Coercion Over Combat: The Future of Trump’s Strategy Toward Cuba

The administration of U.S. President Donald Trump has demonstrated a clear intent to reassert American influence throughout the Caribbean, viewing the region as a vital component of its broader national security strategy. As a result of this renewed focus, Cuba has re-emerged as a primary flashpoint. With Beijing and Moscow increasingly expanding their economic and strategic footprints in Havana, the island has transformed into a central theatre for great power competition involving the United States, China, and Russia. Viewing this foreign encroachment as a direct threat, Washington has intensified its rhetoric. Crucially, the administration has explicitly characterised Cuba as a “failing state”—a designation that highlights the island's severe internal crises and signals Washington's belief that proactive, decisive intervention is necessary to prevent further destabilisation on America's doorstep.

This expanding U.S. posture in the Western Hemisphere is driven by a deep-seated desire to consolidate regional control and push back against geopolitical rivals. It aligns seamlessly with the historical framework of the Monroe Doctrine, which has long asserted American dominance and rejected outside interference in the Americas. Against the backdrop of these escalating tensions, a critical strategic question arises: Is the United States becoming increasingly likely to pursue direct military intervention to resolve the Cuban issue, or will it maintain a strategy of maximum pressure—relying on coercive measures such as severe economic sanctions, diplomatic isolation, and political coercion—to advance its long-term objectives?

The United States has maintained a continuous strategic interest in Cuba since the 1890s. In 1898, the U.S. army helped Cuba gain its independence from Spain, but instead, the country has fallen into U.S. control until 1902. The following periods witnessed American direct and indirect intervention in Cuba, aiming to ensure its hegemony in the Hemisphere. The foundation for U.S. intervention in Latin America in general lies in the Monroe Doctrine, developed in 1823, which originally aimed to deter European interference but evolved into a justification for U.S. intervention in the hemisphere.

Over time, this doctrine has been repeatedly reinterpreted to legitimise intervention, especially during the Cold War in the 1960s, when Cuba aligned with the Soviet Union and the socialist government nationalised American assets, leading to a total U.S. embargo. Throughout the years, the American tools of pressure have shifted from military intervention to economic embargo, sanctions, excessive tariffs, and diplomatic isolation.

Currently, Trump seeks to isolate Cuba by blocking the main source of its oil – Venezuela – through control of the country and imposing tariffs on any country that supplies Cuba. Further blockading the Island from fuel and expanding sanctions in energy, finance, and business. The administration believes that causing severe engineered crises would pressure the Cuban government and ease American control over the Island. As a result, the country suffers from the shutdown of core public services, like hospitals, and crippled aviation, food shortages, and political pressure.

Trump has worked to assert American dominance in the Western Hemisphere, as seen in military action in Venezuela and statements about the acquisition of Greenland. Trump has expressed his interest in acquiring Greenland, citing national security and mineral wealth. While he authorised military action to capture President Nicolás Maduro.

These movements are described as the “Donroe Doctrine” or “Trump Corollary”, which refers to Trump’s second administration’s foreign policy towards the Americas and his desire to reassert U.S. dominance over the Western Hemisphere and limit external actors’ influence, such as China and Russia. This includes expanding military and naval presence, applying economic pressure on adversarial governments, and targeting regimes perceived as aligned with U.S. rivals.

Trump invokes security-based reasoning to justify U.S. dominance in the region. He portrays certain countries as sources of transnational threats, notably migration and drugs, that undermine U.S. security. This framing is then used to justify intervention, presenting U.S. involvement as necessary to mitigate these threats and prevent them from reaching the country.

Earlier this year, Trump set his ambitions on Cuba on many occasions. On January 29, 2026, the U.S. administration stated that the Cuban government poses an “extraordinary threat” to U.S. national security and foreign policy, and in response, the U.S. will impose tariffs on any country that supplies or sells oil to Cuba. On March 5, 2026, Trump said that it was next on his administration’s agenda.

Then, on April 13, 2026, the President hinted that the U.S. may “stop by Cuba.” Since then, he has been intensifying pressure on the Cuban government to push them to the negations table. The U.S. created a severe economic crisis through an oil blockade and other forms of embargo prior to taking military action.

Recent developments suggest a shift from strict containment toward more aggressive posturing. As the Western Hemisphere is increasingly treated as a sphere of U.S. dominance, the key question is whether the Trump administration would resort to a full-scale invasion of Cuba or whether there are alternative strategies instead.

A shift in U.S. strategic priorities could influence Washington’s behaviour toward Cuba in important ways. The Trump administration seeks to redirect its focus from costly overseas engagements toward the Western Hemisphere. Although Cuba presents a distinct political and security environment, it possesses a military institution that controls the economy and is deeply embedded in the political system. The Grupo de Administración Empresarial S.A. (GAESA) is considered an integral pillar of the Cuban regime and is therefore difficult to dismantle.

Similarly, the GAESA stands as the dominant institution at the core of Cuba’s financial and political system. Backed by the Cuban Revolutionary Armed Forces, it is estimated to control over 70% of the economy and 95% of the nation’s financial system, positioning it at the centre of national decision-making. Accordingly, dismantling the GAESA would represent a complex and challenging objective for the U.S. administration.

