CUBA: A Very Long History of English Speakers’ Plots Against Havana

The United States’ troubled relationship with Cuba goes back much further than most think. As I explain in my book, The Occupation of Havana: War, Trade, and Slavery in the Atlantic World (UNC Press: 2018), the conflict started well before the Bay of Pigs invasion and the Cuban Missile Crisis or even Teddy Roosevelt and the Rough Riders’ infamous charge up San Juan Hill. Scroll back across the 19th century, but its origins lie further still, even earlier than the peak of U.S. annexationist interest in Cuba before the Civil War, when U.S. filibusterers plotted to invade and annex the island at the height of slave-state expansionism. 

The desire to control and possess the island of Cuba is ingrained in the DNA of the United States. It took hold in British North American minds before the origins of the nation. Beginning at least a century before the American Revolution, in the context of British imperialism in the Americas, British subjects and British North American colonials in particular wanted very badly to annex Cuba and were convinced that they would do so imminently. Very briefly in 1762, at the end of the Seven Years’ War, they did. That invasion and occupation is part of a centuries-long struggle that has been largely forgotten in the United States, even as we live with its tortured legacy in the present day.

Havana was founded 500 years ago on a marshy, inhospitable swamp, but a deep and welcoming bay, and the city has been an object of foreign interest since its earliest days. There is no time like the present — as Havana marks its 500th anniversary — to reflect on this past. As early as the 16th century, images, maps, and drawings of the island and its primary port began to circulate throughout northern Europe. Visitors’ accounts of Havana and the fantastical drawings they made of the city stoked Havana’s fame and foreigners’ desire to seize it. French pirates raided and burned the city to the ground in 1555, and English pirates like Sir Francis Drake attempted to do the same. When the Dutch pirate Piet Heyn captured the Spanish treasure fleet off the north coast of Cuba in 1628, he acquired so much wealth for the Dutch West India Company that it funded the Dutch army in its war against Spain for eight years and paid out a 400-percent dividend to shareholders that year. Dutch school children still sing a song that celebrates Heyn’s feat. 

Initially, the fascination with Havana derived not so much from the island of Cuba itself as the fabled wealth that flowed through its primary port. In the 16th and 17th centuries, Havana became known as a way station for the Spanish treasure fleets making the journey back to Spain with the gold and silver of Mexico and Peru, as well as silks, spices, and porcelain from Asia, traveling the transpacific Manila Galleon trade route and crossing Mexico by mule train. That wealth kept the Spanish monarchy afloat and funded its wars of territorial expansion in Europe in the century between 1550 and 1650. Tantalizing descriptions of the fleets — the amount of gold and silver they carried, their seasonal patterns, and the timing of their departure for Spain — inspired would-be raiders in northern Europe. Those convoys passing through Havana also allowed the city to grow, leading to royal investment and the rise of a vast service economy, which built creole fortunes and the city’s sprawling urban center. Growing prosperity added to the city’s allure and made it an even more desirable target of attack. 

In England, the obsession with capturing Havana and Cuba took particular hold. From the age of the Elizabethan sea dogs to the 1760s, British ships made a total of 12 attempts against Havana. Oliver Cromwell’s seizure of Jamaica from the Spanish in 1655 — an operation known as the Western Design — initially planned to target Cuba. The eventual conquest and retention of Jamaica, in the heart of the Gulf of Mexico, bolstered English confidence about its providential Protestant mission in its war against Papist Spain and landed them within sight of Cuba’s shores. During 18th-century imperial wars, Jamaica served as a launching pad for attacks against the Spanish Caribbean ports of Portobello, Cartagena, and Santiago de Cuba, but Havana remained the prize that got away.

From very early on, Cuba and its capital haunted the British and British colonial imaginary as a place that rightfully belonged in their hands. In English minds, the city’s acquisition was a virtual fait accompli. In 1671, an Englishman named Major Smith, who had been taken to Havana as a prisoner of war, reported in a letter that the Spanish “much dread an old Prophecy amongst them, viz. That within a short time the English will as freely walk the Streets of Havana, as the Spaniards now do.” In Smith’s alluring description of the city, there was already embedded a plan of attack. This battle plan and supposed prophesy foreshadowing and sanctioning it were reprinted multiple times over the ensuing century in sources as varied as a Philadelphia newspaper, a London book, and a sermon delivered in Boston. 

