Awaiting Counterrevolution: Cuba Faces Inevitable Transformation with an Uncertain Outcome

There is every reason to believe that once the current round of conflict in the Middle East has concluded, or maybe even sooner, Cuba might become the next foreign policy priority for the US administration. This is indicated both by Washington’s mounting pressure on Havana and by statements by Donald Trump confirming that he views the Cuban case as politically advantageous while not requiring significant effort. In mid-March 2026, he spoke of contacts already underway with Cuba and of the possibility of action regarding the Caribbean island immediately ‘after Iran’, even entertaining the idea of a ‘friendly takeover’.

It is no coincidence that Latin America’s longest-standing left-wing dictatorship invariably finds itself in the spotlight of both Republican and Democratic US administrations. Cuba remains a historically and geopolitically charged issue, where memories of the 1962 missile crisis, repeated waves of mass emigration of Cubans to the United States, the particular role of Florida located just 90 miles from the island, and the broader issues of the unresolved legacy of the Cold War and the strategic security of the Western Hemisphere all intersect. For this reason, any acute crisis surrounding Havana automatically makes its way into the US domestic political agenda.

From exporting the revolution to struggling for survival

Following the 1959 revolution, Cuba rapidly evolved not merely into an island socialist state within the military-political framework of the Soviet bloc, but into an active foreign policy project. Beyond the attempted deployment of Soviet missiles on the island, which triggered the Cuban Missile Crisis, one of the defining episodes of the Cold War, Havana in the 1960s and 1970s sought to establish armed insurgent footholds across Latin America by supporting left-wing radical movements and guerrilla groups. It subsequently became an important actor in Soviet geopolitics and in proxy conflicts in Africa, notably in Angola and Ethiopia. This foreign policy expansion conferred a particular international weight on the regime. From 1960 to 1990, financial aid from the USSR to Cuba amounted, according to various estimates, to between $65 billion and $100 billion – a vast sum by the standards of the time.

The collapse of the USSR brought Cuba to the brink of systemic collapse. In the early 1990s, the country entered the so-called ‘special period’, marked by a sharp contraction in imports, chronic shortages of fuel, food and foreign currency, and a fall in GDP of roughly one third. It was at this point, between 1993 and 1996, that alongside intensified repression the first cycle of forced reforms began. The authorities legalised the circulation of the US dollar and the euro, expanded self-employment, authorised farmers’ markets, stepped up the development of tourism and opened selected sectors to foreign direct investment, including through a special agreement with Spain in 1994. Cubans often resorted to stopgap measures. In particular, to compensate for the shortage of motorised transport, over a million Chinese bicycles and around 60,000 three-wheeled cargo tricycles were purchased. Overall, these measures proved sufficient to stabilise the macroeconomic environment and to justify halting further market reforms out of concern for weakening party control (→ Thomas: Cuba: The Pursuit of Freedom).This was further reinforced by the strategic alliance concluded in 2000 between Fidel Castro and Hugo Chávez. For the next quarter century, Caracas became Havana’s principal external resource base. A barter scheme took shape: Cuba sent tens of thousands of doctors, teachers, technical specialists, as well as security and intelligence advisers to Venezuela, and in return received up to 80–100 thousand barrels of oil per day on preferential terms. At its peak in 2012, direct financial aid, subsidies and investments from Caracas amounted to $14 billion, equivalent to around 12% of Cuba’s GDP.

However, from the mid-2010s, this model began to unravel as Venezuela’s own crisis deepened and oil production declined significantly. Cuba once again faced chronic fuel shortages and was forced to seek ad hoc supplies from other partners, including Iran and Russia. Growing external economic stress coincided with Fidel Castro’s gradual withdrawal from power and the rise of his brother Raúl, who, at the height of the global financial crisis, initiated a second cycle of reforms. Between 2008 and 2011, the authorities cautiously updated the post-revolutionary model by leasing state land, further expanding self-employment, easing restrictions on the buying and selling of housing and cars, and attempting to reduce the excessively bloated public sector (its share of the workforce decreased during these years from 84% to 75%). These reforms, however, proved insufficient to sustain economic growth and still did not touch upon the political system: this was not a matter of liberalisation, but rather an attempt to reduce chronic inefficiency through a limited expansion of market relations (→ Mesa-Lago, Pérez-López: Cuba Under Raúl Castro).

