In 1903, a significant agreement between the United States and Cuba reshaped the geopolitical landscape of the Caribbean, as President Theodore Roosevelt officially signed a lease for the area surrounding Guantanamo Bay. This pivotal moment stemmed from the aftermath of the Spanish-American War, which established the U.S. as a key player in Caribbean affairs. The terms of the agreement, part of the Platt Amendment, allowed the U.S. to occupy and develop the naval base at Guantanamo Bay, reflecting the American government’s interest in securing its influence in the region. Roosevelt’s intention was clear: to enhance U.S. naval capabilities and maintain a strategic foothold in the Caribbean, essential for protecting American interests and asserting dominance over maritime routes. The lease, across an initial area of 45 square miles, granted the U.S. extensive control while ostensibly assuring Cuban sovereignty. The financial terms were relatively modest—an annual rental of $2,000, which Cuba received but never fully acknowledged, creating a source of contention between the two nations. The agreement provided the U.S. with a crucial military base that would later gain prominence, especially during times of conflict such as World War II and the Cold War. While the Guantanamo Bay lease has played a vital role in U.S. military strategy, it also symbolizes a complex history of U.S.-Cuba relations, characterized by mutual distrust and contention. Over the years, the presence of U.S. forces in Guantanamo has sparked numerous debates regarding sovereignty, human rights, and international law, continuing to resonate in contemporary discussions about imperialism and interventionism. The agreement stands as a reminder of the intertwined destinies of the two nations, shaped by historical forces that linger to this day.