A History of Revolution
Columbus discovered Cuba on his first voyage in 1492, but it wasn't conquered until 1511 by Velasquez. Chris lied about its riches so that those who came first were adventurers seeking to extract quick wealth. Quickly it was discovered that it had no such riches but was a subtropical paradise in terms of soil and climate, which brought the monarch's favorite couriers with grants of huge estates.
Their real destiny was quickly established as a plantation economy and a naval refueling station. Immigrants brought disease and planter's brought death through overwork to the native "Indians" (poor Chris died thinking he had reached India). With the native labor supply exhausted, and the Spanish not wanting to work, African slaves were imported beginning in 1522. 
Until 1700, European powers and pirates periodically attacked the island. By 1764, Spain realized Cuba's agricultural potential (sugar, coffee) and began to both populate and administer it through colonial governors. Periodic prosperity resulted.
The nineteenth century was classic colonialism with growing pressures for independence. As in the Colonies, Cubans had no representation in the Spanish parliament (Cortes) yet their wealth was exploited and exported back to Spain under a mercantilist economic system operating to maximize Spain's wealth. A century of sporadic revolts, included a decade-long war of independence (1868-1878), and gradual abolition of slavery )1880-1895). Led in part by Antonio Maceo. [See card]
Cuba became an independent Republic after a final war of independence starting in 1892 under the leadership of poet Jose' Marti, Maceo, and others combining forces to fight the Spanish. The country was being destroyed by war when the U.S. offered to intervene as a mediator between the warring parties. Spain declined and when the U.S. Battleship Maine blew up in Havana harbor (Feb. 1898), public opinion in the U.S. demanded war with Spain. Theodore Roosevelt essentially created his own military unit and "stormed San Juan hill," gaining enough favorable publicity from the escapade to propel him to the presidency. The war also involved Admiral Dewey aboard the USS Olympia defeating the Spanish fleet in Manila Bay (May 1, 1898). Spain relinquished Cuba to the U.S. Dec. 10, 1898.
U.S. military occupation began in Jan. 1, 1899, ending in the Cuban constitutional convention, Feb. 1901. The U.S. imposed the Platt Amendment which granted the U.S. a lease for a naval station (Guantanamo, 1903) and the right to intervene in Cuban affairs in order to preserve Cuban independence. Several insurrections followed accompanied by U.S. intervention ending in 1909 with establishment of the Republic of Cuba.
From 1909 until 1925, a series of inept Cuban presidents headed governments characterized by corruption, nepotism, terror, and violence and an economy that alternated between prosperity and poverty. Beginning with his election in 1925, General Machado Morales became Cuba's first full-fledged dictator. With his re-election in 1928 a rule of terror began. As the Great Depression deepened, he adopted harsher methods building to a general strike in 1933 that forced him to flee.
Page 2 of 2 - Between 1933 and 1959 , Cuba had many presidents, but they were usually made and unmade by Fulgencio Batista, a sergeant who gained control of the army. The U.S. usually granted recognition of whatever military dictator prevailed in the latest coups. Batista was gone during WWII but came home to overthrow the government and return to power in 1948. He was elected in 1954 instigating a revolution. By 1959, Fidel Castro had come to power and Cuba began the switch from unequally-shared wealth to equally-shared poverty.
Next Week: Why Nations Fail: Summary and Conclusions
 Encyclopaedia Britannica, Chicago: U. of Chicago, 1966, Vol.6, pp.872-881.
 Maas, Peter, Crude World, NY: Alfred A. Knopf, 2009, pp6, 173,189, 207.