At the same time, another trend emerged: key revenue-generating sectors of the economy were progressively concentrated in the hands of the military business conglomerate GAESA. Under Raúl Castro, GAESA assumed control of key state-owned businesses, including hotels, the banking sector, logistics and retail trade, and became the operator of between 40% and 60% of the island’s foreign exchange flows (→ Vidal: GAESA, the Invisible Elephant in Cuba’s Macroeconomic Stabilization).

An important external framework for the second cycle of reforms was the brief thaw under Barack Obama. In 2014–2016, Washington and Havana restored diplomatic relations, eased certain restrictions on travel, remittances and business contacts, and Obama’s visit to Cuba in 2016 symbolically strengthened the possibility of partial normalisation. For the Cuban leadership, this created expectations of increased international tourism, remittance inflows and investment, and more generally of a less restrictive international environment without relinquishing the Communist Party’s political monopoly. However, following the arrival of the first Trump administration, the rollback of détente, the return of sanctions pressure and the further reduction of Venezuelan support (oil supplies had, by this time, fallen by 50%) significantly narrowed the scope for gradual modernisation.

The third cycle of reforms began in the 2020s, amid the severe consequences of the pandemic, persistently harsh sanctions and the ongoing restructuring of the power hierarchy, institutionally enshrined in the new constitution. Formally, significant structural changes took place, including a separation of the powers of the president, prime minister and defence minister, previously concentrated in the hands of the Castro brothers. Symbolically, this marked the end of an entire historical era. In practice, however, the Castro family retained decisive control, with Raúl effectively preserving overall authority over the armed forces and assuming the role of éminence grise. In the economic sphere, the most notable steps were the unification of the currency and exchange rates from January 2021, the legalisation of small and medium-sized private businesses, and a cautious opening of the economy to capital from the diaspora. As a result, for the first time in decades, the private sector surpassed the state sector in terms of retail sales value. Thus, given the clear signs of a profound imbalance in the old model of reproduction, these measures have already gone beyond the scope of limited adaptation.

The exhaustion phase and the erosion of structural pillars

However, the current crisis has engulfed all key spheres of life on the island, from energy and finance to demographics and social structures, and calls for more decisive measures to reform the system. The processes unfolding in Cuba can be understood as the collapse of the welfare state. The distinctive post-revolutionary order, in which internal stability was ensured by a combination of authoritarian violence, ideological mobilisation, external subsidies and geopolitical rent, has begun to disintegrate. As long as these links held, the regime could endure prolonged stagnation, constantly dragging its feet and postponing reforms, yet remain remarkably resilient. Once all these foundations fractured and began to weaken simultaneously, a space for transition emerged.

Between 2019 and 2025, the Cuban economy contracted by more than 10%. Trade and fiscal deficits soared (reaching 13.5% of GDP). As a result, even according to official figures, inflation has not fallen below 25% in recent years, while international estimates put the real figure at around 70%. Since 2021, more than a million people have left the island, out of a total population of around 11 million. This represents the largest exodus since the revolution.

On the one hand, emigration has functioned for decades as a release valve for social and political pressure. The departure of some of the most discontented, economically active and mobilised groups has eased internal tensions. Thanks to remittances, family ties, cultural practices and hopes of returning, the Cuban diaspora in the US has become one of the key external resources for the system’s survival. Thus, remittances and parcels from the US, averaging between $2 billion and $4 billion annually in cash and up to $3 billion in goods, mainly for resale, during the 2010s, provided up to 35% of the resources needed to finance the Cuban economy and reached over 70% of the population. In terms of their significance, these flows often exceeded revenues from tourism and traditional export sectors, including nickel mining and tobacco production. They also significantly alleviated the pressure of sanctions, partially replacing those resources that the island’s economy could not generate independently. Another factor ‘undermining’ the effectiveness of American sanctions was the shift to food imports from the United States worth up to half a billion dollars annually and accounting for over 40% of all agricultural supplies from abroad. The state-managed agricultural model has led to a profound decline in domestic production. A country once specialising in sugar cane, with exports reaching around 8 million tonnes in 1980, now imports refined sugar from Brazil and the United States. Overall, agricultural production has fallen by 40%.

