The United States has a long, tortured relationship with Cuba, including Thomas Jefferson’s imperial designs on the island. As Clay travels to Cuba this week to lead a cultural tour, he reflects on a bit of forgotten history between the U.S. and the island nation 90 miles from Key West, Florida.
Thomas Jefferson long harbored a desire to make Cuba part of the newly forming United States. In 1809, he wrote to James Madison outlining his dream to erect a column on the Southernmost limit of Cuba inscribed: “Ne plus ultra [i.e., thus far and no farther].”
“I candidly confess that I have ever looked on Cuba as the most interesting addition which could ever be made to our system of states.”
Thomas Jefferson to James Monroe, 1823
The Republic of Cuba is just 90 miles from Miami. The 777 mile long island is the jewel of the Caribbean, located at the mouth of the Gulf of Mexico (now also called the Gulf of America), poised equally between Mexico’s Yucatan Peninsula and the state of Florida. As the United States gobbled up the northern hemisphere in the 19th century — the Louisiana Purchase (1803); the Floridas (1819); Texas (1845); Upper Mexico (the American Southwest, 1848, 1854); the Oregon Country (1846); Alaska (1867); and Hawaii (1898); not to mention Puerto Rico, Guam, the Marianna Islands, American Samoa, and the U.S. Virgin Islands — it’s hard to understand why we didn’t grab Cuba while we were at it, especially after the U.S., most colorfully represented by Theodore Roosevelt and his Rough Riders, “liberated” Cuba from Spanish domination in 1898.
I’ve never understood this omission of empire. Incorporating Cuba into the United States makes more geopolitical sense than Hawaii or Alaska. At the heart of the Caribbean, in the soft underbelly of the United States, lies a huge and exceedingly fertile island, the 17th largest in the world (about equal in size to Iceland and Newfoundland), with an outstanding harbor (Havana). If the goal is “fortress America” and the enforcement of the Monroe Doctrine (1823), you’d want Cuba. You certainly would not want Cuba to be under the control of a hostile power, which explains America’s Cold War relations with Cuba and the USSR.
The U.S. occupied Cuba between 1898 and 1903 and still occupies Guantanamo Bay (45 square miles) on the southeast coast of the island. The U.S. has been “leasing” Guantanamo since 1903 over the continual stiff protests of the Cuban government. Several presidents have vowed to close the American naval base at Guantanamo. None has succeeded.
The United States has made purchase overtures to Cuba at least four times, twice formally. In 1848 President James K. Polk (the great expansionist) offered Spain $100 million ($4 billion in today’s currency) for Cuba. Spain declined. In 1854, President Franklin Pierce offered $120 million ($5 billion today). Spain declined.
When the U.S. could have simply annexed Cuba in 1898, it chose not to do so. In the Congressional bill authorizing war against Spain in April 1898, Senator Henry M. Teller of Colorado introduced an amendment declaring that the United States “hereby disclaims any disposition of intention to exercise sovereignty, jurisdiction, or control over said island except for pacification thereof, and asserts its determination, when that is accomplished, to leave the government and control of the island to its people.” Amazing. Teller’s logic was not entirely altruistic, however. In addition to being squeamish about America taking on an offshore imperial agenda, Teller wanted to protect the American beet sugar industry from cheap Cuban cane sugar imports.
As America’s occupation ended in 1903, Congress passed the Platt Amendment, named for Connecticut Senator Orville Platt, laying out post-war relations between Cuba and the United States. Among other provisions, the amendment declared that “the United States may exercise the right to intervene for the preservation of Cuban independence, the maintenance of a government adequate for the protection of life, property, and individual liberty.” The U.S. exercised that right in 1906–09, 1912, and 1917–22; and came close to invading the island in 1962 during the Cuban Missile Crisis.
The United States may have declined to annex Cuba outright, but we have occupied it off and on, threatened it repeatedly with military intervention, transformed it into an American economic colony, refused to return Guantanamo, encouraged “freedom fighters” to overthrow Castro’s revolutionary government, and generally kept our big Yankee boot on the neck of the Cuban people since 1960. Thanks to unrelenting American hostility, Cuba has never had the opportunity to establish itself as an economically viable sovereign nation. It is true, of course, that Fidel Castro, after the success of the 1959 revolution, at times consolidated his control of the island by way of summary executions, torture, disappearances, violations of civil rights, censorship, and a refusal to hold open elections. He is gone now, and his brother Raul is weak and elderly, so the future of Cuba is unclear.
Although President Donald Trump has declared his interest in making Canada the 51st state, annexing Greenland, re-grabbing the Panama Canal, and renaming the Gulf of Mexico to Gulf of America, so far he has not expressed a desire to pocket Cuba.
America’s on-again, off-again desire to absorb Cuba goes all the way back to the Founding Fathers, including, ironically, America’s apostle of freedom and self-determination, Thomas Jefferson.
Jefferson, the Imperialist
Clay’s sketch of Thomas Jefferson’s “modest vision” that both Canada and Cuba would be part of a great U.S. “Empire for Liberty.”
Thomas Jefferson is a man of paradox — the liberty-loving slave owner, the man of public frugality and private bankruptcy, an admirer but also a dispossessor of Native Americans, a strict constructionist who purchased the Louisiana Territory, a man who said he abhorred race mixing and did some himself.
Jefferson’s purest vision was for a mild-mannered republic of subsistence-plus family farmers, diffused evenly across the landscape, working moderately hard in the fields and gardens by day and reading Homer in the original Greek at night. It was an agrarian utopian dream born from the pages of Horace and Virgil, untethered to economic or political reality. That was one Jefferson. The other Jefferson was an unapologetic imperialist who wanted North America (and a bit beyond) to be an exclusive American homeland. A tabula rasa on which to write “the pursuit of happiness.”
