Abstract
U.S.–Cuba relations have entered their most confrontational phase in years, marked by a shift from sanctions-management to coercive geopolitical pressure. Since mid-2025, Washington has re-centered Cuba policy around national security, hemispheric control, energy interdiction, sanctions enforcement, and legal escalation. A clear example of this shift was seen in the National Security Presidential Memorandum (NSPM-5), reissuance in June 2025, in which a hardline framework that prioritizes restricting Cuban state revenue, supporting the embargo, limiting travel and financial channels, and treating engagement with Havana as conditional on U.S. strategic interests was restored. In addition, an executive order from January 29th, 2026, declared Cuba an “unusual and extraordinary threat”, transforming the policy by threatening tariffs against foreign countries that supply oil to Cuba, thereby converting Cuba’s energy dependence into a regional enforcement mechanism.
To sum up, the latest developments — Raúl Castro’s May 2026 indictment, an executive order with new sanctions on May 1st, the June 2026 OFAC designations of Cuban leaders and institutions, and a rare U.S.–Cuban military contact near Guantánamo Bay — suggest that Cuba is no longer treated only as a bilateral problem. It is now being folded into a wider U.S. strategy toward the Caribbean, Venezuela, Russia, China, Iran, and the hemispheric security. On one hand, Washington’s pressure campaign aims to reduce Havana’s strategic room for maneuver, deter third-country support, and raise the cost of Cuban alignment with U.S. adversaries. While on the other hand, Havana frames the campaign as a sovereignty issue and a pretext for a possible intervention on the island.
With all this in mind, there are three areas with an important geopolitical weight. First, the United States is using sanctions and energy restrictions not merely to punish Cuba but to reshape regional alignments. Second, the Caribbean is becoming an area of great-power denial, where Washington seeks to prevent Russia, China, Iran, and allied networks from using Cuba (or any other state in the region) as an intelligence, military, or diplomatic platform. Finally, the escalation could carry risks for both sides: it could trigger Cuban counter-alignment, deepen regional opposition to U.S. interventionism, strain relations with partners affected by extraterritorial sanctions, and elevate Guantánamo from a dormant sovereignty dispute into an operational flashpoint.
Introduction
The relationship between the United States and Cuba has been difficult since the victory of the Cuban Revolution in 1959, it has oscillated between containment, selective engagement, and attempts at normalization. Today, this relationship is a combination of Cold War-style regime pressure with 21st-century tools of financial enforcement, supply-chain coercion, counterterrorism designation, and regional military signaling. The U.S. NSPM-5 has restored a policy centered on the embargo, restrictions on transactions and travel, and the channeling of resources away from the Cuban state institutions. The shift is notorious, as the Obama-era normalization framework has been completely displaced already.
This recent change is not only ideological, but it also has a geopolitical background, instead. Washington now presents Cuba as a node in a wider strategic network that includes Russia, China, Iran, Hezbollah, Hamas, and U.S. adversaries in Latin America. In an executive order from January 29th, 2026, the White House declared that Cuban government policies and actions constituted an extraordinary threat to U.S. national security and foreign policy, citing Cuban ties with hostile states and non-state actors. The order also created a mechanism for imposing additional duties on products from any foreign country found to be directly or indirectly supplying oil to Cuba.
At this point, the role of oil and Cuba’s energy dependence on it should be highlighted, as the US has used it as leverage in the island’s current energy crisis. Cuba’s energy dependence has become a geopolitical pressure point. Washington has targeted not only Havana but also the external actors that keep the Cuban state functioning. The result is a form of secondary coercion that reaches beyond the bilateral embargo. It raises the cost for third parties — state-owned companies, banks, insurers, shipping operators, and foreign governments — of maintaining economic ties with Cuba. The May 2026 sanctions order and the June 2026 OFAC designations reinforced this logic by expanding the universe of sanctionable conduct to actors in the energy, defense, metals and mining, financial services, and security sectors of the Cuban economy.
At the same time, this hardening of U.S. posture reflects a broader hemispheric doctrine, and it is supported and stated in the 2025 National Security Strategy (NSS 2025). Several analyses and think tanks describe Washington’s renewed activism in Latin America (and the Caribbean) as a modernized Monroe Doctrine logic. In this modernized doctrine, the United States is reasserting dominance in the Western Hemisphere not only against extra-regional powers but also against regional governments perceived as aligned with those external powers. In this context, Cuba’s strategic value is magnified by its geography, its history of resistance to U.S. pressure, its intelligence and security relationships, and its symbolic position as the most enduring anti-U.S. government in the Caribbean and maybe in the whole region.
This analysis, therefore, will examine the geopolitical implications of the latest developments in U.S.–Cuba relations. The core argument showed that the confrontation is no longer just about sanctions or regime ideology; it is about hemispheric order, control over Caribbean strategic space, and the limits of U.S. coercive power in an increasingly multipolar environment.