On the other hand,the migration valve remains effective only so long as the regime can combine population outflows with the preservation of basic governability. In recent years, emigration has reached such a scale that it has begun to undermine demographic reproduction, the labour base and the domestic market. It has ceased to function as a political safety mechanism and has instead become a factor of depletion.

Against the backdrop of acute fuel and financial pressures, with oil supplies to the island having effectively ceased since January 2026 as a result of the US blockade, and the tourism sector, once a key source of foreign currency, no longer generating meaningful revenue, the disintegration of basic everyday infrastructure has accelerated. In March 2026 alone, Cuba experienced three major power outages, including a nationwide blackout. Over the past four months, there have been five large-scale collapses of the energy system, accompanied by disruptions to the water supply. A strict fuel rationing system has been introduced. This is why the Cuban crisis now appears so profound: energy failures, shortages of fuel and food, and the chronic degradation of infrastructure are beginning to erode the most basic level of social functionality.

The crisis is no longer a temporary economic or social dysfunction. The state is losing its capacity to ensure the normal functioning of everyday life and is being forced to seek support beyond the confines of its previous model.

The longevity of the Cuban regime cannot be explained by any single factor, whether repression, the charisma of the revolutionary generation, external subsidies or the existence of loopholes around US pressure. It has been the product of a specific combination of factors, all of which have now either weakened or begun to work against the system.

Thus, for decades the regime drew on the original revolutionary myth, which eclectically combined anti-imperialism, nationalism, social justice and the defence of sovereignty in the face of a great power. The history of the revolution functioned as a political language through which sacrifice, deprivation and international isolation were interpreted and justified. Shortages could be framed as the price of sovereignty, external pressure as confirmation of historical correctness, and mass emigration as the flight of a ‘fifth column’. Today, this symbolic resource has all but dried up and is unable to mobilise younger generations, who counter the official slogan ‘Homeland or Death’ with the slogan ‘Homeland and Life’, which has become a political and cultural symbol of a new protest movement. The song ‘Patria y Vida’ became the unofficial anthem of the mass anti-government demonstrations of 2021, and participants in more recent protests continue to chant it as a deliberate inversion of the old revolutionary canon. In effect, the erosion of the system’s legitimacy has accelerated, with its continued viability now sustained largely by institutional inertia and ritualised loyalty.

The significance of Cuban elections as a managed form of political mobilisation and symbolic validation of the existing order has been definitively devalued. The 2019 Constitution retained the Communist Party’s status as the ‘highest guiding force of society and the state’, ruling out any form of party pluralism from the outset. The electoral process takes place under constant supervision by the so-called Committees for the Defence of the Revolution, operating in close coordination with state security and law enforcement bodies, and now serves not a mobilising but a disciplinary and supervisory function. In this respect, unlike many contemporary autocracies, the Cuban system lacks even limited electoral competition. This is an important consideration when assessing possible transition pathways.

The country is in urgent need of political de-escalation, which would entail the release of all political prisoners, an end to repression and the legalisation of political activity as such. According to estimates by human rights organisations, between 1,214 and 1,980 people are currently imprisoned in Cuba on political grounds. On 3 April, on the eve of Holy Week, Havana announced an amnesty for 2,010 people. It remains unclear whether political prisoners are among those released; of the 51 individuals freed in March with Vatican mediation, only some, according to available data, were political prisoners.

Another, now largely exhausted, source of the system’s resilience is geopolitical rent. None of Cuba’s current strategic partners, including Russia and China, appears willing to assume the kind of external patronage role once played first by the USSR, and then by Venezuela.

