Thomas Jefferson described Cuba as "a fruit that will soon fall into our hands." His prophesy began to come true in the 1860s. The U.S. was already Cuba's most important market and source of imports, especially food. After civil war cut the northern states off from the southern states' sugar the U.S. imported 80% of Cuba's sugar harvest. In 1868 Cuba's first war of independence began under José Martí, the father of Cuban nationalism. During this war and the second one led by Antonio Maceo, American mercenaries paid by U.S. sugar importers guarded sugar mills and other assets. By the time the U.S. entered the war in 1890 the rebels were winning, Antonio Maceo had refused to make any settlement short of complete independence, and U.S. interest owned most of Cuba's sugar industry. The U.S. military occupation sold the prime sugar lands to these interests for pennies an acre.
The new Republic of Cuba was required by the U.S. Congress to add the Platte Amendment to their constitution in order to end the U.S. occupation. The amendment gave the U.S. unlimited rights to establish military and naval bases in Cuba and to invade Cuba for the purpose of "restoring order." Economic value aside, Cuba was an important asset for countering the naval presence of Britain, the United States' rival for domination of Latin America. The United States repeatedly invaded Cuba to keep it safe for U.S. property and Washington supported dictators who did that work for them. The last of these was Fulgencio Batista who led the military coup of 1952.
Batista formed a partnership with the Mafia. Ciudad La Habana became the best little narco-trafficking base, money laundering center, and whorehouse in the Caribbean. So notorious was Batista's corruption that it was politically impossible to shed American blood to save him. Still the Eisenhower administration gave Batista what help they could against Fidel Castro's guerrillas in the Sierra Maestra. Batista's planes even landed at the Guantanimo Bay Naval Base to receive fuel and bombs. By the 1950s U.S. corporations owned 80% of Cuba's land, most of the sugar industry, and all of the public utilities, oil refining, nickel industry and railroads.
When the revolution triumphed in December 1959 the attitude of Washington and of Cuba's literate .8% was wait and see. The insurrection that brought down the Machado dictatorship in 1933 had led only to a change of self serving masters who did not threaten U.S. investments or the social pyramid.
Then in 1960 the Castro junta passed the Urban Reform Law limiting the amount of urban real estate that any natural person or corporation could hold. Assets above the limit were nationalized. The U.S. cut Cuba's sugar quota. Then came the Rural Reform Law limiting the amount of farm land an individual or corporation could own. Castro's own family lost land. Cuban elites including most physicians and other learned professionals turned against the revolution and left for Florida. Washington cut off Cuba's oil, their only fuel, and prevented Cuba from obtaining oil elsewhere except the Soviet Union. When Standard Oil refused to refine Soviet crude, Castro nationalized their refineries. But Washington did not break trade relations with Cuba.
Then came the Cuban Missile Crisis immediately after the failure of the Bay of Pigs invasion-recruited Pro-Cuban expatriates, trained in Florida, launched from Somosa's Nicaragua, and engineered by CIA. Squadrons of unmarked B-26s bombed Cuba for the invaders, but U.S. fighter planes stayed on the ground and U.S. war ships, massed off Cuba's shores, did not engage. President Kennedy was severely criticized for this.
Part of the settlement to the Cuban Missile Crisis of 1962 was Kennedy's pledge that U.S. forces would not invade Cuba. Instead there was a CIA dirty war using crop, livestock and human disease. Fields were burnt, assets were destroyed and people were murdered. But the economic blockade was the greater impediment to development costing $60 billion by 1989.