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The Naval Base at Guantanamo Bay has garnered significant attention since September 2001, but its significance in Western history began long before modern America. Christopher Columbus touched down in Guantanamo Bay in 1494, on his second voyage to the New World, searching unsuccessfully for gold. Despite the explorer’s disappointment, the discovery of the protected bay opened it as a safe haven for pirates and British Navy alike in the years that followed.

America’s interest came later, during the Spanish-American War in 1898, when a battalion of 647 Marines landed at Guantanamo Bay and tied down 7,000 Spanish troops in Guantanamo City, thus protecting Teddy Roosevelt’s charge up San Juan Hill 40 miles to the west. Like the British Navy before it, the U.S. Navy found the bay's protected waters useful, and in the treaty of 1903, the Cuban government agreed to lease defined areas around Guantanamo Bay to the U.S. for use as a naval station. This was the beginning of the oldest U.S. overseas base, and the only one (to eventually be) on Communist soil.

Signed by President Theodore Roosevelt, the initial lease enabled the US to contribute to the defense of Cuba through the maintenance of “coaling and naval stations.” A key element of this agreement was the passing to the United States of "complete jurisdiction and control over and within said areas." The only restrictions on the United States were that the area be used only as a coaling and naval station, and vessels engaged in trade with Cuba would retain free passage through the bay encompassed by the reservation. A subsequent agreement, signed by President Roosevelt on October 2, 1903, expanded on the initial lease, stipulating, among other things, a rent of two thousand dollars in gold each year, and that fugitives from Cuban justice, fleeing to the U.S. reservation, would be returned to Cuban authorities.

In the run up to World War II, the base expanded greatly. The stable acoustic conditions for echo ranging made the sea areas close to Guantanamo Bay ideal for training ships’ crew in anti-submarine warfare, and deploying convoys to the Southern Atlantic. Post-WWII, the Fleet Training Group was established to train Navy units, and the excellent amphibious training opportunities provided by adjacent islands led to staging of the 1st Marine Division at the Naval base. The Fleet Training Group was the bane of many a sailor -- the Navy’s version of finals and the SAT rolled into one. Liberty in town was a welcome respite for sailors who spent long tours underway, training under the demanding and often career-ending eye of the Fleet Training Group.The agreement, later confirmed by the Treaty of 1934 between the United States and Cuba, in effect gives the United States a perpetual lease on this reservation, capable of being voided only by our abandoning the area or by mutual agreement between the two countries. After taking power, Castro refused to recognize the treaty that established the base. He also refused to cash any of the U.S. checks after the Bay of Pigs Incident in 1961. The Castro government maintains that the perpetual lease provision of the Treaty of 1934 for the base is illegal.