A further distinctive feature of the Cuban regime is that it manages not growth, but scarcity. This sets it apart from authoritarian modernisation models built on the promise of prosperity in exchange for political passivity. Cuban authorities have organised society around the distribution of shortages, fuel, electricity, basic goods, freedom of movement and access to information. Scarcity has thus become not only an economic condition but also a political technology. Managing scarcity reinforces dependence on the state, even as the state itself weakens. It reduces individual autonomy and constrains horizons of action, as everyday energy is directed towards survival rather than political mobilisation. Paradoxically, such weakness produces a particular form of resilience: poverty, fatigue and shortages undermine not only the legitimacy of the authorities but also society’s capacity for coordination. Yet this logic has limits. When scarcity begins to erode the basic infrastructure of life, it undermines not only social autonomy but the state itself. The regime loses its capacity to function as a reliable distributor of scarcity.

The current Cuban system can therefore be understood as a post-revolutionary order with a deferred transition, now entering a phase of exhaustion, yet still possessing sufficient institutional density to block or slow its own transformation. Systems of this kind often undergo especially protracted and contradictory transitions

On the threshold of transition

To understand the possible scenarios for Cuba’s transition, it is useful to attempt to define the nature of a regime that has already undergone several phases of post-revolutionary evolution. Contemporary Cuba fits neither the category of classical totalitarianism, nor that of a conventional military dictatorship, nor that of standard electoral authoritarianism. A more complex formulation is required: a late post-revolutionary patrimonial-bureaucratic authoritarianism of scarcity.

The Cuban revolution initially exhibited clear totalitarian features. It sought not only political control but a profound transformation of society, morality, culture, labour and the very nature of civic subjectivity. Contemporary Cuba, however, is no longer totalitarian in the strict sense. The regime no longer possesses its earlier mobilisational energy, transformative ambition or a credible vision of the future. It demands loyalty but can no longer generate enthusiasm; it retains an official communist doctrine that functions more as a ritual language than as a programme for political action. The concept of a post-totalitarian or post-revolutionary society is therefore more applicable. The original revolutionary matrix operates as a mechanism of symbolic inertia, justifying the preservation of a monopoly on power but no longer capable of generating a collectively experienced future.

Nor can Cuba be reduced to the model of a military dictatorship. The armed forces and security structures have played, and continue to play, a fundamental role, including in economic management. However, their dominance is embedded within a broader party-state matrix. The military is not an autonomous ruling body, as in the classic military regimes of twentieth-century Latin America, but one of the central pillars of the post-revolutionary order. Any future transition will therefore involve not a simple ‘return of the military to the barracks’, but a more complex redistribution of power within a deeply militarised party-state apparatus.

A key characteristic of the late phase of the Cuban revolutionary regime is its patrimonial logic. Formally, Cuba retains the characteristics of an institutionalised party-state system, yet in practice access to power, resources and economic opportunities is determined not by impersonal procedures but by integration into networks of political patronage, personal loyalty and informal access to decision-making centres. Under such conditions, the bureaucracy becomes a channel for politically mediated privilege.

This feature is particularly important in the context of a future transition. Patrimonial-bureaucratic regimes rarely collapse along the lines of ‘freedom versus dictatorship’. More often, conflict unfolds around who will gain control over the new economic space, who will inherit the most profitable sectors of the old system, what security and property guarantees will be extended to incumbent elites, and how political monopoly will, or will not, be converted into post-revolutionary economic dominance. In other words, the central question is not only whether a transition will occur, but who will appropriate its political and economic outcomes.

Today, transition appears more likely than at any previous point. Younger generations no longer operate within the paradigm of 1959; their political language, as reflected in the character of mass protests, is built not around revolutionary sacrifice but around the idea of a normal life, dignity and a future. The role of the diaspora is expanding, not only as a familial and financial resource, but also as a political and symbolic external ‘Cuban world’. The growth of the private sector is reshaping internal patterns of dependence: society increasingly requires rules that the old regime cannot provide, predictability, property protection, contract enforcement and normal connectivity with the outside world. The expansion of these demands does not in itself guarantee transition, but it makes it more likely.

Among the opponents of change are, first and foremost, the party and state elite, who fear losing their monopoly over defining what is permissible. The security apparatus is concerned about potential retribution for repression, including lustration and the loss of immunity. The distributive bureaucracy and lower-level administrative structures are wary of the collapse of established modes of existence before new ones emerge. Finally, the ideological core perceives a deep transition as a form of capitulation to the outside world.

