Cuba Before The Fall

 By: Raymond A. Pérez

National Capitol Building, Havana, Cuba

The boats are still – but that can change at the drop of a regime.

Washington has managed Cuba through the same framework for sixty years. The results are documented and unremarkable. But before we proceed, let’s be clear – the Cuban government failed its people. If we are looking to assign blame, we have enough evidence. Sixty-seven years is sufficient evidence.

The embargo, a strategy that came in response to what emerged in Cuba, did not quickly remove the Castro government. It did not liberalize the economy, nor did it orchestrate the swift democratic transition it was designed to accelerate. What it did produce was the economic desperation that drives emigration, and a political dynamic in which the regime blamed every failure on the United States rather than on itself. But now, let’s get beyond the blame game and focus on the current landscape and the path to future prosperity.

Cuba sits ninety miles from the United States with a population of eleven million people, an economy in structural collapse, and a government that has run out of both options and credibility. Fuel shortages have paralyzed transportation. Blackouts last twelve hours or more. Food distribution has deteriorated to levels not seen since the Special Period of the 1990s, when the Soviet subsidy disappeared overnight and Cuba lost a third of its GDP in four years. That crisis produced one of the largest refugee flows in the history of the Florida Straits. The conditions today are worse, the external lifeline thinner, and the political legitimacy of the regime more exhausted than it has ever been.

The migration arithmetic is not complicated. When economies collapse without a credible path to stabilization, people leave. They leave by any means available. The Florida Straits have absorbed that pressure before, during the Mariel boatlift of 1980 and the rafter crisis of 1994, each of which required emergency federal response and produced lasting political consequences. Neither of those crises occurred against the backdrop of the current level of economic disintegration. The regime today cannot provide power, food, or a story about the future that anyone believes in. The population knows it. The emigration data reflects it: Cuban migration into the United States reached record levels in fiscal years 2022 and 2023, surpassing even the historic peaks of prior crisis periods. Since 2020, Cuba’s population has declined by nearly 1.4 million people. This type of demographic contraction is of a magnitude typically associated with armed conflict, not peacetime economic failure.

The question is not whether Cuba’s crisis will produce a migration event. It is whether the United States engages now on its own terms and with structural conditions attached, or responds later, reactively, at the border. What should these conditions contain? These answers require a much larger print than can be captured here. But these answers will serve as the platform for democracy and economic stability in Cuba. 

An engagement framework is not an ideological concession. It is a practical instrument. The Cuban economy has identifiable sectors, including tourism, critical infrastructure, agriculture, energy, and telecommunications. Targeted foreign investment in these areas, structured through transparent mechanisms with independent oversight, could generate the stabilization that prevents displacement. The same logic that applies to Venezuela’s resource sectors applies here: capital without accountability does not stabilize economies. It captures them. Any framework for Cuban engagement must include clear investment parameters, verifiable revenue transparency, and a fiduciary oversight structure that ensures proceeds reach the general population rather than regime-linked intermediaries. The architecture for that structure exists. What is missing is the political will to require it as a condition of engagement rather than an aspiration attached to it.

The harder conversation is the one that follows regime removal, and it needs to happen now, before that moment arrives rather than after it. History is unambiguous on this point: countries that avoided post-authoritarian migration crises were the ones that entered the transition with an economic plan already in place. The ones that did not produced displacement. A post-regime Cuba without a credible stabilization framework, without a path to property rights, banking normalization, small business formation, and reintegration of the diaspora’s capital, will not retain its population regardless of the political outcome. People do not stay because a government fell. They stay because there is a reason to remain. That means a transition plan that addresses employment, currency stabilization, land and property rights, and the reestablishment of rule of law as economic preconditions, not political afterthoughts. The diaspora, concentrated in South Florida and representing decades of accumulated capital, professional expertise, and institutional knowledge, can be the most significant asset in any Cuban transition scenario. A serious framework activates that resource. An improvised one watches it observe from a distance.

The sovereignty objection will arrive on schedule and should be answered the same way it should be answered in Caracas: a government’s right to exclude accountability is not sovereignty. It is impunity. Cuba’s people have not exercised meaningful economic agency in over six decades. A structured engagement framework does not take sovereignty away from Cubans. It creates the conditions under which they can eventually exercise it for themselves.

The United States has legitimate security, political, and economic interests in Cuban stability. South Florida has a direct and measurable stake in what happens when those conditions deteriorate. The choice is not between engagement and principle. It is between a managed, structured approach to Cuban economic stabilization now, or an unmanaged humanitarian crisis at the doorstep later. Over sixty years of the same policy has produced a Cuba that is more desperate, more isolated, and more dangerous to regional stability than it was when that policy began.

The boats are still. But they won’t be indefinitely. The time to build a framework is before the fall, not after it.

Raymond A. Pérez is the Founder and Senior Managing Director of Miami-based Frontera Capital Advisors, LLC, specializing in cross-border mergers & acquisitions (M&A), restructuring, and fiduciary oversight. With nearly four decades of experience, he has advised public and private sector clients on complex transactions throughout Latin America and the Caribbean. He previously led the regional corporate finance practices for both a Big Four and a publicly traded global consulting firm.