Donald Trump is the 13th consecutive US president to seek a political trophy in Cuba. He recently signalled that his goal is within reach, stating, “I do believe I will be having the honour of taking Cuba.” But as the island teeters on economic collapse, experiencing its greatest mass exodus and a profound lack of confidence in the regime, the "win" being chased in Washington looks nothing like the democracy Cubans have spent generations fighting for.
Cuba is currently descending into periodic darkness. Dwindling oil reserves, exacerbated by a de facto US oil blockade following the capture of Nicolás Maduro in Venezuela, have forced the Castro family to the bargaining table. Yet, despite the regime's desperate position, the White House has largely sidelined meaningful political change. Reports suggest a strategy that hinges on the regime remaining intact. The administration is reportedly seeking the removal of President Miguel Díaz-Canel — an unpopular figurehead — as a primary condition for economic progress.
This is not a substantive political opening. It is a tactical reshuffling that would allow the Castro family and the Cuban military to consolidate power in exchange for compliance. Such a deal would crush the aspirations of Cubans at home and in exile who seek the democratic rights that were the supposed raison d'être of the 1959 revolution.
Democracy has long been elusive for Cuba. For two centuries, the island has been subordinated to foreign interests — enduring Spanish colonialism, US occupation, and a Soviet-propped regime. Yet, this history of subordination has never extinguished the fire of resistance. My own family history reflects this: my great-grandfather fought Spanish rule in the 1890s; my grandfather worked to topple the dictator Gerardo Machado in the 1930s; and my parents, seduced by Fidel Castro’s promises of constitutional restoration, hid guns for the revolution.
Fidel Castro famously failed to deliver. Instead, he militarised society and used firing squads to eliminate dissent. Thousands, including my parents, fled. Our exile was meant to be temporary, a brief wait until the United States toppled the regime. That day never came. Instead, the military expanded its grip, eventually controlling tourism, retail, and foreign investment.
The government has always been creative when desperate for cash. In the 1970s, as Soviet subsidies dried up, Havana turned to the very people it labelled "worms" — the exiles. I participated in those dialogues, which led to the release of 3,600 political prisoners. While imperfect, those negotiations offered a glimpse of a real opening.
What is on offer today is far more cynical. Cuban officials are not being asked for genuine concessions. Superficial gestures, such as allowing limited diaspora investment or releasing a handful of prisoners, are being mistaken for compromise. If negotiations continue on this trajectory, the resulting government will be the same one that, in 2021, brutalised thousands of protesters for demanding freedom of speech. This is not a regime that should be empowered by U.S. policy.
The White House should condition any investment on verifiable reforms, most importantly, the removal of the military from economic management. President Trump must negotiate safeguards ensuring that US dollars do not flow directly into military coffers. A regime should not receive an economic lifeline while political prisoners languish in cells or speech remains restricted.
Cuba’s leadership is weak and desperate. President Trump does not need to trade away the island’s political future for the brief, symbolic triumph of a signed deal. Negotiations must be rooted in the democratisation and demilitarisation of the island, not just economic pragmatism.
To accept anything less is a betrayal. It signals to Cuban Americans that their political voice is incidental and tells the residents of the island that their freedom is a tradable commodity. Cubans everywhere have fought too long and sacrificed too much to be handed a deal that merely replaces one form of authoritarianism with a more compliant version of the same. We deserve a future defined by our own voices, not a bargain struck in the shadows of foreign interests.
The New York Times