From Embargo Management to Coercive Hemispheric Strategy
There are two official documents that changed and ended the Obama-era normalization strategy and converted the US-Cuba relationship into a coercive hemispheric strategy from the US towards Cuba.
The first one is the NSPM-5 policy, which marked the institutional foundation of the current confrontation. It states that U.S. policy will be guided by national security and foreign-policy interests, it seeks to channel funds toward the Cuban people and away from the Cuban government, also it supports the embargo, opposes international efforts to end it, and ensures that engagement advances U.S. interests. In summary, it converts Cuba policy from a narrow bilateral question into a test of Washington’s ability to discipline flows of money, travel, trade, information, and diplomatic recognition in the hemisphere.
The second is the January 29th, 2026, executive order, which elevated Cuba from an adversarial neighbor to a formal national-security emergency. This order accuses Havana of aligning with Russia, China, Iran, Hamas, Hezbollah, and other hostile actors; hosting military and intelligence capabilities; and supporting destabilizing networks in the Western Hemisphere. Whether all these claims are real or accepted by other states or not, what matters is that Washington has codified them as the legal basis for an economic and potentially strategic escalation.
For example, the oil-tariff mechanism is the most innovative part of the January order. In simple words, now Washington threatens countries that supply oil to Cuba, instead of simply sanctioning Cuban entities. This is important to highlight, because it creates a deterrent effect beyond U.S. jurisdiction. In other words, foreign governments and firms must now assess whether energy transactions with Havana could expose their exports to additional U.S. duties. In consequence, for Cuba, the implication means strategic isolation, while for third countries, it is a warning that Cuba has become a sanctions-risk environment comparable to other contested geopolitical spaces.
This approach also affects Cuba’s options for external balancing. Havana has traditionally used relations with Venezuela, Russia, China, Mexico, and other partners to offset U.S. pressure. But the current U.S. strategy targets the enabling infrastructure of that balancing: fuel, finance, shipping, mining, and banking. In addition, the June 2026 OFAC designations added President Miguel Díaz-Canel, Lis Cuesta Peraza, Alejandro Castro Espín, Raúl Alejandro Castro Calis, Manuel Anido Cuesta, and entities including MINFAR, the Committees for the Defense of the Revolution, ICAP, Amistur, and Minera La Victoria to the Specially Designated Nationals and Blocked Persons List (SDN list).
The designation of MINFAR and the sanctions exposure around GAESA, MININT, and MINFAR are especially significant. OFAC clarified that as of June 4, 2026, all three are blocked under E.O. 14404, and that non-U.S. persons — including foreign financial institutions — face sanctions risk for transacting with them or with entities they own by 50 percent or more. In short, these measures extend beyond targeting or punishing Cuban officials; they represent a broader effort to isolate Cuba’s state-controlled commercial network from the international finance system and increase the risks associated with doing business with it, in simple words, they are raising compliance risks for international financial actors.
The broader geopolitical significance of these sanctions is that they now operate as a mechanism of regional alliance discipline. The United States is not only seeking to influence Cuba’s behavior directly but is also signaling to third-country governments, financial institutions, and commercial actors that engagement with Cuba’s strategic sectors may carry substantial economic and regulatory risks. In this way, the sanctions extend beyond bilateral pressure and serve as a tool for shaping the behavior of external actors that maintain ties with Cuba. Of course, this has an extraterritorial logic that may deter smaller Caribbean or Latin American states, but it may also generate resentment among governments that view the policy as an infringement on sovereignty.
But also, another layer could be added, Guillermo Suarez’s analysis (here) of the terrorism designation argued that listing Cuba as a state sponsor of terrorism operates as a barrier to normalization and pushes Havana toward partners less acceptable to Washington. Keeping that in mind, the previous argument becomes more relevant now, because the harder Washington makes conventional economic engagement, the more likely Havana is to seek support through opaque channels, state-to-state barter, security cooperation, and non-dollar settlement mechanisms, or likely US rivals. In that sense, coercion may weaken Cuba’s economy while strengthening the geopolitical rationale for Cuban alignment with U.S. rivals.
Legal Escalation and Military Signaling
In May 2026, the US Department of Justice charged former Cuban president Raúl Castro and five co-defendants in connection with the February 24th, 1996, shootdown of two unarmed Brothers to the Rescue aircraft. From a legal perspective, this indictment revives a historic dispute in the US-Cuba relations. While from a geopolitical perspective, it targets one of the most emblematic figures of the Cuban revolutionary state, converting an unresolved historical grievance into a mechanism of political pressure that challenges the regime’s enduring claims to legitimacy and authority.
