For over six decades, Cuba has been viewed as frozen in time: a closed, sclerotic regime with an economy in perpetual crisis and a people forced to innovate for survival. That image is outdated. The regime is fragile, its command economy exhausted, and amid the intensifying 2026 energy crisis—severe blackouts, fuel rationing, and economic paralysis triggered by halted Venezuelan oil shipments following U.S. actions—change could arrive abruptly.
The question, then, is not whether Cuba will transform, but whether the United States and its partners will be prepared.
Recent history provides clear precedents for the prospect of turbulent change. In November 1989, the Berlin Wall fell overnight, leading to the demise of the Warsaw pact. Two years later, the Soviet Union officially abolished itself. Countries that transitioned successfully benefited from pre-planned U.S. toolkits for market integration, including one standout innovation: Enterprise Funds—publicly capitalized, privately managed vehicles that delivered risk-tolerant capital to small and medium-sized enterprises (SMEs) in post-communist states like Albania, Ukraine, and Moldova when no one else would invest.
Cuba, like North Korea, is a relic of the cold war. But unlike North Korea, it does not have an outside patron in the form of China. Instead, it now faces a most uncertain future. If the regime should collapse, then Cuba would confront a comparable “starting from near-zero” scenario that took place in Eastern Europe after the fall of communism. Decades of central planning have hollowed out private-sector capacity: crumbling infrastructure (aging power plants, roads, ports, water systems), unreliable energy grids fueling nationwide blackouts, politically distorted productive sectors, and severe capital constraints. Traditional aid, technical assistance, or promises of future trade will not suffice to build a sustainable market economy. Early, catalytic investment is essential—capital willing to absorb political and regulatory risks while shaping a rules-based environment.
A Cuba Enterprise Fund should be designed now to target economically critical and politically stabilizing sectors:
- Energy: Modernize generation and transmission, invest in renewables, and reduce dependence on imported fuel to end blackouts and economic paralysis.
- Tourism: Shift from low-value mass offerings to higher-value cultural, ecological, and historical experiences, financing Cuban SMEs so growth benefits families rather than elites.
- Aviation, logistics, and infrastructure: Upgrade connections to regional hubs, modernize roads, ports, water, and sanitation to crowd in larger capital pools.
- Agriculture: Revitalize production to cut food imports, build resilience, and enable high-value exports integrated into global markets.
- Digital infrastructure: Support broadband and fintech for leapfrog opportunities with high returns from targeted capital.
These funds excel where grants fall short: providing patient, risk-tolerant capital to seed SMEs and local banking; modeling transparent governance and anti-corruption standards in crony-ridden settings; and operating with independent, professional management insulated from political interference. They blend public and private resources, demonstrate viable business models, de-risk early bets, attract diaspora capital through co-investment, and condition financing on reforms for transparency and enterprise freedom.
Timing is critical. Waiting until after regime change wastes the narrow window when political will and attention are highest. Begin planning now: define governance structures, outline sector priorities, assess capitalization ranges, and address legal/sanctions constraints. The fund can remain inactive until political and legal triggers are met, but starting the homework late risks missing the moment.
The Cuban diaspora could play a central role, contributing capital, managerial expertise, networks, and local knowledge. A structured fund amplifies their impact by enabling pooled, professional investments. International partners—Latin American democracies, European allies, and regional development banks—can rally around a U.S.-anchored fund for coordinated, non-fragmented support.
Cuba’s transition is a strategic imperative, not merely humanitarian. A stable, prosperous, market-oriented Cuba would reshape Caribbean and Latin American dynamics, reduce migration pressures, and diminish authoritarian influence.
The United States faces a choice: react ad hoc as events unfold, or prepare deliberately. The Trump Administration’s de facto blockade of Cuba appears to be imposing severe costs upon the Cuban regime. It would do well to plan now for a Cuba Enterprise Fund—a proven, practical instrument to help Cuba emerge as a freer, more stable, and prosperous neighbor. Creating a free and prosperous Cuba would not be a victory for Trump. It would be a triumph.