The potential coalition for change remains heterogeneous and far less organised than the entrenched ‘old regime’. It includes, first, the private and semi-legal non-state sector, which employs 1.6 million people out of a workforce of approximately 4 million. At the same time, the US has already begun to export fuel on a selective basis to this sector, seeking to support independent economic niches rather than the state itself. Second, there is the diaspora, which may gradually become involved in the country’s reintegration. Third, elements of the technocratic apparatus and certain economic groups within the system are potential participants. Fourth, broader segments of society are now engaged, for whom the issue has become one of basic normality, access to electricity, medicines and transport, and the ability to earn a living without constant scarcity.

However, in the Cuban case, should a political window for change open, the question of property will become particularly acute. For this reason, any transition is likely to be accompanied by the risk of nomenklatura or security-driven capture of the process itself. Following the 1959 revolution, assets belonging to US companies and private owners were confiscated, and this issue remains unresolved. In 1996, the United States adopted the Helms–Burton Act, which not only codified the embargo, removing it from presidential discretion and placing it under congressional authority, but also established a legal framework for property claims. Title III of the Act allows US claimants to bring lawsuits against those benefiting from confiscated property. In 2019, Donald Trump ended a long-standing suspension of this provision, turning such litigation into a tangible risk. The US Supreme Court is already considering cases involving Exxon and Havana Docks, with billions of dollars in potential claims at stake. This means that any Cuban transition will inevitably confront not only the political question of ‘who governs’, but also the question of ‘who owns’.

At this point, an important crossroads emerges. If property issues take the form of a comprehensive restitution drive, resistance from incumbent elites and the security apparatus is likely to intensify sharply. If, conversely, a transition seeks to bypass the issue of confiscations altogether, it will face legal and political constraints from the United States, given that the embargo cannot be lifted unilaterally by the executive. This renders the Cuban transition inherently more complex than it may initially appear. For this reason, the principal line of conflict is unlikely to run simply between ‘regime’ and ‘democracy’, but rather between two competing strategies: a managed mutation of the existing order and a genuine transition involving the dismantling of the party-bureaucratic monopoly, new forms of legitimacy and the resolution of property disputes.

Transition: scenarios and external actors

In the circumstances described above, some form of regime transformation appears absolutely inevitable today, and the question is merely which scenario will unfold. The first possible scenario is a controlled change from above. The regime recognises the limitations of the old model but attempts to save itself through partial economic opening, diaspora capital, external deals and minimal de-escalation, while retaining the principle of political monopoly.

The second scenario is a negotiated, or pact-based, transition. Elements of the old elite, new domestic actors, the diaspora and external mediators reach a multi-level agreement: first stabilisation and de-escalation, then the dismantling of monopoly power, followed by market opening, and only thereafter the establishment of a new constitutional and electoral framework. This is the most productive, but also the most politically demanding, scenario. The third scenario is a protracted crisis-authoritarian drift. The crisis persists, the regime does not collapse, external arrangements merely alleviate peak pressures, the diaspora is used as a resource but not incorporated as a political actor, and institutional re-foundation is deferred. This is one of the more likely outcomes if neither domestic nor external actors prove willing to engage in a deeper pact. The fourth scenario is a crisis rupture. The convergence of energy collapse, social exhaustion, elite fragmentation and external pressure disrupts the existing equilibrium. Transition accelerates, but becomes more volatile and less predictable.

The main question, therefore, is not whether the transition will occur as such, but who will shape its political form and in what sequence, including which external actors may push Cuba towards one trajectory or another?

The experience of 2014 demonstrates that the most significant breakthrough in United States–Cuban relations during the Obama presidency was prepared through discreet channels in Canada and the Vatican. The role of specific participants in such a process is also significant.During the period of Obama-era détente, an important behind-the-scenes role was played by Alejandro Castro Espín, son of Raúl Castro, a colonel in the interior ministry and one of his closest advisers on security matters. His influence derived not from formal diplomatic status, but from a combination of familial proximity, the trust of the security establishment and direct access to decision-making centres. Current informal contacts are reportedly linked to Raúl Castro’s grandson, Raúl Guillermo Rodríguez Castro, a former bodyguard to his grandfather and a figure situated at the intersection of the family circle, the security apparatus and the military-economic network of GAESA. Such intermediaries may act as guarantors for the old power structure. For that very reason, however, they are unlikely to become public figures in a post-Castro Cuba. Their value lies in their access, confidentiality and trust, rather than in any potential political role in shaping the new order.

