans that survival is possible and that the revolution, however imperfect, remains their best guarantee of national sovereignty. The endurance strategy is also deeply rhetorical. It frames the conflict as one of David against Goliath, with Cuba standing in for the dispossessed, the Global South, and the historically oppressed. This narrative resonates at home and in many corners of the international community, where the United States’ policy of unilateral sanctions is widely seen as outdated and counterproductive.
Politics at Play: Miami, Exiles, and the Next Administration
One cannot fully understand the Trump administration’s Cuba policy without examining the domestic political landscape in the United States. For decades, Cuban-American voters in Florida have wielded significant influence in presidential elections, and Trump’s hardline stance was aimed squarely at this constituency. The policy was not only ideological; it was electoral. By tightening the embargo and imposing new sanctions, the administration solidified support among voters who remain deeply skeptical of any engagement with the Castro revolution and its successors. The careers of Republican advisors in Florida politics, with their carefully crafted anti-communist rhetoric, reflected a strategy that linked foreign policy with domestic electoral gain. But the political calculus extended beyond the exile community. The brinkmanship was also designed to burnish a broader image of strength, particularly to conservative audiences who saw crime and political repression in Cuba as unacceptable. The effect, however, has been to lock American policy into a much narrower path. When the Biden administration took office, there were expectations that the earlier detente might be restored. Yet those expectations were quickly tempered. Biden chose to maintain most of the sanctions, citing the Cuban government’s human rights record and the need for leverage. This continuity, while perhaps disappointing to some progressives, was understandable given the political constraints of a divided Congress and the influence of moderate Republicans in South Florida. Still, the continuation of Trump-era policies has not produced any discernible shift in Cuban behavior. Havana remains as intransigent as ever, and U.S. officials seem to have run out of imaginative approaches to achieve regime change without directly using military force. Meanwhile, the Cuban government has adopted a policy of intransigence toward Washington, refusing to negotiate under the threat of sanctions. This diplomatic stalemate, which began under Trump and continues under his successor, appears likely to persist well into the current decade. The two nations remain trapped in an endless cycle of provocation and response, with the heaviest burden falling on ordinary civilians who have no direct say in the policies of either capital.
A Test of Patience With No Clear Finish Line
As the pressure campaign continues, there is a growing sense that this is not a chess game that can be decisively won by either side. For Washington, the tools of economic coercion have their limits. The globalized economy offers too many alternative routes and loopholes for a nation under siege to be completely starved of resources. For Cuba, the strategy of endurance is similarly fragile. The patience of a people faced with shortage and limited opportunity cannot be assumed to be infinite, and the regime knows that it must offer some meaningful improvement in the quality of life to maintain legitimacy. There are signs, however tentative, of new internal economic partnerships with the private sector, and an acknowledgement that the state cannot produce and distribute everything alone. Yet these reforms remain carefully controlled, and the government remains suspicious of independent political organization that might follow from economic opening. The struggle has also shifted to the international arena. In recent sessions of the United Nations General Assembly, the vast majority of member states voted in favor of a resolution condemning the American embargo on Cuba, a symbolic but significant rebuke. The Biden administration has dismissed these votes as political theater, but the repeated global opposition underscores the isolation of the United States on this issue. Still, no international pressure has yet been sufficient to alter Washington’s course. Cuba, meanwhile, continues to wait. Its leadership draws on the myth of resistance, recalling the Cuban Missile Crisis, the Bay of Pigs, and the fall of the Soviet Union. It is a story that says: we have been through worse, and we will find a way through this, too. Whether that will prove to be true is uncertain. The island’s economic model is undeniably strained, and the young people who would like to build a future are often the ones most tempted to leave. The exodus of doctors, engineers, and artists to Europe or the Americas strips the country of its human capital and its hope. The long-term danger is that the Cuban state, while surviving politically, may lose the very people it claims to represent. The pressure campaign, then, has created a standoff between an eagle and a hummingbird — the eagle patient in its power, the hummingbird desperate in its endurance. For ordinary Cubans, caught in this geopolitical collision, the immediate future holds little more than waiting, rationing, and hoping that the next sunrise brings a temporary calm. In the halls of power in Havana, the official message remains one of pride, defiance, and endurance. Only time will tell whether that endurance will ultimately be remembered as a strategic success or a tragic struggle. For now, all the island can do is hold on, while the world watches and wonders which side will blink first.
