A fortnight ago, former Venezuelan dictator Nicolás Maduro and his wife, Cilia Flores, appeared unfazed in a New York courtroom, an uneventful start to what is expected to be a lengthy legal process following their dramatic capture on 3 January. President Donald Trump, meanwhile, boasts about the cooperative interim government of Delcy Rodríguez and claims that ‘Cuba is next’, suggesting a Caribbean sequel to his South American ‘decapitate and delegate’ operation.

Trump has found his archetype in Caracas and identified his legacy initiative in Havana. Venezuela stands as both the model for regime change and lynchpin for America’s reordering of the Western Hemisphere. Cuba, in contrast, presents a prized regime-change candidate but a far greater challenge. Indeed, 12 of Trump’s predecessors failed to dislodge the Castro regime despite a nuclear standoff and a codified embargo.

Successfully changing the Cuban and Venezuelan governments is crucial for cementing Trump’s hemispheric vision, removing the  long-standing obstacles to advancing US regional interests. But here lies the dilemma for Trump: the tension between achieving quick stability and ensuring an enduring democratic transformation.

Since Operation Absolute Resolve in early January, the Trump administration’s bid to construct an ‘Americas First’ hemispheric order has materialised further. In design, it aims to forge a secure hemisphere by wielding US power both to eradicate transnational criminal organisations and to discipline rogue regimes. In practice, it means an American-led regional partnership premised on combating crime, pursuing reciprocal trade, reducing irregular migration and extirpating the malign influence of China, Russia and Iran.

The order envisaged in Americas First encompasses a paradigm shift in national security policy. Waging an aggressive military campaign against drug cartels and gangs designated as ‘foreign terrorist organizations‘ is the key pillar to the ‘Donroe Doctrine’. Under Trump, the law enforcement-only strategy came to an end, while the war against narcoterrorism rages.

In the Western Hemisphere, US military and intelligence agencies have significantly expanded their operational role in battling transnational criminal organisations and hostile states. Over the last 14 months, the United States has engaged in a vast array of actions against them: removing Maduro, conducting strikes on narco-laden vessels, seizing sanctioned oil tankers, increasing its military presence and deepening security cooperation with countries across the region.

In doing so, the Trump administration has orchestrated a multi-tiered diplomatic and defence partnership known as the Shield of the Americas. A political-level grouping of 13 countries – including the US, Argentina, Panama and the Dominican Republic – forms its core, comprised of those that attended the inaugural summit on 7 March in Doral, Florida. Nested within this umbrella initiative is the Americas Counter-Cartel Coalition, a Department of War-led operational alliance with 18 nations to coordinate military, intelligence and law-enforcement actions against transnational criminal organisations.

Such a US-dominated configuration entails a coalition of pro-American governments that use military force against narco-criminals and embrace Washington’s commercial diplomacy while spurning China’s advances. The ebbing of the Pink Tide has given rise to governments eager to meet Washington’s demands. The intractable nature of transnational crime and the lack of regional security has driven Latin American leaders to accept Trump’s escalatory approach.

As conveyed in the 2025 National Security Strategy and the 2026 National Defense Strategy, Trump’s framework for hemispheric security features an old conception of homeland defence and a new impetus for exercising the full spectrum of US power. Venezuela and Cuba fit within the former and are subject to the latter.

On 5 March, at the US Southern Command headquarters, Secretary of War Pete Hegseth informed Latin-American attendees at the inaugural Americas Counter-Cartel conference that the Trump administration had reframed America’s zone of strategic interest in the hemisphere.

Trump, Hegseth observed, considers the homeland perimeter to encompass ‘Greenland to the Gulf of America to the Panama Canal and its surrounding countries’. The US shoulders chief responsibility for the areas above the Amazon rainforest and the Andes mountains; below, Latin American partners must share the burden. The idea of ‘quarter-sphere defense’ has prevailed in the Pentagon, but the ‘Greater North America’ concept does not exactly offer ‘a new strategic map’. Rather, Trump revived Franklin Delano Roosevelt’s concept of hemispheric defence, which developed out of FDR’s ‘Good Neighbor Policy’ and was consolidated in the run-up to the Second World War.

