Ronald Reagan Institute
U.S. Policy That Favors Freedom in Venezuela and Cuba
By Jamie Fly

The Trump Administration has prioritized the Western Hemisphere in a way that no other administration has since Reagan. Inheriting an open border from President Biden, President Trump rightly realized that Americans’ security and prosperity are inextricably linked to the security and economic well-being of the almost 500 million inhabitants outside North America in our own hemisphere. His administration has appointed senior officials with deep understanding of the region who have diligently pursued regional engagement and partnerships.
Thus far, beyond summits and visits, the administration’s engagement in the region has prioritized military pressure and economic partnership. This Trump Administration bias toward economic statecraft addresses a longstanding gap in U.S. geopolitical strategy. America was far too slow to engage its partners economically while China, Russia, and other actors offered a broad set of inducements. President Trump is personally agnostic toward regime type, so long as the regimes in question are compliant with U.S. demands.
Yet a value-free approach to international relations has its costs. While deals may be closed in the short term, investments will be at risk in the long run without sustainable progress on rule of law. U.S. companies operate on a risk assessment timeframe of decades, not months. Many major players in key sectors like finance and energy have been badly burned by past engagements in unstable markets in the region.1 Only by supporting true democratic change will the Trump Administration ensure its regional gains endure.
The administration’s geopolitical maneuvering presents two clear opportunities for true democratic reform of staunch authoritarian regimes. Progress in Venezuela and Cuba could fundamentally reshape the fate of the region and America’s position in it. The geopolitical positioning of Venezuela—with the largest proven oil reserves in the world—has global implications. The Castro regime in Cuba has provided a perch 90 miles off U.S. shores for America’s adversaries for decades. Conversion of both to functioning democracies would be a significant blow to the attempts of America’s authoritarian adversaries to leverage allies in our own hemisphere.
The Trump Administration is attempting to manage these potential transitions without utilizing the significant programs that were established by Congress during the Cold War that led to the collapse of Soviet communism. U.S. democracy assistance programs have been largely eliminated by the restructuring at the onset of the second Trump Administration. U.S. civilian broadcasting has also been thrown into chaos, underutilized to reach audiences in the Western Hemisphere or globally. The Trump Administration has yet to elaborate its vision for democracy assistance to replace frozen programs.
The administration eviscerated democracy assistance programs in part because some in the administration viewed them as not delivering results. Others, affiliated with the isolationist camp within MAGA, felt that the United States should not pursue democratization as a goal. While many important programs were needlessly discarded, there is some reason to reassess decades of efforts that have only resulted in 20 years of global democratic decline, according to Freedom House.2
Over the last 25 years, U.S. democracy assistance programs often tried to do too much. U.S. programs were often constructed with broad and unattainable goals. The State Department and USAID struggled to prioritize and missed key moments where significant intervention in a smaller subset of countries might have turned the tide in favor of freedom. Systemically, these programs often failed to connect U.S. economic statecraft to democracy. They tended to create superficial ecosystems of NGOs and democracy activists increasingly disconnected from the citizens of their countries that had no lasting business model other than more international assistance.
With the authoritarians under pressure and the best opportunities for democratic change in decades, Congress and the administration should work together to define a new set of democracy tools that are relevant for the 21st century, adapting lessons of the past for the present.
U.S. programs should still fund independent journalists, political activists, lawyers, religious freedom advocates, and other changemakers in their societies. They should be short-term programs that assume that the individuals in question will drive impact, not establish a structure to enrich themselves for decades on end. They should seek integration with economic changemakers in society who can drive real benefits for the population, which is essential to lasting progress on the path to democracy. U.S. democracy programs should be better coordinated and linked to U.S. trade promotion and economic assistance programs including the Millennium Challenge Corporation, the U.S. International Development Finance Corporation, and related entities.
Once authoritarian control over a country is challenged, a viable path toward democracy needs to be supported. Elections will need to be organized and held. The United States cannot bring about the conditions for free and fair elections and then back away and provide no support to the forces of freedom contesting those elections. On the other side, Russia, China, and Iran will be arrayed with resources and technical assistance. U.S. programs should learn from the authoritarians’ tactics and ensure that our allies have the means to fight back.
