Christopher Columbus, on his first Spanish-sponsored voyage to the Americas in 1492, sailed south from what is now the Bahamas to explore the northeast coast of Cuba and the northern coast of Hispaniola. Columbus, who was searching for a route to India, believed Cuba to be a peninsula of the Asian mainland. The first sighting of a Spanish ship approaching Cuba was on 28 October 1492, probably at Bariay, Holguín Province, on the eastern point of Cuba.Gott, Richard (2004). Cuba: A new history. Yale University Press. Chapter 5.

During a second voyage in 1494, Columbus passed along the south coast of the island, landing at various inlets including what was to become Guantánamo Bay. With the Papal Bull of 1493, Pope Alexander VI commanded Spain to conquer, colonize and convert the pagans of the New World to Catholicism.Bakewell, Peter. A History of Latin America. Blackwell Publishers. pp. 129–130.

In 1992, Cuba declared itself a secular state and permitted Catholics and others to join the Communist Party. However, religious schools have remained closed since the early 1960s.

Before the Revolution

Historically, the foundations of the Catholic Church in Cuba were considered weaker than in the rest of Latin America. Spanish colonial authorities neglected Cuba and the local church served as "a colonial backwater dumping ground for miscreant clerics". The church also struggled with anti-clericalism in Cuba, further encouraged by the growth of Freemason circles and Protestant churches, many of them of anti-Catholic outlook. The role of the Catholic Church recovered in the late 16th century - the church became the main agency of welfare and education on the island, attempted to mediate conflicts, offered priesthood as a possibility for socioeconomic mobility to poor Cubans, and contributed towards founding Cuban national identity; many Catholic priests played an important role in the Cuban independence movement, such as Félix Varela. The peak of the Cuban Catholic Church as a social force was in the 1920s and 1930s, and many Catholic organisations and movements were established in that period, such as the la Juventud Cubana in 1927, Acciön Catölica in 1928, Caballeros Catölicos in 1929 and Agrupaciön Catölica Universitaria in 1931. As political parties of Marxist outlook and labour unions became common in the Cuban society, the Church established competing parties and trade unions to promote Catholic social doctrine instead.

As Fulgencio Batista came to power in Cuba through his 1952 coup, the response of the Catholic Church was negative, as "many religious leaders had judged the regime of Fulgencio Batista as unconstitutional, and were sick of finding bullet-ridden bodies in the streets". The church focused on evangelizing and assisting the rural population and urban lower classes, while also making humanitarian interventions on behalf of Batista's political opponents. The most famous instance of the church's intervention was the intercession of on behalf of Fidel Castro, following his failed attack on the Moncada barracks in 1953. Serantes made a public appeal to spare Castro and other perpetrators, and to give them as lenient sentences possible. According to Philip Rulon, this "was interpreted to mean that the majority church was sympathetic to the revolutionary movement" by the Cubans.

As the insurrection against Batista's regime escalated, the church attempted to mediate the conflict. Cuban cardinal Manuel Arteaga y Betancourt proposed a peace plan in 1956, ignored by the insurrectionists and the Batista regime alike. Afterwards the church hierarchy assumed an ambiguously pro-rebel stance, urging them to minimize violence while also criticizing Batista for his suppression of democracy. Cuban Catholics vigorously participated in the 26th of July Movement; many clerics and Catholic youth organised strikes and demonstrations, while also raising money for the insurrection. Members of Catholic social movements often joined the rebels, such as Manuel Artime. Already in 1956, as many as eleven chaplains were amongst anti-Batista rebels in the Oriente mountains. Priests who were part of the revolutionary movement wore "fatigue-green clerical apparel and accompanied the revolutionary band on as many of their missions as possible". Many of the revolutionary priests were Basque refugees from Spain, already "accustomed to political turmoil". The presence of Catholic clergy amongst the rebels provided a more moderate image of the rebels to the general population, as Castro countered the allegations of being a communist "by asserting that all the leader's men were good Catholics, and he even had several priests counted his forces". In addition, other Catholic priests indirectly assisted the rebels, requesting their parishioners to donate to the revolutionary movement, while also often serving as "recruiting officers". Both Batista and Castro acknowledged the contribution of the church towards the eventual revolution; Batista commented that he resigned "because of the opposition of the hacendados, colonos, the army and the church". Meanwhile, Castro declared that Cuban Catholics had given the revolution "very substantial assistance".

