The Unlikely Biden-Trump Throughline on Cuba

On June 30, President Trump signed a presidential memorandum restoring hardline policies toward Cuba he first adopted in 2017 and that President Biden preserved throughout most of his term. 

Despite tough rhetoric, Trump’s memorandum is less a policy shift than a continuation, with a few possibly consequential tweaks.  

What stands out across Trump’s first term, Biden’s presidency, and Trump’s return is how consistent U.S. Cuba policy has remained. Trump I reversed the Obama-era détente, doubling down on the embargo while implementing some measures to foster the growth of the Cuban private sector. Biden left most of these policies intact, only pivoting away from them in his last days in office. Trump II is simply resuming policies that defined much of the last eight years.  

The biggest departure under Trump II is on Cuban immigration, not foreign policy. Biden legally admitted over 100,000 Cubans into the United States through the Cuba, Haiti, Nicaragua, Venezuela (CHNV) humanitarian parole program to manage the border crisis. Trump ended that program in April, pushing the newly resettled Cubans into undocumented status and urging them to self-deport—a move that has alienated many Cuban-American Trump supporters in Florida and some Republican lawmakers. The June 30 memo seems aimed at placating them by creating the appearance, at least, of a tough new approach to the communist regime. Political scientist Javier Corrales described it as “ideological signaling”—symbolic but low cost. 

In fact, the new memo largely mirrors Trump’s 2017 version, with updated language on immigration to match current priorities. It avoids drastic new restrictions on flights or remittances and does not target informal cash couriers or food delivery apps, which remain vital lifelines for Cubans facing shortages. So far, this is not a radical new form of maximum pressure, even if the administration might like to present it that way.  

Where it does have the potential to break ground is in confronting the Cuban military’s economic dominance—a goal Biden shared. Cuba’s armed forces control Grupo de Administración Empresarial S.A. (GAESA), a vast business conglomerate spanning sectors as varied as tourism, agriculture, and industry. This structure has ensured the Cuban military—and by extension, intelligence and security personnel—capture most incoming foreign investment and hard currency, making them the dominant faction within the regime.  

Other civilians and military figures in the communist party, though opposed to political liberalization, see market-oriented reforms as the only path to regime survival. Post-COVID, the Cuban state has struggled to keep its power grid running, revive a shrunken tourism sector, pay back foreign loans, or stem mass emigration and rising violent crime. Countries like China and Vietnam—authoritarian regimes that embraced market economies—are urging Cuba to follow suit, not out of altruism but out of frustration at unpaid loans.  

Oddly enough, both the United States and its adversaries share an interest in nudging Cuba toward a more open economy—albeit for different reasons. 

Currently, GAESA and the military figures who profit from it remain stronger than the island’s nascent private sector, which employs only about a third of the labor force. Biden and Trump I tried to nurture private enterprise, but reforms have been halting, and late last year Havana imposed several new restrictions on private sector activity.  

Trump’s new memo introduces a possible innovation: secondary sanctions on foreign firms doing business with GAESA or Cuban military-linked individuals—many of them Spanish, Canadian, and Australian companies. Unlike the 2017 memo, this one explicitly bans “direct or indirect financial transactions” with these entities. A separate executive order would be needed to implement these sanctions—but the possibility alone may shrink the military’s pool of foreign business partners.  

Ricardo Herrero of the Cuba Study Group explains that “Meliá (a Spanish tourism company that owns over 30 hotels in Cuba and has dealings with GAESA) won’t immediately pull out, nor will Sherrit (a Canadian company in nickel and cobalt mining). But there will be a chilling effect on any new foreign firms looking to do business with GAESA or the Cuban military.” For two years, Herrero says, Spanish firms have sought to reduce their direct dealings with Cuban state enterprises, looking instead to partner with private sector companies. The Trump administration, by leveraging the threat of secondary sanctions, may prompt more third country firms to follow suit.  

Ultimately, the clash between reformers and the military will likely hinge on ex-president Raúl Castro, still politically influential at 94. After he passes away, tensions between regime factions may erupt. The United States has a stake in ensuring that if such a split occurs, pro-market elements—rather than those favoring continued state control—prevail. 

Secondary sanctions carry risks. They may deepen Cuba’s economic crisis, worsening conditions for ordinary people and driving further migration. Although many Cubans are now choosing countries like Brazil or Uruguay, a sharp downturn could prompt renewed irregular migration to the United States. 

There’s also the risk of inadvertently ceding more ground to China. If U.S. pressure drives out Western investors, Beijing could step in—especially in mining and energy. China is already building Cuba’s solar infrastructure and could use increased leverage to expand intelligence-gathering capabilities on the island.  

Even if the United States succeeds in weakening the Cuban military’s economic dominance, political liberalization is unlikely. Cuba’s security services still hold the monopoly on violence. As Corrales puts it, the “the security apparatus is not weak or unwilling (to repress),” as seen in its response to the mass demonstrations of July 2021, March 2024, and June 2025. 

Among Trump’s recent moves in Latin America—from targeting Mexican cartels to pressuring Panama over Chinese influence—his Cuba policy is the least surprising. The regime remains stable, if brittle, and major transformation remains a long shot. The continuity between Biden and Trump on Cuba reflects a shared understanding: Cuba policy signals intent but rarely changes outcomes. Secondary sanctions—the only truly new element of Trump II Cuba policy, to date—might tweak the balance of power on the island, but they are unlikely to transform it.