For months President Trump has focused intense pressure on Cuba — issuing threats, adding sanctions and ordering repeated intelligence flights off the island’s coast. Those moves, and the spike in surveillance sorties, have raised fears in Havana that Washington is preparing more than rhetoric.
Cuban authorities say they are prepared to talk about pragmatic matters — migration, drug trafficking and limited openings for Cuban‑American investment. But they insist that their sovereignty is not up for negotiation. As one U.S. reporter noted after interviewing President Miguel Díaz‑Canel, Cubans bristle at any suggestion that the United States can dictate who governs them or how they should run their country.
That sensitivity is rooted in a long history. U.S. interest in Cuba goes back long before the Cold War: it is woven into the expansionist logic of the Monroe Doctrine and the 19th‑century assumption that Cuba naturally belonged in the American orbit. Successive U.S. governments tried to buy, annex or otherwise dominate the island, often framing interference as a benign ‘‘civilizing’’ mission.
When Spain’s hold on Cuba collapsed in 1898, the United States did not allow full, unmediated independence. Washington occupied the island, installed military rule and judged Cubans — many of whom were formerly enslaved or of mixed race — unprepared for self‑government. Fears among U.S. elites of a successful Black republic in the Caribbean, after Haiti’s revolution, also shaped policy.
In 1902 Cuba was nominally made independent, but that independence came with strings. The Platt Amendment and related arrangements preserved broad U.S. rights to intervene in Cuban affairs and ensured heavy American economic and political influence. Over the following decades, U.S. businesses penetrated Cuba’s economy and a new education system, tourism and cultural exchange helped ‘‘Americanize’’ large parts of the island.
Everything changed with the Cuban Revolution. Fidel Castro’s early proclamation that the government would ‘‘Cubanize Cuba’’ was an explicit rejection of that long period of U.S. dominance. For decades many Cubans had internalized a deference to U.S. culture and power; the revolution set out to recover a distinct national identity and to defend sovereignty as a core principle.
To many in the United States, Castro’s program felt like an affront. Cuba had been treated in American imagination as part of the U.S. backyard — a playground for tourists and investors — so a revolutionary government asserting independence appeared threatening, even existential. That reaction shaped U.S. policy through the Cold War and beyond.
The revolutionary state framed its project around national independence, social justice and the ideas of José Martí, the 19th‑century Cuban national hero. For Cubans, the struggle was rooted in history and identity; for many Americans, it collided with a longer story about U.S. authority in the hemisphere.
Efforts at coercion have a long track record and mixed results. The Bay of Pigs invasion in 1961 is an enduring emblem of the risks of using force or covert action to try to change Cuba’s government. Periods of negotiation and rapprochement have also occurred: the Obama administration’s 2014 decision to restore diplomatic relations was hailed by some as a turning point, premised on the idea that engagement and respect for Cuban dignity and self‑determination would better serve both peoples.
The current U.S. posture — a return to pressure, punitive measures and muscular rhetoric — resonates with the older, neocolonial pattern of treating Cuba as something Washington can manage. That approach underestimates how deeply Cubans value sovereignty and how willing they have been historically to defend it.
If Washington’s goal is a safer, more cooperative relationship, history suggests coercion will backfire. A different path would begin by acknowledging Cuba’s right to determine its own leaders and policies, seeking common ground on practical issues, and building trust through consistent diplomacy rather than threats. The island’s past makes clear that any strategy premised on domination is not only morally fraught but also likely to fail.