The Vatican remains one of the few actors with a proven track record of acceptable mediation with Havana. In January 2025 and March 2026, Cuba released 553 and 51 prisoners respectively under arrangements facilitated by the Holy See. This recurring pattern suggests that the Vatican continues to function as a humanitarian and political channel through which the boundaries of the possible can be tested. This role has acquired additional significance under the first American pope, Leo XIV, who retains Peruvian citizenship.

Russia’s role today is primarily political and symbolic, rather than system-defining. Moscow has repeatedly indicated its intention to continue oil supplies to Cuba and its readiness to provide other forms of assistance. Clearly, the Kremlin seeks to preserve Cuba as a symbolic anti-American foothold, but its capabilities are limited. On 31 March, the Russian tanker ‘Anatoly Kolodkin’ delivered 730,000 barrels of oil to Cuba, marking the first major shipment in three months. According to expert estimates, this volume will be sufficient to meet the island’s minimum needs for approximately 10 days. This is revealing. Russia may use the Cuban crisis as a bargaining chip in its geopolitical dealings with Washington and as a demonstration of anti-sanctions solidarity, but it lacks the resources to sustain the regime in any meaningful way.

China appears to be a more consequential actor in structural terms. Beijing has gradually displaced both Moscow and Caracas as Cuba’s principal external partner. In the past year alone, China financed 55 investment projects in Cuba and supplied solar panels, components and some fuel. Beijing’s interest in Cuba extends beyond symbolic alignment to more pragmatic considerations, including energy, infrastructure, credit and surveillance technologies. For this reason, China is unlikely to favour a sudden or disorderly transition. Whereas Russia may contribute to prolonging the crisis through political support and limited energy deliveries, China is better positioned to shape the form of transition, supporting a scenario of managed mutation and resisting outcomes that would sharply reduce Havana’s dependence on Chinese engagement.

The role of transactional geopolitics, as practised by the current US administration, appears ambivalent when projected onto the transition scenarios. On the one hand, a transactional approach favours managed exchanges over systemic transformation, since the latter are difficult to guarantee and even harder to justify domestically. As a result, it often constrains the depth of change and favours the first and third scenarios, managed mutation and prolonged drift. It allows the existing order to persist through concessions without altering its foundations. On the other hand, transactional geopolitics can also act as a catalyst for political processes. It can open channels of de-escalation without which deeper transition would be impossible: discreet negotiations, partial guarantees, prisoner releases, limited energy arrangements, coordinated steps on migration and the testing of the old apparatus’s responsiveness to concessions. In this sense, the issue is not transactionalism per se, but whether it becomes the governing logic of the process or merely its initial diplomatic stage.

It is in this context that the role of US Secretary of State Marco Rubio takes on particular significance. His position on Cuba cannot be reduced to that of a conventional bureaucratic actor. Rubio is the son of Cuban immigrants, and this biographical dimension is integral to both his political identity and his perception of the Cuban regime.

On the one hand, Rubio may be one of the few American policymakers capable of combining pressure with an understanding of Cuban sensitivities. He is acutely aware of the real cost of concessions for the incumbent regime, the importance of the diaspora, and the emotional weight of sovereignty and exile in the Cuban context. In this respect, his involvement could facilitate a shift from a blunt rhetoric of regime change towards a more calibrated architecture of managed or negotiated transformation. On the other hand, the personal and symbolic resonance of the Cuban issue may incline him towards a more hardline and ultimately more transactional approach. In any case, Cuba represents for Rubio a potential legacy-defining project. If, with his involvement, a managed shift can be achieved without triggering mass migration, direct military intervention or humanitarian collapse, it would constitute a major political success and strengthen his prospective presidential credentials. Conversely, if pressure and transactional bargaining lead only to further destabilisation, energy shortages, chaotic migration or a partial and disordered transition without a new institutional settlement, he risks becoming personally associated with failure.