A Cuban top diplomat in Washington told the Associated Press that the recent move, together with the sanctions, have been interpreted in Havana as a pretext to persuade Americans to support military intervention in the Caribbean island. The same report notes that Cuban officials see parallels with U.S. actions against Venezuela and that the Trump administration has not ruled out military action while continuing to demand reforms. Therefore, even if direct intervention remains unlikely, the perception of a possible intervention has strengthened Cuba’s military preparedness and encouraged efforts to cultivate and maintain strategic alliances and shape more assertive diplomatic messaging by the Cuban government.
A different dimension to be added in the escalation is Guantánamo. On May 30th, 2026, Reuters, via Military Times, reported that the head of U.S. Southern Command, Gen. Francis Donovan, held a rare meeting with senior Cuban military officials at the perimeter of U.S. Naval Station Guantánamo Bay. Although the meeting was reported as focusing on operational security, force protection, safety, and military readiness, its significance extends beyond these technical concerns. Under normal or low-tension conditions, the engagement would be described as routine, but in the current geopolitical environment, however, it carries a greater strategic importance, demonstrating that both sides recognize the risk of miscalculations and escalations around an American military enclave on Cuban territory.
The geopolitical importance of Guantánamo is unique, as it is simultaneously a U.S. military asset, a Cuban sovereignty grievance, and could be seen as a crisis-management contact point. On one hand, the United States needs the base for regional military posture and migration/security operations. On the other hand, Cuba sees it as an illegitimate remnant of earlier U.S. domination. The recent perimeter contact suggests that both governments understand the base could become a flashpoint if sanctions escalation, military exercises, drone fears, or regional conflict spill into the Caribbean theater.
The U.S. approach also reinforces the integration of Cuba into Washington’s broader security strategy for Latin America. Officially stated in the White House’s January order, the US explicitly links Cuba to Russia, China, Iran, and non-state actors. At its core, the order aims to prevent rival powers from using Cuban geography, intelligence facilities, ports, or political networks that could challenge U.S. dominance near the American mainland or the Western Hemisphere in a broader scenario. From this perspective, Cuba’s value is not its economic weight but its strategic location, intelligence relationships, symbolic defiance, and potential to complicate U.S. regional policy and objectives.
At this point, the so-called “Donroe Doctrine” interpretation becomes relevant. The second Trump administration’s hemispheric approach as a more assertive adaptation of the Monroe Doctrine, focused not only on European interference but on any non-U.S. power operating in the Americas. In that framework, Cuba is not merely sanctioned because of its domestic governance; it is pressured because it is seen as an opening through which Russia, China, Iran, and anti-U.S. regional forces can gain strategic access and threaten US national security.
When combining these legal and military dimensions, there are risks and signs that can create escalation ladders even when neither side seeks war. For example, while sanctions may be intended as coercion short of force for the US, Cuba may interpret them as preparation for regime-change operations. Military contacts may be intended to prevent incidents, but they also underscore the proximity of armed forces. Another example is the indictment of Raúl Castro that Havana may read as a symbolic decapitation of revolutionary legitimacy. Taken together, these competing interpretations increase the risk that a routine patrol, a cyber incident, an intelligence allegation, or a confrontation near Guantánamo could acquire strategic significance far beyond its immediate facts or circumstances.
Regional and Global Implications
The U.S.–Cuba confrontation has implications beyond Havana and Washington. First, it repositions the Caribbean as a strategic chessboard. Cuba’s location gives it outsized importance in maritime routes, intelligence collection, migration management, and access to the Gulf of Mexico and Florida Straits. Therefore, a hardline U.S. policy signals to other Caribbean states that Washington intends to prevent the region from becoming a platform for extra-hemispheric competitors.
Second, this US policy will test the limits of extraterritorial sanctions. OFAC’s warning that non-U.S. persons face sanctions risk for dealings with GAESA, MININT, MINFAR, and their majority-owned entities creates compliance pressure worldwide. This can deter investment, shipping, insurance, and financial services connected to Cuba. But it also reinforces a broader global debate about the weaponization of the dollar system. For instance, countries seeking alternatives to U.S.-controlled financial channels may interpret Cuba sanctions as another example of why de-dollarization, alternative payment systems, and South-South finance are strategically attractive.
Third, the pressure campaign carried out by the U.S. may complicate its relations with Latin American and Caribbean governments that oppose interventionism even if they do not support Havana ideologically. For instance, if Washington is perceived as using energy deprivation, secondary sanctions, legal indictments, and military threats to pursue regime changes, governments that value sovereignty and non-interference may distance themselves from U.S. policy. This dynamic is particularly significant at a time when China and other powers are expanding their presence by offering infrastructure investment, financing, technological cooperation, and diplomatic alternatives without demanding political alignment with Washington.
