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IN APRIL PRESIDENT OBAMA shook hands with Raul Castro, president of communist Cuba, at the Summit of the Americas in Panama. The two later sat down for a discussion—the first such meeting between American and Cuban leaders since the revolution led by Raul’s older brother Fidel in 1959. Days after the Panama summit, the White House announced that the State Department would remove Cuba from its list of state sponsors of terrorism.

President Obama explained that he was trying to surmount a troubled past. “I’m not interested in having battles that, frankly, started before I was born,” he said. Obama might not be interested in them, but battles over Cuba have run through American history for almost 200 years. For most of that time the United States favored Cuban independence, so long as Cuba was stable and friendly. Yet numerous invasions of Cuba have been launched from American soil—by private adventurers, disgruntled Cubans and the U.S. government itself—and Cuba has been occupied several times by American troops. Cuba, the closest Caribbean island to the United States, may be too close for comfort.

Columbus claimed Cuba in 1492, the first building block of Spain’s New World empire. But by the early 1820s most of Spain’s possessions had won their independence. What would become of Cuba? In a letter to President James Monroe in 1823, Thomas Jefferson said he considered the island “the most interesting addition which could ever be made to our system of States.” Monroe’s secretary of state, John Quincy Adams, agreed: “There are laws of political as well as of physical gravitation. . . .Disjoined from its own unnatural connection with Spain, [Cuba] can gravitate only towards the North American Union.”

These early designs on Cuba became entangled with the politics of slavery. Southerners coveted Cuba as a potential slave state. Some Cuban sugar planters, fearful that a weak Spain might succumb to abolitionist pressure from Britain, were willing to be annexed by a stronger slaveholding power. But the U.S. government was worried about violent upheaval in Cuba—in the chaos of a pro-American revolution or an invasion, local slaves might rise up as they had in Haiti in 1791—so Democratic presidents from Polk to Buchanan tried instead to buy it, offering Spain as much as $130 million.

Reckless souls in both the United States and Cuba nevertheless hoped to settle Cuba’s future by force. Narciso Lopez, a rebellious Spanish general, plotted a private invasion of the island by Cuban and American adventurers—an action known in the early 19th century as filibustering. (The meaning of “filibuster” as a long, obstructive speech is a later one.) Lopez offered the command to three veterans of the Mexican War: Robert E. Lee, Mississippi senator Jefferson Davis and Mississippi governor John Quitman. When they refused, he led the operation himself. In 1851 loyal Spaniards captured him west of Havana, and he was executed. All that remains of his efforts is the flag he designed—a visual riff on Old Glory with a white star in a red triangle, and blue and white stripes—which flies over Cuba to this day.

The United States remained interested in Cuba after the Civil War. Cuban patriots, backed by exiles in New York, launched a war of independence in 1868. President Ulysses Grant offered to pay Spain $100 million to let Cuba go free; Spain countered by asking for $125 million. Nothing came of the negotiation because American sympathies were mixed: Both sides in the war were committing atrocities, and the Cuban rebels had no clear policy on slavery (some were abolitionists, others were slave owners). Grant was also distracted by a vain effort to annex the Dominican Republic as a home for American freedmen. The Cuban war dragged on until 1878 and ended with Spain still in charge.

Cuban patriots rebelled again in 1895, supported by exiles in New York and Tampa. Slavery was no longer an issue; Spain had abolished it in 1886. The new rebels were welcomed by a new breed of American expansionist led by Senator Henry Cabot Lodge of Massachusetts; Lodge’s former teacher, the historian Henry Adams; and Theodore Roosevelt, who became assistant secretary of the Navy in 1896. The expansionists wanted secure approaches to a Central American canal. That, they believed, meant ending incompetent and despotic Spanish rule in Cuba. “Our own direct interests” in Cuba “were great,” as Roosevelt put it. “But even greater were our interests from the standpoint of humanity.” President William McKinley tried, like Grant, to buy Cuba’s freedom, offering as much as $300 million. But in February 1898 the USS Maine blew up in Havana Harbor, killing more than 260 sailors. Blaming the explosion on Spanish sabotage (a 1974 Navy study concluded that the explosion was accidental), an enraged America declared war in April; Cuba was conquered by August.

The United States did not intend to stay. Its declaration of war had been accompanied by an amendment promising self-rule to Cuba, and American troops left in 1902. But it also wanted self-rule to be orderly—and, given the nature of Cuban politics, that seemed to require frequent intervention. Theodore Roosevelt, now president, sent troops back to Cuba after a 1906 revolution. His cousin Franklin, president in 1933, foreswore big-stick diplomacy, promising instead to be a good neighbor to Cuba and other Latin American countries. Yet even FDR’s ambassadors massaged a series of Cuban revolutions until a government acceptable to the United States came to power.

Cuban politics stabilized around two dictators. Fulgencio Batista, a leader of the military coup that deposed the government in 1933, was in and out of office until 1959. Batista was first elected with the support of Cuba’s Communist Party, though he soon became pro-Ameri-can. Fidel Castro was a radical activist who drove Batista from power. Castro initially denied that he was anti-American or a communist, but a year after coming to power, he gave Anastas Mikoyan, deputy premier of the Soviet Union, a hero’s welcome in Havana. President Dwight Eisenhower authorized a CIA plan to train Cuban exiles, and in 1961 the CIA landed 1,400 of them at Cuba’s Bay of Pigs. The United States did not give these green troops air cover, however, and Castro’s army mopped them up. Cuban-American relations for the next 30 years were subsumed in the Cold War.

And now? The Cold War ended with the fall of the Soviet Union in 1991, but the Castro regime marches on. In 2008, 81-year-old Fidel was succeeded as president by his younger brother Raul. Among modern political dynasties, only the Kim family of North Korea has ruled longer, and they span three generations.

Obama has opened a new chapter in Cuban-American relations, but not necessarily the final one. As has been true since the days of Narciso Lopez, the government of Cuba has powerful American critics. Three senators who blasted Obama’s rapprochement—Robert Menendez, D-N.J.; Marco Rubio, R-Fla.; and Ted Cruz, R-Texas—have Cuban roots: Menendez’s and Rubio’s parents and Cruz’s father all fled Cuba for the United States in the 1950s. Both Rubio and Cruz hope to succeed Obama in the White House.

John Quincy Adams was right: The North American Union exerts a powerful pull on its island neighbor. But the goals of Cuban independence and stability as the United States defines them do not always align. America intervenes in Cuban affairs, often ham-handedly, which provokes Cuban resentment—virulent in the case of the Castro brothers. Solid Cuban-American friendship seems as elusive as Cuban freedom.


Originally published in the October 2015 issue of American History magazine.