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It was 1935, and the Guantánamo naval base had to go. So declared an American commission stocked with foreign-policy experts: the United States was pursuing less antagonistic relations with its southern neighbors, and an American base on Cuban soil, anchored by a lease without an end date, looked increasingly like an “anomaly.” Weren’t there enough defensible harbors on the United States’ own Gulf Coast, or on Puerto Rico? The commission wrote that the U.S. government should “seriously consider whether the retention of Guantánamo will not cost more in political misunderstanding than it is worth in military strategy.”

Where was the base? This was a trickier question than might first appear. It straddled both sides of lower Guantánamo Bay, roughly five hundred miles east and south of Havana, about as far from the capital as one could travel and remain in Cuba. The bay opened onto the Windward Passage, one of the hemisphere’s most trafficked sea-lanes, linking the Eastern Seaboard to the Gulf of Mexico, Central and South America, and, through the Panama Canal, the Pacific Ocean. In 1899, an American military planner, stressing the need for naval bases and coaling stations in Cuba, had called the island “an outer bar of the Mississippi.”

The terrain that rose above the bay—dry, sun-blasted hills, where cactus and scrub clung to outcroppings of barren rock—was hostile enough that Cuba’s Spanish rulers had taken their time colonizing the region. For centuries, Guantánamo had effectively been no state’s domain, a haven for pirates and slaves escaping both Cuba and Haiti, only a hundred miles across the Windward Passage at its nearest point. For them, Guantánamo had meant something like freedom.

The more perplexing question was where the base stood legally. By the late nineteenth century, U.S. commercial and military interests in Cuba and the wider Caribbean had deepened. When a Cuban uprising against Spanish control threatened to secure the island’s independence, American policymakers pursued military intervention, capitalizing on popular outrage at the mysterious explosion of the U.S.S. Maine, in Havana harbor, in February of 1898. In a nine-day battle for Guantánamo Bay, American soldiers, under Commander Bowman H. McCalla, and Cuban insurgents defeated the Spanish garrison. In June, the Cuban diplomat Manuel Sanguily wrote to a friend, “Now that they have seen Guantánamo, they will never renounce their control over it.”

He was not far off. The United States took possession of Guantánamo Bay through what might be called gunboat tenancy. While Cuba’s constitutional convention gathered in late 1900 and early 1901, Secretary of War Elihu Root listed provisions that “the people of Cuba should desire” for their constitution; these included granting the United States the right to intervene freely in Cuban affairs and access to land for naval bases. These demands went into the Platt Amendment, passed by the U.S. Senate on March 1, 1901, and submitted to the convention for adoption; the United States would withdraw its forces from the island only after the delegates incorporated it into their constitution. Cubans opposed the Platt Amendment in speech, pamphlet, and mass protest; Juan Gualberto Gómez, a delegate and a former general, charged that it would transform Cubans into a “vassal people.” Nevertheless, under pressure a divided convention adopted it.

The U.S. Navy moved quickly. Two 1903 agreements gave the United States control of forty-five square miles of land and water—a space about two-thirds the size of Washington, D.C.—for coaling and naval stations “and for no other purpose.” Rent was $2,000 a year, paid in gold; lacking a cutoff date, the lease was “for the time required.”

The terms were ambiguous from the start. Cuba retained “ultimate sovereignty,” for example, but the United States exercised “complete jurisdiction and control.” A second lease, signed in 1934, similarly embraced uncertainty. It raised the rent to $4,085, but provided no termination date. The agreement could be ended by American withdrawal or by a bilateral settlement, but not by Cuban action alone. The Navy had sprawled onto a thousand or so additional acres, but the new agreement did not say where they were: the base would continue occupying “the territorial area that it now has.”

At noon on December 10, 1903, the United States assumed “complete jurisdiction and control.” A marine brigade, five naval companies, and a few Cubans looked on as the Stars and Stripes was hoisted to a twenty-one-gun salute. The American Minister stayed home, as did high-ranking Cuban officials. The Atlanta Constitution noted that most Cubans “were not inclined to sanction by their presence an act which they chose to consider was unjustly imposed on them.”

Some Americans questioned the United States’ imposition of power beyond its borders. What would be the legal status of these newly conquered territories? Supreme Court Justice Melville Weston Fuller, dissenting in the 1901 Downes v. Bidwell case on the status of Puerto Rico, had warned that “if an organized and settled province of another sovereignty is acquired by the United States,” Congress would retain the power “to keep it, like a disembodied shade, in an intermediate state of ambiguous existence for an indefinite period.”

Others were more sanguine. As Woodrow Wilson, who was the president of Princeton at the time, put it in an April, 1907, address, “Colonies must be obtained or planted, in order that no useful corner of the world may be overlooked or left unused.” The corollary to this imperial proposition: once you wrested turf from somebody else, you found something to do with it.

But during the next thirty years U.S. officials failed to make the Guantánamo base as useful as they had hoped. Congressmen wanted to spend naval funds on bases near their constituents. Fresh water had to be brought from Guantánamo City, hauled in railroad tanks to Navy barges, then pumped into storage tanks. “Here we are ensconced in Guantánamo Bay for ten years,” the American journalist Stephen Bonsal complained in 1912, “and we have not raised a finger to fortify what the Russians or the Japanese, or any other predatory people, would immediately convert into a great naval station and citadel and proudly christen ‘Mistress of the Caribbean.’ ”

It was not that the base went unused. It hosted naval exercises and drills, and it resupplied U.S. vessels. The roughly twenty-year U.S. occupations of both Haiti and the Dominican Republic commenced with invasions from Guantánamo. The base was also useful to thousands of Cuban laborers who earned their livelihood on its wharfs and in its machine shops and warehouses.

While the boundaries of the base were indefinite, it was, in the twenties and early thirties, clearly outside the precincts of Prohibition. Officers stocked up on alcohol from Cuban suppliers. Sailors crammed bars in Caimanera and Guantánamo City, seeking rum and economically vulnerable women; this was called “liberty.” For many, the base was a weird cocktail of dull heat, lassitude, and excess. Morally and geographically, it was, one visitor wrote, “on the fringes of things.”

The Second World War rescued the base. A hub in the United States’ Caribbean convoy system, by the mid-nineteen-forties, it was the second-busiest port in the Western Hemisphere, after New York. Franklin D. Roosevelt himself visited twice in two years. (Harry Truman also stopped by, seasick, in 1948.) The base acquired the nickname Gitmo, from the Navy call signal GTMO; sailors boasting of their access to Cuban women jested that it was not called “git’ mo’ ” for nothing.