FDR was keen to use military force to defend the Western Hemisphere against the outside Axis aggressors, much as Trump now uses it against internal threats to Greater North America. ‘The heart of our agreement’, Trump announced at the Shield of the Americas summit, ‘is a commitment to using lethal military force to destroy the sinister cartels and terrorist networks once and for all.’ The nature of the threat has changed, but the rationale remains the same: the US is prepared to exercise military power throughout Greater North America to defend the Western Hemisphere as its vital security perimeter. Military action against narco-criminals intertwines with the Trump administration’s efforts to change regimes.

Deterrence and compliance are the watchwords of the US president’s policy, and Venezuela is the acid test. Trump’s Venezuela policy reflects a theory of coerced regime management, aimed at delivering democratic restoration through a three-phase plan of stabilisation, recovery and transition. Yet this framework faces the perils of expectations, complacency and time.

The interim Rodríguez government cooperates with the Trump administration, but the Chavista repression mechanisms remain mostly intact. Rodríguez revamped the executive branch and reshuffled military commands, but her personnel adjustments only reinforce her grip on power. While hundreds of political prisoners have been released under conditional amnesty, hundreds more languish in detention. Rodríguez has submitted monthly budgets to the US and enacted oil and mining reforms, yet Venezuela’s economy has not improved and inflation runs rampant. Support for María Corina Machado’s opposition movement stands strong, but a firm election date does not loom. America wields considerable leverage over the Venezuelan state, but international crises and domestic politics cut against it in the near-term. The groundswell of hope after Maduro’s ouster persists, but aspiration may transform into explosive frustration.

Despite the warning signs, tentative progress justifies cautious optimism.

The US has begun rejuvenating Venezuela’s oil sector, with companies like Shell seeking greater investments. Venezuelan crude oil now flows into American Gulf Shore refineries before being sold on the open market. The profits, in turn, enter US Treasury accounts for distribution to the Rodríguez government. As the Venezuelan economy opens, foreign investors are warming up to the risky endeavour of re-entering sectors.

Incremental steps to rekindle diplomatic relations and rebuild civil society are also underway. The headquarters of Machado’s Vente Venezuela party re-opened in Caracas around the same time as the US returned to its shuttered embassy after a seven-year closure. High-level American visitors are a common sight, including CIA Director John Ratcliff, Interior Secretary Doug Burgum and Energy Secretary Chris Wright. The Trump administration lifted sanctions on Rodríguez to confer further legitimacy and facilitate negotiations with US corporations. In Washington, the State Department continues to engage with Machado on rebuilding institutions and the economy.

According to Secretary of State Marco Rubio, the focus has shifted from ‘stabilisation’, as Venezuela has entered the recovery stage, from which the country will eventually hold free elections. ‘We have to be patient’, Rubio said, ‘but we also can’t be complacent.’ The multi-phase, cautionary regime management strategy results from legitimate concerns about a migration crisis and civil war. The hulking shadow of the Iraq War still inspires fear in American policymakers. Yet Venezuela does not presently appear bound for collapse and conflict, despite its precarious state and wily leader.

Instead, ‘Delcyping’ is underway. The portmanteau-cum-nickname for Rodríguez references Deng Xiaoping’s opening of the Chinese economy while keeping strict communist rule. Similarly, Rodríguez accedes to Washington’s commands for economic liberalisation while preserving her political control. Casting herself as the indispensable reformer, she will attempt to outlast the Trump administration by instituting rapid economic reforms paired with glacial democratic processes in hopes of negotiating with a future Democratic president unconcerned with Latin America.

Soon, then, the US must bring about credible democratic steps leading to elections, lest the Trump administration loses focus and accepts the status quo due to crises elsewhere. American control of Venezuelan oil revenues, combined with its deployment of sanctions, military assets and indictments, are more than enough to incentivise Rodríguez.

Given these gruelling circumstances, Venezuelans have demonstrated remarkable restraint. Their admirable patience, however, may prove fleeting should the iron fist of Chavismo maintain a tight grip on society. As popular discontent boils, Washington’s fears of disorder could become a reality.

If the Trump administration does not ensure a legitimate political reconciliation and the restoration of democracy, a pliant quasi-authoritarian Venezuela will only offer a temporary reprieve from the challenges confronting the Western Hemisphere.