A fanciful rendition of Havana in a book engraving circa 1700. (Image from Wikipedia.)

The Black Legend of Spanish colonialism informed English animosity and provided motivation for these plots against Havana. The publication of Bartolomé de Las Casas’s Brief Account of the Destruction of the Indies — with its numerous print runs in London and Amsterdam — convinced English readers of the moral rectitude of their project and the ease with which it could be accomplished. An Anglo-American liberatory complex animated the minds of those who imagined taking over the city and acquiring territories in Spanish America. Despite their own use of enslaved Africans and dispossession of indigenous populations, English adventurers imagined themselves as avengers and liberators of Spanish America’s subjugated indigenous and African peoples, who, if given the opportunity, would rise up in arms and join them against their oppressors. When British forces successfully seized Havana in 1762, one English poet celebrated it as revenge for Cortés’s defeat of Moctezuma II at Tenochtitlán.

Embedded in this prophetic Protestant imaginary was an explicitly material interest in acquiring the city. Havana’s popularity as a target rested on a powerful economic logic to Britons in the mid-18th century, one that had been forged over centuries and that persuaded them that acquisition of the city would open access to vast amounts of Spanish silver. One of the fantasies of would-be attackers was unfettered entry to Havana’s lucrative market, where Africans could be exchanged for coveted Spanish silver. Havana was, they reasoned, the largest and richest city in the Caribbean, the stopping point of the treasure galleons, and it had an excellent, geostrategically situated harbor, “one of the finest in the World.” Like Jamaica, or Gibraltar in the Mediterranean (a frequent comparison), Havana’s harbor was seen as a crucial stepping-stone to trade, one that would offer control of the region’s sea-lanes and protect and bolster Britain’s commerce and slave trading with mainland Spanish America and its precious silvers and metals. 

The 13 North American colonies gained a reputation within the British Empire for the intensity of their Havana lust. In the 1740s, the Governor of Jamaica wrote to British war planners, “there is a vast spirit by all accounts in those of the Northern Colonies who in their imagination have swallowed up all Cuba.” Merchants in the northern colonies spoke of the boon it would be to acquire greater markets for the region’s products, while poor whites in the northern and mid-Atlantic colonies were tantalized by the prospect of gaining a plantation, a land grant, and/or enslaved Africans on the island of Cuba. A recruiting pamphlet in New York for a 1740 expedition to Guantánamo, Cuba, promised “an easy conquest” and that Spaniards would “fly before you and leave their houses, their negroes, their money, plate, jewels, and plantations, to be possessed by you and your posterity forever.” This dream was a product of the struggling colonists’ own social and economic ambitions, inspired by what they had heard or seen of the island or the West Indies in general, as well as the flow of English pamphlets, newspapers, and magazines that crossed the Atlantic. 

Havana’s famed Castillo de los Tres Reyes del Morro has defended the city since the 16th century. (Photo by Emmanuel Huybrechts.)

Not until the Seven Years’ War between Britain, Spain, and France (1754-1764) did the dream of conquering Havana finally come to fruition, and to do so, it took an extraordinary amphibious assault, drawing from all the resources of the British Empire and informed by the long succession of prior failed attempts. For this descent on Havana, British commanders mobilized more people than lived in any British North American city at the time, a force of 28,400 soldiers, sailors, and enslaved Africans from Britain, British North America, and the West Indies. Spanish soldiers and local militias from the island of Cuba, along with enslaved Africans who had been promised their freedom, fought off the attack for six suspenseful weeks, until British forces mined and blew up the fabled Morro fortress that stood at the entrance to Havana’s harbor. In total, more than 10,000 lives were lost, the majority to an outbreak of yellow fever that laid waste to the opposing armies. 