Fourth, the campaign may unintentionally increase the strategic value of Cuba for U.S. adversaries. A highly pressured Cuba has incentives to deepen relations with states willing to defy U.S. sanctions or provide support through nontransparent channels. The January executive order itself identifies Cuba’s ties to Russia, China, and Iran as a threat; yet the pressure strategy may encourage Havana to rely more heavily on exactly those countries. This is the classic dilemma of coercive containment: pressure can weaken the target’s capabilities while strengthening its dependence on rival blocs.
Fifth, international criticism can undermine the legitimacy of U.S. policy. Calls by UN High Commissioner for Human Rights Volker Türk to lift sanctions on Cuba highlight how measures presented by the United States as national security tools may be viewed by others as coercive or punitive. This perception can give Cuba additional diplomatic leverage to mobilize support in the UN, CELAC, CARICOM, and the broader Global South.
At this point, it is important to highlight the Caribbean dimension. Cuba has historically invested in diplomatic relations with Caribbean states. Key examples include the early recognition of Cuba by Barbados, Guyana, Jamaica, and Trinidad and Tobago, as well as later reinforced through initiatives such as the CARICOM–Cuba summits. In this context, while many Caribbean governments depend on relations with the United States, they also value non-intervention and regional autonomy. Therefore, a coercive U.S. campaign against Cuba could generate quiet resistance or calls for restraint, especially if secondary sanctions affect regional energy, tourism, shipping, or banking networks.
From Washington’s perspective, however, the policy has a clear strategic logic. Cuba is seen as a small but strategically significant adversarial foothold close to U.S. territory. Its military, intelligence, and diplomatic ties with U.S. rivals are treated as security concerns, while its continued resilience as a defiant state is seen as a challenge to U.S. influence in the Western Hemisphere. Its connections to Venezuela and other anti-U.S. actors give it regional relevance beyond its economic size. The current U.S. strategy therefore aims to constrain Havana’s strategic options by limiting external support, isolating key sectors, pressuring third-party suppliers, targeting elite networks through sanctions or legal channels, and keeping military channels open to manage escalation risks.
In summary, the central question is whether this strategy can produce political change without generating strategic blowback. While negotiated concessions would be presented as a success in Washington, Cuban hardening, deeper alignment with rival powers, regional backlash, or an incident near Guantánamo could instead undermine the policy’s objectives. The most plausible near-term outcome is therefore neither normalization nor military escalation, but a prolonged coercive equilibrium in which sanctions, legal measures, energy constraints, and military signaling define the baseline relationship.
Conclusions
The recent phase of U.S.–Cuba relations is best understood as a geopolitical pressure campaign rather than a conventional sanctions dispute. Washington is deploying legal, financial, energy, and military instruments to reshape the strategic environment surrounding Cuba. In this context, the NSPM-5 has reestablished a hardline policy framework, while executive orders and sanctions issued in early 2026 have converted Cuba’s energy dependence into a mechanism of regional enforcement and expanded the sanctions designation architecture. In addition, the June 2026 OFAC actions targeting Cuban leadership and institutions, along with the indictment of Raúl Castro, have added a symbolic legal dimension to the campaign.
Geopolitically, there are also substantial implications. The United States is attempting to deny Cuba the external support that allows it to withstand pressure, especially from Russia, China, and other partners. It is also warning third parties that Cuba’s strategic sectors carry sanctions risk. This turns Cuba into a test case for extraterritorial economic coercion and for U.S. capacity to enforce hemispheric discipline in a multipolar world.
For Cuba, the strategic response is likely to combine resistance, diplomatic mobilization, military caution, and deeper outreach to non-U.S. partners. Havana’s claim that sanctions and indictments are a pretext for intervention may be partly rhetorical, but it is geopolitically consequential because it justifies defensive posture and external balancing.
For the Caribbean and Latin America, the confrontation revives the sovereignty-versus-hegemony debate that has shaped hemispheric politics for two centuries. If Washington’s pressure is perceived as reflecting a more assertive hemispheric strategy, it may weaken U.S. legitimacy even among governments that do not support Cuba’s domestic model. If, however, Washington can maintain pressure while avoiding military escalation and preserving diplomatic channels, it may succeed in constraining Cuba’s strategic partnerships without triggering a regional crisis.
Consequently, the most likely scenario is a continued escalation below the threshold of war. In practical terms, this would involve expanded sanctions, increased compliance pressure on foreign firms, intensified diplomatic contestation in international institutions, and sustained military deconfliction efforts around Guantánamo, all of which increase the risk of miscalculation. In a relationship where legal indictments, energy interdiction, military readiness, and regime-change rhetoric now interact, even a limited incident could become a hemispheric crisis. The central geopolitical question is therefore not whether U.S.–Cuba relations will normalize soon; they almost certainly will not. The question is whether both sides can manage a coercive standoff without turning the Caribbean into the next major arena of great-power confrontation.
References
