Last week, U.S. President Barack Obama and Cuban President Raul Castro agreed to an exchange of prisoners being held on espionage charges. In addition, Washington and Havana agreed to hold discussions with the goal of establishing diplomatic relations between the two countries. No agreement was reached on ending the U.S. embargo on Cuba, a step that requires congressional approval.

It was a modest agreement, striking only because there was any agreement at all. U.S.-Cuba relations had been frozen for decades, with neither side prepared to make significant concessions or even first moves. The cause was partly the domestic politics of each country that made it easier to leave the relationship frozen. On the American side, a coalition of Cuban-Americans, conservatives and human rights advocates decrying Cuba’s record of human rights violations blocked the effort. On the Cuban side, enmity with the United States plays a pivotal role in legitimizing the communist regime. Not only was the government born out of opposition to American imperialism, but Havana also uses the ongoing U.S. embargo to explain Cuban economic failures. There was no external pressure compelling either side to accommodate the other, and there were substantial internal reasons to let the situation stay as it is.

The Cubans are now under some pressure to shift their policies. They have managed to survive the fall of the Soviet Union with some difficulty. They now face a more immediate problem: uncertainty in Venezuela. Caracas supplies oil to Cuba at deeply discounted prices. It is hard to tell just how close Cuba’s economy is to the edge, but there is no question that Venezuelan oil makes a significant difference. Venezuelan President Nicolas Maduro’s government is facing mounting unrest over economic failures. If the Venezuelan government falls, Cuba would lose one of its structural supports. Venezuela’s fate is far from certain, but Cuba must face the possibility of a worst-case scenario and shape openings. Opening to the United States makes sense in terms of regime preservation.

The U.S. reason for the shift is less clear. It makes political sense from Obama’s standpoint. First, ideologically, ending the embargo appeals to him. Second, he has few foreign policy successes to his credit. Normalizing relations with Cuba is something he might be able to achieve, since groups like the U.S. Chamber of Commerce favor normalization and will provide political cover in the Republican Party. But finally, and perhaps most important, the geopolitical foundations behind the American obsession with Cuba have for the most part evaporated, if not permanently than at least for the foreseeable future. Normalization of relations with Cuba no longer poses a strategic threat. To understand the U.S. response to Cuba in the past half century, understanding Cuba’s geopolitical challenge to the United States is important.

Cuba’s Strategic Value

The challenge dates back to the completion of the Louisiana Purchase by President Thomas Jefferson in 1803. The Territory of Louisiana had been owned by Spain for most of its history until it was ceded to France a few years before Napoleon sold it to the United States to help fund his war with the British. Jefferson saw Louisiana as essential to American national security in two ways: First, the U.S. population at the time was located primarily east of the Appalachians in a long strip running from New England to the Georgia-Florida border. It was extremely vulnerable to invasion with little room to retreat, as became evident in the War of 1812. Second, Jefferson had a vision of American prosperity built around farmers owning their own land, living as entrepreneurs rather than as serfs. Louisiana’s rich land, in the hands of immigrants to the United States, would generate the wealth that would build the country and provide the strategic depth to secure it.

What made Louisiana valuable was its river structure that would allow Midwestern farmers to ship their produce in barges to the Mississippi River and onward down to New Orleans. There the grain would be transferred to oceangoing vessels and shipped to Europe. This grain would make the Industrial Revolution possible in Britain, because the imports of mass quantities of food freed British farmers to work in urban industries.

In order for this to work, the United States needed to control the Ohio-Missouri-Mississippi river complex (including numerous other rivers), the mouth of the Mississippi, the Gulf of Mexico, and the exits into the Atlantic that ran between Cuba and Florida and between Cuba and Mexico. If this supply chain were broken at any point, the global consequences — and particularly the consequences for the United States — would be substantial. New Orleans remains the largest port for bulk shipments in the United States, still shipping grain to Europe and importing steel for American production.

For the Spaniards, the Louisiana Territory was a shield against U.S. incursions into Mexico and its rich silver mines, which provided a substantial portion of Spanish wealth. With Louisiana in American hands, these critical holdings were threatened. From the American point of view, Spain’s concern raised the possibility of Spanish interference with American trade. With Florida, Cuba and the Yucatan in Spanish hands, the Spaniards had the potential to interdict the flow of produce down the Mississippi.

Former President Andrew Jackson played the key role in Jeffersonian strategy. As a general, he waged the wars against the Seminole Indians in Florida and seized the territory from Spanish rule — and from the Seminoles. He defended New Orleans from British attack in 1814. When he became president, he saw that Mexico, now independent from Spain, represented the primary threat to the entire enterprise of mid-America. The border of Mexican Texas was on the Sabine River, only 193 kilometers (120 miles) from the Mississippi. Jackson, through his agent Sam Houston, encouraged a rising in Texas against the Mexicans that set the stage for annexation.

But Spanish Cuba remained the thorn in the side of the United States. The Florida and Yucatan straits were narrow. Although the Spaniards, even in their weakened state, might have been able to block U.S. trade routes, it was the British who worried the Americans most. Based in the Bahamas, near Cuba, the British, of many conflicting minds on the United States, could seize Cuba and impose an almost impregnable blockade, crippling the U.S. economy. The British depended on American grain, and it couldn’t be ruled out that they would seek to gain control over exports from the Midwest in order to guarantee their own economic security. The fear of British power helped define the Civil War and the decades afterward.

Cuba was the key. In the hands of a hostile foreign power, it was as effective a plug to the Mississippi as taking New Orleans. The weakness of the Spaniards frightened the Americans. Any powerful European power — the British or, after 1871, the Germans — could easily knock the Spaniards out of Cuba. And the United States, lacking a powerful navy, would not be able to cope. Seizing Cuba became an imperative of U.S. strategy. Theodore Roosevelt, who as president would oversee America’s emergence as a major naval power — and who helped ensure the construction of the Panama Canal, which was critical to a two-ocean navy — became the symbol of the U.S. seizure of

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