Despite its human and material costs, news of Havana’s surrender was met with joyous bonfires, fireworks, balls, and providential sermons in British territories throughout the Atlantic world. British drinkers toasted the great victory in commemorative glasses. In an address of thanksgiving delivered in New York, the Reverend Joseph Treat exclaimed, “What city, in all the Iberian dominions, is like unto this city, in riches and strength; And this is British property.” British and British American merchants were eager to capitalize on the tremendous windfall presented by their sovereign’s seizure of Havana. In the months after hostilities ceased, as many as 700 merchant ships sailed into Havana’s harbor from North America, the West Indies, Britain, and Africa to sell food, merchandise, and enslaved Africans to eager buyers in the occupied city. The British occupying governor surveyed Havana’s streets and gave them English names, which were affixed to the corners of intersections and on public squares. 

By the time invaders got their hands on Cuba, though, retaining it had become politically impossible — much as was the case during the 19th century, after U.S. seizure of Cuba in the Spanish–American–Cuban War. Havana, it turns out, was too important to lose. 

Theodore Roosevelt poses with other U.S. volunteers on San Juan Hill in 1898. (Photo by William Dinwiddie.)

Because all the decades of machinations had previewed British intentions, forces opposed to annexation had already positioned themselves successfully to obstruct it. Local resistance to British attack among residents of Cuba had been so fierce it incapacitated the British army, which could hardly hold the territory it claimed to have conquered. 

Charles III of Spain was so humiliated by Havana’s loss — contemporaries compared it to the defeat of Spain’s celebrated Armada — that he was willing to give up all of Florida for its return in the peace treaty negotiated at the end of the war. The policies that he adopted in the wake of Havana’s return extended unprecedented economic privileges to the island in order to bind it more tightly to the crown. Just a few decades later, Cuba was one of the largest sugar producers in the world, which heightened the rueful sense among English speakers that Havana was a city — and Cuba an island — that had slipped away. 

Britain’s imperial horizons shifted elsewhere, but its centuries-long obsession with possessing the island of Cuba became the political and cultural inheritance of the United States. In the cauldron of 19th-century politics, the memory of Havana’s capture and its regrettable return to Spain at the end of the Seven Years’ War haunted the nation to Cuba’s north. In altered form, it continues to do so to this day. What endured in the United States was a lingering sense of loss associated with the island, accompanied by the false belief that re-acquiring it would be easy. Five U.S. presidents tried to purchase the island, beginning with Thomas Jefferson’s first offer in 1808. If purchase was not possible, then perhaps another invasion would do. During the War of 1812, Andrew Jackson considered the option of invading Cuba. U.S. filibusters’ designs on the island during the 1840s and 1850s and the interest in Cuba of southern proslavery groups are relatively well known, but their roots go further back than most realize. They have their origins in British and British American slave trading and war making with Spanish America in the late 17th and early 18th centuries. 

Why this Havana lust? What did Cuba and its people do to deserve this fate? As the long historical view reveals, Cuba has had an outsized importance in world history, but at different times for different reasons. In the earliest colonial period, it was silver that gave the island geopolitical interest, in the 19th century, sugar, and in the 20th century, Cold War geopolitics. As Cuban diplomat and scholar Carlos Alzugaray Treto put it, the defining characteristics of Cuba’s relationship with the United States have been geographical — its proximity to the United States and asymmetry with it. In prehistoric eras, Cuba, the Bahamas, and the southeastern United States were all part of the same land mass. Residents of Cuba have struggled to avoid this destiny for centuries. The more fully we understand the longue durée reach of these Anglo-American machinations against Cuba, the more profoundly we can appreciate residents of the island’s centuries of resistance against the odds. This history is well known in Cuba and adds to the stubbornness of its government’s insistence that Cuban history is an ongoing struggle against Anglo-American plots. Much changes, but much remains the same.

Elena Schneider is Associate Professor in the Department of History at UC Berkeley. She spoke for CLAS on February 19, 2019.

(Select sections of this article are from The Occupation of Havana: War, Trade, and Slavery in the Atlantic World by Elena A. Schneider. Copyright © 2018 by the Omohundro Institute of Early American History and Culture. Used by permission of the University of North Carolina Press,

The northeast gate of the U.S. naval base at Guantanamo Bay, Cuba. (Photo by Bill Mesta/U.S. Navy.)

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