In the meantime, Venezuela’s two competing visions for the future vie for American support. On 24 March, Machado told the S&P Global’s CERAWeek conference in Houston, Texas, that she endorses privatising the oil industry. Under the democratic opposition, she vows to bring free markets, property rights and the rule of law to Venezuela. The following day, Rodríguez participated virtually in the Future Investment Initiative summit in Miami to attract foreign capital and quash nervousness about corrupt institutions. Her feed cut out before the question-and-answer portion, an apt metaphor for how she governs.

Then there is the perennial Cuba problem.

Sixty-seven years of communist rule in Cuba may be headed for the ash heap of history following the loss of its South American patron. The oil-for-security-services deals had been a lifeline for the Cold War relic.

After cutting off Venezuelan oil to Havana in January, the Trump administration has used sanctions and tariffs—effectively enforcing an oil blockade—coupled with military threats and diplomacy to impose a maximum pressure campaign on the regime. As a result, Cuba endures a debilitating humanitarian crisis compounded by a collapsing, neglected energy grid and a crumbling, state-planned economy. The regime has undertaken negotiations with the Trump administration, striving to buy itself some time. 

As in the Venezuelan case, the Trump administration is seeking to apply economic and military coercion to produce multi-party democracy and market reforms without fomenting chaos. ‘You cannot fix their economy’, Rubio has stated, ‘if you don’t change their system of government.’

Yet the dynamics in Havana do not mirror those in Caracas. Trump is attempting to pressure an entrenched, cohesive communist regime to reform itself. Cuba is an ideologically committed one-party state without a pragmatic transitional figure desperate to avoid prison or a singular, unifying oppositional leader with legitimacy and capacity for organising. In short, Cuba has neither Rodríguez nor Machado.

President Miguel Díaz-Canel does not possess ultimate authority. The Castro family still holds significant power, namely Fidel’s elderly brother, Raúl Castro, who helms the ship of state from behind the scenes and directs talks with the US. His son, Alejandro Castro Espín, and grandson, Raúl Guillermo Rodríguez Castro, serve as intermediaries between Havana and Washington in the ongoing negotiations. His grandnephew, Óscar Pérez-Oliva Fraga, the deputy prime minister and minister of foreign trade and foreign investment, has also emerged as a potential agreeable alternative to Díaz-Canel, whom the Trump administration aims to remove. But any Cuban government headed by a Castro family member will be anathema to the powerful exile community in Florida, the domestic political ramification of which Trump must navigate.

Alongside Castro rule, the GAESA, Cuba’s military-run conglomerate, dominates its economy, presenting a thorny institutional barrier to engineering market reforms and reanimating key sectors.

Unlike Venezuela, moreover, pulling Cuba fully into America’s commercial orbit will require an act of Congress. A series of US laws govern US-Cuban normalisation, including the Helms-Burton Act, which stipulates that before Congress terminates the embargo, Cuba must hold free and fair elections, release all political prisoners, establish an independent judiciary and compensate exiles for confiscated property. In light of this legal architecture, the Castro regime’s decision to allow Cubans living abroad to invest in the island without substantive reforms to the communist system signals negligible overture rather than genuine capitulation.

Fans of the Cuban Revolution, of course, are in short supply. Disillusionment abounds on the island from endless rationing. Even the attention-seeking grandson of Fidel Castro, Sandro Castro, criticises Díaz-Canel and Cuba’s dismal situation. Still, the influencer progeny of revolution’s open call for more capitalism reflects the demands of average Cubans as much as his protected status. The Castro regime would tolerate widespread protests in favour of a free market economy about as favourably as erecting a steel sculpture of Adam Smith next to those of Che Guevara and Camilo Cienfuegos in the Plaza de la Revolución: Vas bien, Fidel, meets the invisible hand.

In the end, Trump may himself be forced to replace decapitate and delegate with dismantle and democratise.

If Havana bedevilled legions of US policymakers during the Cold War, Caracas assumed the mantle in the age of great power competition. Trump then decided the hemisphere could be reordered. His bid for an Americas First hemispheric order has delivered indicted fugitive leaders to justice and scored decisive tactical victories, but transforming operational successes into lasting political change requires sustained commitment, novel strategic thinking and adaptive execution. The US president has three years left to turn the region’s worst actor into ‘good neighbors’, amid a world in upheaval.