Also, people who fled Cuba before the revolution, including U.S. Secretary of State Marco Rubio’s parents, to Florida, U.S., are from the business owner class who feared losing their assets and opposed Fidel Castro’s communist government. This is reflected in Rubio’s persistent advocacy efforts for a regime change in Havana, mirroring the preferences of influential Cuban-American circles in Florida.

Meanwhile, the situation on the ground is different: with limited opposition and one-party rule, the Communist Party of Cuba (PCC) leaves very little space for a unified political force as an alternative option. While citizens residing within the country, wanting the hardships to end, oppose any U.S. military intervention and seek to defend their country’s sovereignty.

Moreover, military action is not the only political option available. Alternative forms of coercive pressure, including economic sanctions, diplomatic isolation, financial restrictions, and political pressure, may offer Washington a less costly means of achieving its objectives while avoiding the severe humanitarian, economic, and political consequences associated with direct military intervention.

Additionally, the costs of any military action against Cuba would be particularly asymmetric given the island’s geographic proximity to the United States. Any conflict could rapidly trigger large-scale migration flows toward the United States, causing regional instability and placing a substantial financial burden on the U.S. administration.

A direct U.S. military involvement in Cuba is unlikely due to high military, economic, and diplomatic costs, as well as the lack of a clear post-regime alternative. Rather than direct military action, the U.S. might prefer an economic deal that could define the future of American-Cuban relations.

There is no immediate strategic necessity for a military action, as Cuba doesn’t constitute an immediate or urgent military threat to the United States’ security, unlike its role during the Cold War. Moreover, Havana lacks the broader strategic weight that would justify the substantial financial and political costs of a military intervention. This imbalance between limited potential gains and high projected costs is likely to shape and constrain the trajectory of future U.S. policy toward Cuba.

In addition, evidence suggests that military operations are not always a controlled option, nor does it constitute a guaranteed outcome. On the contrary, it could trigger broader geopolitical instability or economic downturns. Furthermore, the apparent “quick win” in Venezuela shouldn’t be treated as a general model. Unlike Caracas, Cuba lacks a unified political opposition capable of governing in a post-regime scenario.

Besides, Cuba’s leadership is willing to negotiate economic and social reforms, including foreign investment from Cuban nationals, increasing tourism, releasing political prisoners, and migration. Nevertheless, they are unwilling to concede on core sovereignty, which is stepping down from power. In such a case, the U.S. administration has a higher probability of reaching a concession agreement than using military force.

Trump will be more likely to pursue an intensified economic strangulation, such as sanctions and trade restrictions, rather than a conventional military invasion. Seeking indirect democratisation efforts for a regime change, instead of direct confrontation, is due to his need for a “quick win” without the military risk. Moreover, a military invasion would lead to a huge migration flux towards the U.S., something that the administration seeks to avoid, particularly with its strict anti-migration policies.

The goal of intensifying economic pressure is not necessarily the immediate collapse of the Cuban government but rather to force Havana to reassess its cost-benefit analysis. By creating a severe economic crisis, the Cuban government will be faced with unbearable costs. Hence, Washington may seek to compel the Cuban authorities to negotiate from a position of weakness and on terms largely in favour to the United States. In this sense, sanctions and the oil embargo become bargaining tools rather than ends in themselves, allowing the US administration to offer a selective, gradual easing of sanctions in exchange for structural economic concessions.

The final situation could be defined by an economic agreement between the two governments, in which Washington could ease sanctions and foster investment in exchange for Cuba privatising state-owned enterprises to attract foreign investment, particularly American investment, notably in oil and mining. At the same time, the U.S. will allow Havana to buy its energy and technology while fostering a cooperation framework on the prevention of migration to the United States.

A dilemma appears in the implementation phase; GAESA is deeply embedded in the regime and difficult to dismantle. So, rather than dismantling the GAESA, Washington might tolerate its continued dominance, provided it becomes the institutional body responsible for managing foreign investments. In this case, privatisation is likely to take the form of joint ventures, minority foreign shareholding, or the liberalisation of specific sectors, rather than a complete dismantling of military-owned enterprises.

This agreement would make the Cuban economy more dependent on the United States than on what Trump perceives as “foreign influence” of China and Russia. The Trump administration may seek to replace the Russian and Chinese investments in Cuba with American and European investments in core areas such as energy, telecoms, tourism, and ports.

This potential trajectory would come into conflict with Rubio, who is currently leading negotiations with Cuban officials and advocates for Communist regime change in Cuba, conditioning economic development and investments with such change. Consequently, any shift from coercion to negotiation is likely to face resistance from within the Trump administration itself. It also has drawbacks on Trump’s approval rate with Cuban-American voters who believe that a US military action for regime change is the only option, disregarding an economic pathway.

In sum, although a direct military intervention in Cuba appears unlikely in the meantime, the situation raises broader concerns about the future of state sovereignty. The consequential shift lies in whether such actions would become more justifiable within U.S. strategic discourse under Trump, potentially normalising coercive approaches in relations between powerful states and those perceived as a “failing state”. Targeting states that diverge from U.S. interests and policy agendas risks eroding the principle of sovereignty as a foundational norm of the international system.

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