Post-Castro, No Reform: Crafting a U.S. Strategy to Advance Cuban Freedom

El Capitolio Havana Cuba

When the United States loses sight of its foreign policy goals, decisions that affect millions of people often devolve into emblematic gestures and political theater. With regards to Cuba, the U.S. has always sought to stand with its people while opposing their authoritarian oppressors. For over six decades, different administrations’ approaches have swung like a pendulum, switching between inflexible isolation and abrupt engagement, to no end. This cycle has left the Cuban people behind. It’s time the U.S. acts on its unique leverage and reaffirms its commitment to a free and democratic Cuba. 

Raúl Castro stepping down as Cuba’s President in 2018 and First Secretary of the Communist Party in 2021 marked an end to the decades-long Castro era. Many hoped this vacuum might spark a wave of political and economic reform that would finally end totalitarian rule. Glimpses of hope came with the drafting of Cuba’s 2019 constitution that included reforms such as the recognition of private property and imposition of presidential term limits. 

It soon became clear, however, that the Castros’ handpicked successor, Miguel Díaz-Canel, would not bring an end to the Cuban people’s plight. The regime’s totalitarian grip has been emboldened via brutal crackdowns on dissent and free expression. Failed economic reform and the mishandling of the COVID-19 pandemic led to large-scale protests in July of 2021, which were met with the arbitrary detainment and horrific treatment of thousands of political prisoners, in addition to the harassment and persecution of journalists and activists. 

This isn’t anything new. Since Fidel Castro’s ascent in 1959, the Cuban government has ruled with an iron fist—imprisoning opponents, confiscating private property, suppressing free expression, and engaging in mass surveillance. In response to the seizure of American assets, alignment with the Soviet Union in the Cold War-era, and blatant human rights abuses, the United States imposed a trade embargo on Cuba beginning in 1960. The goal was clear: to pressure the regime to reform or, more optimistically, collapse. 

That was over six decades ago. 

The most serious criticisms of the embargo—outside of being a clear geopolitical failure—are its implications for human development. The embargo has isolated Cuba from the global market and stunted its economic growth. Yes, it ensured American capital hasn’t been used to embolden the Communist regime, but it undeniably left the economy stagnant and dragged the Cuban people down with it. 

Nowadays, and arguably more importantly of interest, the embargo has become political fuel for the Communist Party of Cuba (PCC): giving the regime an excuse for its own failures and oppressive behavior. Leaders use the embargo as a scapegoat for shortages and persistent poverty, all while rallying against it to boost nationalist fervor. 

The Trump Administration, spearheaded by Secretary of State Marco Rubio—the son of Cuban exiles—remains set on enforcing America’s hardline approach to Cuba. This strategy runs contrary to the pro-engagement efforts of the Biden and Obama eras. The U.S. has doubled down on sanctions on the Cuban regime and even reinstated Cuba’s designation as a state sponsor of terrorism. 

Taking a stand against the oppressive regime and standing with the country’s freedom fighters is admirable. The United States, leading with moral clarity, must take a stand to support a free Cuba. Simply lifting the embargo would send a message that would reward and reinforce the Cuban regime and similar authoritarian governments’ behavior; it’s nothing more than full-on capitulation. Furthermore, it would be a missed opportunity for the U.S. to give up the greatest piece of leverage it has over Cuba without guaranteeing any concessions. Yet, Cuba remains in desperate need of economic reform; blackouts plague the nation and the government, in the past few years, has even had to make pleas for American aid

It’s time for American policymakers to adopt a smarter, more dynamic strategy where leverage actually means change. The prospect of lifting the embargo and providing relief needs to be tied to guarantees of reform in Cuba. The 1996 Helms-Burton Act provides a framework for this proposal. It states that the embargo can only be lifted once Cuba legalizes all political activity, frees all political prisoners, ensures the protection of private property, and permits international observers to monitor elections and human rights protections, among other stipulations. 

To that end, the United States ought to approach both the Republic of Cuba and the international community with a proposal of conditional engagement. The agreement would combine an incremental easing of restrictions in exchange for steps toward democratization, market liberalization, and the institutionalization of the rule of law. Reforms must include: the release of all political prisoners; protections for free speech, a free press, an open civil society, and an unrestricted internet; the legalization of political parties that oppose the PCC; the scheduling of open elections under international scrutiny; guarantees of judicial independence; the implementation of anti-corruption measures within the government; and greater protections for private property. 

If Cuba meets these requirements, as verified by international observers from groups like the UN or Organization of American States (OAS), the U.S. would begin the easing of sanctions and restrictions: authorizing remittances, allowing tourism, diplomatic normalization, and permitting American economic activity with the Cuban private sector.

This approach ensures the pressure stays where it belongs: on the Cuban government. The embargo and its restrictions on Cuba’s access to the American market remain the U.S.’ greatest source of leverage over the island. Calls for an end to the embargo from Cuba and the UN can finally be answered. Any excuse for the PCC’s failures in governance would be gone. In offering a strategic bargain, Washington forces the Cuban regime’s hand. If they accept, it’s a victory for its people. If they refuse, the regime shows its populace and the world their true colors—it would rather maintain power than pursue progress, deepening dissent and internal pressure. 

So long as the Cuban regime embraces its people’s desires, the embargo will finally begin to be lifted. Power will return to the hands of the Cuban people. Polling data shows that Cubans overwhelmingly support greater private ownership, believe there is a necessary, growing dissent against the government, and hope to see regime change in the country. Rejecting appeasement and blind isolation while leveraging American influence ensures the U.S. actually stands with those it has claimed to defend for decades and offers a pathway to the future they demand. 

Ultimately, it’s time that purpose returns to prescribing the U.S.’ foreign policy. The Trump Administration has clearly laid out its posture of “promoting a stable, prosperous, and free Cuba” via a firm policy stance to hold the Cuban regime accountable. However, to truly advance that goal, symbolic toughness and blanket restrictions won’t be enough. America’s embargo on Cuba must no longer be the all-or-nothing litmus test of American politicians’ anti-Communist convictions. Rather, it should be tied to meaningful reforms that empower the Cuban people. 

The framework of America’s strategy towards Cuba should not be to simply punish the government for punishment’s sake. Rather, it’s time to create a transparent roadmap that provides hope to a distressed people while leaving their captors with little room to stall or spin. The pendulum must no longer swing. Via conditional engagement, the U.S. shifts its focus solely to the progress of Cuba’s people—creating a more stable and prosperous Latin America.

History supports this idea. In the late 1980s, under Mikhail Gorbachev, the Soviet Union undertook perestroika (a policy of economic liberalization), glasnost (increasing political freedoms such as speech and the press), and electoral reforms including the country’s first semi-competitive election. Together, these reforms allowed for an open civil society that enabled the discourse and dissent that brought about the collapse of the Soviet regime. It’s a very real possibility Cuba goes down the same path under this proposal.

The Cuban people demand change. It’s time to set the stage for a future of prosperity.

America has the opportunity to use its unique and strategic leverage to stand with the people of Cuba. A freer and more just society can be built in the Pearl of the Antilles… it might just take a little bit of outside-the-box diplomacy.

Featured/Headline Image Caption and Citation: Ukrainian Flag, Image sourced from Wikimedia Commons | CC License, no changes made

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