Fidel Castro

After the 1959 revolution, Cuba officially embraced atheism. Practicing Catholics and other believers were viewed with suspicion and discriminated against. Fidel Castro succeeded in reducing the Church's ability to work by deporting the archbishop and 150 Spanish priests, discriminating against Catholics in public life and education and refusing to accept them as members of the Communist Party of Cuba. The subsequent flight of 300,000 people from the island also helped to diminish the Church there.Chadwick, A History of Christianity (1995), p. 266

As the revolutionary regime came to power in January 1959, it enjoyed popular support and produced both revolutionary and nationalist sentiment. Following the revolution, the new regime was supported by the clergy, even if the degree varied. , the Archbishop of Santiago, called Castro an "exceptionally gifted man" and welcomed the new regime, while a progressive Franciscan magazine La Quincena celebrated the success of the revolution. At the same time, the church tried to discourage the revolutionary leaders from any affiliation with the Soviet Union. Over twenty letters were written by Cuban bishops between 1959 and 1961, urging the Castro regime to embrace a "Catholic form of socialism". Catholic magazines condemned Soviet communism as 'atheistic' while promoting papal criticism of capitalism, individualism and materialism, portraying Catholic social doctrine as a "third way" between the two opposing factions of the Cold War. A February 1959 issue of La Quincena was critical of the Cuban Communist Party, but praised the "social thought" of Castro and the leaders of the 26th July Movement. The magazine warned that the Communist Party was infiltrating worker unions and syndicates, such as the CTC. Even conservative Catholic newspapers such as Diario de la Marina cautiously embraced the revolution, praising "honest administration, and healthy and appropriate nationalism" of the revolutionary regime and declaring their support for it as long as it respected "Christian values" and acted within the boundaries of the Constitution of 1940.

As Fidel Castro visited the United States in April 1959, he reassured Vice President Richard Nixon that he was not a communist and only wished to pursue moderate reforms. Despite that, the Agrarian Reform Law was very extensive in scope, limiting land ownership to 1000 acres and nationalising larger holdings, which were later reorganised into state cooperatives. Nevertheless, the Bishop of Havana Evelio Díaz-Cía endorsed the reform as aligned with the Catholic teachings of social justice, while bishop Alberto Martín y Villaverde urged the government to "exercise a special preference on behalf of the rural peasants" in the reform, while describing the pre-revolutionary inequality of property and wealth in Cuba as a "grave evil".

Despite the initial support of the revolution, tensions started emerging between the new regime and the Catholic Church in late 1959. As the regime consolidated its power and took control of mass organisations, a break with both the United States and the Catholic Church in favour of a political realignment seemed inevitable. Despite previously supporting the land reform, Enrique Pérez Serantes now expressed concerns that it was going too far and pressured the regime to carry out a reform "in harmony with interested parties" instead. The climax of tensions between Castro and the clergy was marked by the National Catholic Congress on 30 November 1959."Cubans Roar Approval as Communism Is Condemned", Daytona Beach Morning Journal, November 30, 1959 During the congress, the attendees carried pictures of Our Lady of Charity, seen as "a quintessential symbol of Cuban identity".Montgomery, David. "Why the iconic Virgin of Charity means so much to Cubans and Pope Francis", The Washington Post, September 22, 2015 Bishops present asked Castro to let Catholicism provide "guiding ethical and moral values for the revolution", while José Ignacio Lazaga, the leader of the Catholic Youth Movement, said: "We believe that Catholic thinking on this subject can be summed up in this phrase: totalitarian states, no: social justice, yes." Fidel Castro denounced the Congress, accusing it of being a facade for attacks on the revolution.

The clergy was emboldened by the large turnout of the congress. Pérez Serantes considered it proof of Cubans being "Catholic people in the immense majority", although the large attendance could have also been caused by popular political anxiety about the direction of the revolution, in addition to support for Catholicism. Castro started harshly criticising the clergy, denouncing the clerical elite as "ambitious, egotistical, retrograde and predatory". The ideological clash between the Catholic Church and the revolutionary regime was particularly visible among the youth, where Catholic and Communist youth organisations strongly competed with each other. First violent confrontations between the revolutionary regime and the Catholic Church took place in July 1960, wounding several people, including a priest. In response, Bishop Eduardo Boza-Masvidal publicly attacked the regime for persecution of Catholics. However, Catholic newspapers remained relatively friendly, and La Quincena stated that Catholics of Cuba must upkeep the Christian elements within the revolution, praising it as "the first revolution that was inspired by Christian motives".