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The Spanish-American War began in 1898, with the US intervening in the Cuban War for Independence. The explosion of the USS Maine in Havana harbor precipitated U.S. involvement. Cuba gained formal independence from Spain following the war's conclusion in December 1898, as per the Treaty of Paris. However, the Platt Amendment of 1901 ensured Cuba remained under US influence. The war was significant for ending Spanish colonial rule in the Americas.

The collapse of the Soviet Union in 1991 had a profound impact on Cuba, as it marked the end of substantial Soviet economic support. This plunged Cuba into a severe economic crisis known as the 'Special Period', characterized by shortages of food and fuel, which necessitated austerity measures and the opening of the economy to some foreign investment and tourism. This event forced Cuba to become more self-reliant and adapt its socialist model.

Christopher Columbus landed on the northeastern coast of Cuba on October 28, 1492, during his first voyage across the Atlantic. This marked the beginning of Spanish exploration and colonization of the island, which would last for nearly 400 years. This event is significant as it brought Cuba into the Spanish Empire, leading to significant cultural and demographic changes due to colonial rule and the introduction of African slavery.

Former Cuban President Fidel Castro died on November 25, 2016. As the primary leader of the Cuban Revolution and the head of state for nearly half a century, his death marked the end of an era for Cuba. Fidel Castro was a polarizing figure, revered by some for his resistance against imperialism and denounced by others for human rights abuses. His death prompted discussions on the potential for political and economic changes in Cuba.

On January 1, 2020, Cuba ended its dual currency system, unifying the Cuban peso (CUP) and the convertible peso (CUC). The dual system existed since the 1990s as a part of special economic measures during the 'Special Period'. The unification was intended to simplify commerce and address economic disparities, but it also caused inflation and short-term economic difficulties for many Cubans. This policy change aimed to create a more comprehensive and efficient economic structure.

Raúl Castro officially took over as President of Cuba on February 24, 2008, succeeding his brother Fidel Castro. Raúl's presidency marked a shift towards more pragmatic economic policies, including gradual liberalization allowing for small private businesses and increased foreign investment. He also pursued a historic reopening of diplomatic relations with the United States. His governance was key in slowly reforming Cuba's economy and international relations.

In July 2021, Cuba experienced the largest protests in decades, triggered by severe economic crises, the government's handling of the COVID-19 pandemic, and demands for political reforms. These demonstrations revealed widespread dissatisfaction with the government amid deepening economic hardships. The government's response included internet blackouts and arrests, leading to international condemnation and a renewed focus on Cuba's human rights record and governance.

A new Cuban constitution was adopted following a national referendum on February 24, 2019. The constitution introduced several changes, such as recognizing private property, limiting presidential terms, and introducing the role of Prime Minister. This reform was an attempt to modernize the Cuban political and economic system while maintaining the socialist character of the state. The approval of the new constitution suggests a controlled process of transformation in Cuba's system.

The Communist Party of Cuba was officially founded on August 16, 1925. Despite varying levels of influence and repression across different political eras, it became the ruling party after the 1959 Cuban Revolution. Under the leadership of figures like Fidel Castro and Raul Castro, the Communist Party has directed Cuba's socialist policies, centralized economic planning, and one-party political system, making it a fundamental institution in Cuban governance.

The Bay of Pigs Invasion, launched on April 17, 1961, was a failed military invasion of Cuba by Cuban exiles sponsored by the US CIA. The aim was to overthrow Fidel Castro's communist government. The invaders were defeated within three days. It was a significant event as it embarrassed the U.S., solidified Castro's rule, and paved the way for Cuba's closer ties with the Soviet Union.

Cuba's current constitution was enacted on February 24, 1976, following a popular referendum. It established a Marxist-Leninist framework for the state and government, cementing the Communist Party's role as the only legal political party in Cuba. This constitution emphasized socialist economic property and entitled citizens to free healthcare and education, laying the foundation for Cuba's current political and social structure.

On July 20, 2015, Cuba and the United States officially re-established diplomatic relations, previously severed in 1961, by reopening embassies in each other's capitals. This move was part of the broader process of normalizing bilateral relations under the Obama administration. The reopening of embassies was an important symbolic step in rebuilding official diplomatic communication and cooperation between the US and Cuba.

The Ten Years' War was the first major Cuban insurgency against Spanish rule, starting on October 10, 1868. It was led by planter Carlos Manuel de Céspedes, who freed his slaves and declared Cuban independence. The war ended in a truce with Spain promising reforms, many of which were not implemented. This war is noteworthy as it set the stage for Cuban independence struggle and the abolition of slavery.

In December 2014, US President Barack Obama and Cuban President Raúl Castro announced the beginning of a process to normalize relations between the two countries. This included the easing of travel restrictions, the restoration of embassies, and the removal of Cuba from the US list of state sponsors of terrorism. This détente marked a significant departure from over half a century of hostility following the Cuban Revolution.

Diego Velázquez de Cuéllar led the Spanish conquest and settlement of Cuba starting in 1511, establishing Baracoa, the first Spanish settlement on the island. Over the following years, other settlements like Santiago de Cuba and Havana were founded. This set the course for the Spanish colonial economic and administrative systems, which relied heavily on indigenous labor and later African slaves for plantation agriculture and mining.

In 2002, in the wake of the 9/11 attacks, the US established a detention camp at its military base in Guantanamo Bay, Cuba, to hold terrorism suspects. The camp has been criticized internationally for human rights abuses and the legal status of detainees. Cuba has repeatedly objected to the presence of the base, highlighting issues of sovereignty and legal jurisdiction. Guantanamo Bay has become a point of tension in US-Cuban relations and debate over international law and human rights.

The Cuban Revolution culminated on January 1, 1959, when Fidel Castro's guerrilla forces overthrew the US-backed dictator Fulgencio Batista. The revolution transformed Cuba into a communist state, leading to significant social reforms but also political repression. This marked a significant turning point in Cuban history and Cold War politics, as Cuba aligned with the Soviet Union, prompting the US to impose an ongoing economic embargo.

The Cuban Missile Crisis, in October 1962, was a 13-day standoff between the United States and the Soviet Union over Soviet ballistic missiles deployed in Cuba. It is regarded as the closest the Cold War came to escalating into a full-scale nuclear war. The crisis ended when the Soviets agreed to withdraw their missiles in exchange for US promises not to invade Cuba and to secretly remove US missiles from Turkey.

The Cuban War for Independence began on February 24, 1895, led by José Martí and the Cuban Revolutionary Party. This war aimed to achieve Cuba's independence from Spanish rule and featured tactics such as guerrilla warfare. Although Martí died early in the conflict, the war persisted until it merged into the Spanish-American War in 1898. This war is key to understanding Cuba's journey towards independence and national identity.