The purchase of the Louisiana Territory in 1803 doubled the United States for 3 cents per acre, extending the western border of the U.S. from the Mississippi River to the crest of the Rocky Mountains. President Jefferson wasn’t seeking all that territory in 1802-03, but when Napoleon suddenly offered those 575 million acres to the U.S. for $15.6 million dollars, Jefferson exulted despite his quiet qualms about the constitutionality of the purchase.
Jefferson also wanted Canada — found it frustrating to think that Great Britain continued to control part of the North American continent — and supported American invasions of eastern Canada first during the Revolution and then during the War of 1812. He also wanted Cuba off and on and sent emissaries to Havana in 1808 during his second term to inquire (with Spanish colonial officials) about the island’s purchase.
The Paradox
Jefferson’s imperialism and his utopian vision of an American agrarian republic are incompatible. Like the rest of the Founding Fathers, Jefferson was influenced by the French political theorist Montesquieu’s 1743 treatise, The Spirit of the Laws. Montesquieu assured political thinkers that a republic is a very special form of polity that can only work on a small patch of land — a city-state like ancient Athens or Renaissance Florence. In the U.S. this would suggest that Rhode Island might be a republic, but not Texas. Jefferson knew this — somewhere deep in his thinking — but he and his lieutenant James Madison racked their brains and strained their political consciences to make the case that it really doesn’t matter how large your republic is, so long as you divide and subdivide it into more manageable units. At one point Jefferson spoke of “the republic of the farm.”
There is no soothing way to say it. The “small-r” republican Thomas Jefferson dreamed of empire. At the very least, he wanted everything between the Atlantic and the Pacific, from “sea to shining sea,” as the late Stephen Ambrose liked to put it. He let himself believe that an empire is not necessarily bad so long as you make it “an empire for liberty.” He thought about this endlessly — knowing full well that he was probably kissing his classical agrarian republic goodbye. He concocted ingenious schemes to give republicanism a chance on so large a canvas: small, square, identical states west of the Appalachian Mountains; publicly sponsored agricultural colleges and learned societies; a foreshadow of Lincoln’s Homestead Act to get land into the hands of the have nots; and emphatic public education. Jefferson wrote to Charles Yancy in 1816, “If a nation expects to be ignorant & free, in a state of civilisation, it expects what never was & never will be.”
Jefferson wanted his “empire for liberty” so fervently that he was willing to be ruthless in order to achieve it, particularly concerning Native Americans, whom he admired deeply so long as they didn’t stand in the way of America’s westward expansion. To secure his empire, Jefferson set in motion the dispossession of the Native Americans east of the Mississippi and — sooner or later — beyond. He urged his compatriot William Henry Harrison, the governor of the Illinois Territory, to grant lots of easy credit to Native American leaders and — when they couldn’t pay their bills with furs — to convince them to cede their homelands to the United States instead. For Jefferson, American Indians had only three choices: 1) cede their lands to the United States and move west beyond the Mississippi River (i.e., voluntary removal); 2) give up their resistance and assimilate rapidly and nearly fully into the Anglo-American world; or 3) continue resistance and face wars of extermination.
Jefferson’s land lust was almost immeasurable. On April 22, 1809, he wrote an astonishing letter to his closest friend and collaborator, James Madison. In it, he wrote that he wanted Canada and also hoped Napoleon would facilitate America’s annexation of Cuba, but he assured Madison that then he’d be content — with an American republic that extended from the Atlantic to the Pacific and from the North Pole to the bottommost tip of Cuba: “I would immediately erect a column on the Southernmost limit of Cuba & inscribe on it a Ne plus ultra [i.e., thus far and no farther] as to us in that direction. We should then have only to include the North [i.e., Canada] in our confederacy, which would be of course in the first war, and we should have such an empire for liberty as she has never surveyed since the creation: & I am persuaded no constitution was ever before so well calculated as ours for extensive empire & self government.”
When Frederick Jackson Turner came to write his famous essay, The Significance of the Frontier in American History, in 1893, he made it clear that America’s flirtation with a true republic ended with Jefferson’s Louisiana Purchase, just 15 years after the ratification of the Constitution. Holding together and governing that much territory (the size of Europe) would require a much stronger, more centralized government than Jefferson envisioned at his aerie on the mountaintop.
In a post-presidential letter to his protégé James Monroe in 1823, Jefferson wrote, “I candidly confess that I have ever looked on Cuba as the most interesting addition which could ever be made to our system of states.” But rather than invade the island, Jefferson said he was content to “lie still, in readiness to receive that interesting incorporation when solicited by herself [i.e., Cuba].” Jefferson always assumed that America’s problems (like slavery) would be solved magically, without violence or chaos. That moment never came.
Jefferson said the annexation of Cuba “is exactly what is wanting to round our power as a nation, to the point of it’s utmost interest.” To acquire Cuba would “fill up the measure of our political well-being.”
Somehow, for more than 200 years, Cuba has managed to avoid being absorbed by the United States. That, in itself, is a remarkable achievement. Whether Cuba can chart a satisfying and reasonably prosperous future with the American leviathan brooding less than 90 miles away will be one of the most interesting questions of the second half of the 21st century.
Discover more on these topics at Listening to America
![Thomas Jefferson long harbored a desire to make Cuba part of the newly forming United States. In 1809, he wrote to James Madison outlining his dream to erect a column on the Southernmost limit of Cuba inscribed: "Ne plus ultra [i.e., thus far and no farther]."](https://ltamerica.org/wp-content/uploads/2025/02/jefferson-ne-plus-.jpg)