These tools can be deployed in Venezuela and Cuba in the coming months. Given U.S. leverage and the ties between our countries, freedom-focused policies do not have the same level of risk as U.S. forays in Iraq and Afghanistan. As Secretary of State Marco Rubio has said, “This is not the Middle East. And our mission here is very different. This is the Western Hemisphere.”3
Venezuela is the most fertile ground for a new approach. The masterful special forces raid that captured Nicolás Maduro has created the possibility of real change in one of the region’s largest countries. It has also deprived Russia, China, and Iran of a key regional partner and decimated Cuba’s economic stability. Finally, it has created opportunity for U.S. companies who were previously driven out by Maduro.
Yet the removal of Maduro has had limited impact on the well-being of the Venezuelan people. Political prisoner releases have been limited and the proceeds from oil sales—which the Trump Administration indicated would be put into escrow to benefit the Venezuelan people—have not led to tangible economic reforms. In recent weeks, Venezuelans have taken to the streets to protest the lack of economic progress and opposition leaders predict that more protests are likely.4
Economic stabilization in Venezuela will not be possible so long as remnants of the Maduro regime run the country. The administration should push toward early elections. Opposition leader María Corina Machado should be supported in her efforts to return to make her case directly to the Venezuelan people. U.S. leverage over interim ruler Delcy Rodriguez should be used to dismantle the regime’s repressive apparatus, including the full and unconditional release of political prisoners. The administration should also work through the embassy in Caracas to ensure that Venezuela’s economic success strengthens the living conditions and economic wellbeing of Venezuelans. The administration says that this is happening, but there is very little transparency about the details.5
The capture of Maduro and the pressure exerted on the Venezuelan regime has created an opening for democratic change in Cuba. The Trump Administration’s removal of Maduro has deprived the regime in Havana of a key economic lifeline and strategic partner. The regime’s ability to manage its economy has been faltering, and targeted administration pressure has brought the regime to the brink. Most provinces in Cuba now only have several hours of power a day, bringing much of the Cuban economy grinding to a halt.
Given the restrictions imposed in U.S. law by the 1996 Helms-Burton Act, the Trump Administration will have difficulty relying on regime elements in Havana as it has in Caracas. A successful Cuba policy should support the Cuban people and independent civil society while limiting resources, legitimacy, and geopolitical advantage of the regime. U.S. democracy assistance programs should be relaunched to help shape conditions that expand civic space, strengthen independent actors, and constrain repression. The administration should maintain pressure on the regime to release political prisoners and dissolve the security services that have targeted the Cuban people and undermined U.S. national security.
Gains in Venezuela and Cuba are not guaranteed. The remnants of the authoritarian regimes in power will do everything possible to ensure their long-term survival. America’s adversaries—from Moscow to Beijing—will be seeking to reestablish a presence in America’s neighborhood. True hemispheric stability will only be possible if the region becomes freer. Freedom does not just allow citizens to flourish; it creates a sustainable environment for investment and trade and makes conflict less likely. It also disincentivizes migration to the United States.
The openings in the Western Hemisphere present a generational opportunity to reform U.S. democracy assistance tools and put them into practice in our own neighborhood. It is an opportunity that should not be wasted.
[1] Spencer Kimball, “Exxon CEO Says Venezuela Needs to Transition to Democracy for Oil Investment to Make Sense,” CNBC, January 30, 2026, https://www.cnbc.com/2026/01/30/exxon-ceo-says-venezuela-needs-to-transition-to-democracy-for-oil-investment.html.
[2] Yana Gorokhovskaia, Cathryn Grothe, and Amy Slipowitz, “Freedom in the World 2026: The Growing Shadow of Autocracy,” Freedom House, March 19, 2026, https://freedomhouse.org/report/freedom-world/2026/growing-shadow-autocracy.
[3] Tara Suter, “Rubio on Venezuela Action: 'This is Not the Middle East,'” The Hill, January 4, 2026, https://thehill.com/policy/defense/5671811-rubio-venezuela-not-middle-east/.
[4] Steve Hendrix, “Trump Says Venezuela's Economy has People 'Dancing in the Streets.' Not Quite,” Washington Post, June 3, 2026, https://www.washingtonpost.com/world/2026/06/03/trump-says-venezuelas-economy-has-people-dancing-streets-not-quite/.
[5] Roxanna Vigil, “The U.S. Took Over Venezuela's Oil Industry. Where Has All the Money Gone?,” Council on Foreign Relations, June 3, 2026, https://www.cfr.org/articles/the-u-s-took-over-venezuelas-oil-industry-where-has-all-the-money-gone.
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