Cuba has been in the news with Obama's announcement of baby steps towards normalizing relations between America and Cuba. This is the outcome of a president's party getting thumped in a midterm election and desperately seeking anything to leave a legacy. I hope the Cubans in Florida get the message that the left no longer fears them in the quest for Florida's electoral votes. Even Cuban political action committees can be rendered useless due to Mexican immigration (Israel, you're next on the left's list). Most Americans, with a sense of history, know US-Cuban history in a few steps (nice timeline here). First, US beats Spain in a war to take over Cuba as a protectorate. Second, Castro overthrows the dictator. Third, the Bay of Pigs invasion fails in 1961. Fourth, the Cuban Missile Crisis occurs in 1962. Fifth, it turns into a craphole of communism that great baseball players escape from randomly. The missile crisis is the big historical touchstone because the reality of nuclear annihilation really hit Boomers with that crisis, and Boomers never let us forget anything about their youth. President Kennedy rode the white horse and protected America from those evil Russians during the Cuban Missile Crisis. America was just reacting to the Soviets being aggressors in our part of the world. Left out of history books is how the US created the Cuban Missile Crisis.
America's big brother relationship with Cuba kicked off with the Spanish-American War of 1898. While America's entry into that war is famously laid at the feet of William Randolf Hearst and his yellow journalism, one can easily glance at the front pages of many New York Times in the preceding year to read about valiant rebels in Cuba fighting evil Spanish governors. The last dying gasps of Spain's empire were during that conflict, leaving Spain to look inward and tear itself apart until a strong man emerged. This strong man issue popped up in Cuba's history. Cubans had rebellion in their blood as Hymen Roth joked in Godfather Part Two, "democracy" never quite worked well in Cuba and eventually a politician-military man, Fulgencio Batista, became dictator. Batista had been a powerful figure back in the early '30s, using his control of the army as a means for overall influence. This worked for him for a quarter of a century. Batista aligned with the wealthy economic interests, sugar, tourism, the American Mafia, and Cuba was a pretty swank island in the Caribbean.
But the USG system did not want a dictatorship just 90 miles from American shores. The student riots, the intellectual rebels, and the peasant rebels were too romantic for the left and the USG system to ignore. Batista was "repressive", killing or torturing anywhere from 1,000 to 20,000 people. A dictator such as him could not be supported by Americans with a good conscience. Batista though was a great ally for America. In the words of Ambassador Arthur Gardner, "I don't think we ever had a better friend". Gardner admitted Batista was getting a cut of the money pouring into Cuba, but Batista "was doing an amazing job". In March of 1958 Washington ended the sale of rifles and ended military aid to Batista, signing the order was General Eisenhower himself. This left Red Empire client Batista in a bind versus the homegrown rebels from a fighting standpoint. It is hard to defeat an illegal and violent insurgency with a dwindling weapon supply, just ask South Vietnamese President Nguyen Thieu.
Castro himself was a bit wishy-washy on the whole Marxism thing. In no speech before 1961 does the word "socialism" leave his lips. On the island itself in the '50s, the Cuban Communist Party thought that an uprising by the workers led by the Communist vanguard and not Castro's guerillas was the road to a Communist takeover. Per Vasili Mitrokhin, the Soviets only approved arms, thru the Czechs, for Castro on December 27, 1958, and they never even arrived in time for the Havana occupation. Pushing Castro, a lawyer by training, down the Communist road were his far more leftist brother Raul and Che Guevara. Those two men were the reliable communists in the eyes of the Soviets.
Setting up Batista for failure was a poor choice, but maybe not nearly as bad as the Eisenhower administration's handling of the January '59 overthrow. Batista had seen enough signs from the USG that he would not get support in a protracted struggle, and Castro's band of murderous merry revolutionaries took over Havana on New Years 1959. This was a confusing and dangerous time. Very quickly on January 7th, the Eisenhower administration recognized this group of rebels as the legal government of Cuba. Castro's revolution had very odd fighting with limited casualties on both sides that would not fill up an NBA arena. The USG jumped rather quickly to deem one side legitimate and the other side a useless relic, undeserving of any input. While saying he was not a communist, Castro was still the front man for a decidedly communist junta with his brother Raul and Che Guevera making steady contact with the Soviets. This was an incredibly stupid move because immediately after Castro's capture of Havana, a rebellion within the rebels started. It would last for six years and involve more troops, more deaths and a much more ruthless government military force than Castro's fight for power.
Like many "charismatic" thugs that take power Castro was seeking a means to cement his control, and not explicitly commie. Castro played a dual track outreach program with the US and USSR. Meeting with Vice President Nixon in the spring of 1959, Castro explained his reform ideas, and set into motion an American trade response that started to cut Cuba off from the US market. While the Soviets were still wary of Castro, American moves and his inner circle pushed him towards them. In the summer of 1959, Castro initiated contact with the Soviets, which over the course of 1959 set up a trade agreement. The Soviets bought 20% of all Cuban sugar exports, supplied them oil in trade and offered a $100 million low interest loan. These were large steps that became even more important with the 1960 US embargo on Cuba.
The year 1959 had other developments that created the Cuban Missile Crisis that had nothing to do directly with Cuba. In the fall of 1959, the US and Turkey signed an agreement that would deploy Jupiter nuclear missiles in Turkey. These missiles would have to fly the short trip over the Black Sea to strike on Soviet territory. If a missile defense shield site in Poland bothers the Russians now, nuclear missiles in Turkey would justifiably send the Soviets into a rage. This choice of missile deployment was a bit odd, since the military had the "around the clock" armed bombers patrolling the skies as a deterrent and had just launched ballistic missile carrying submarines in 1958 with more to follow. The Jupiters were obsolete by the time they were placed in Turkey, yet the US still went forward. This move was just asking the Soviets to look for an in, and they found one.
The final chess move that failed CIA project to topple Castro that Americans know as the Bay of Pigs invasion. There were holes in preparation, but President Kennedy would not send in the air cover. Had he known what Nixon would learn in the '70s and the US would use to decisive effect starting in the '90s about air supremacy and close ground support ruling the battlefield, Kennedy would have pulled the trigger. The air power if you provide the boots on the ground is a formula the US is using to this day. The US just did not understand the power of air support in 1961, and looking at the AIr Force's smearing of the A-10 Warthog, it is biased against it today. This failed invasion solidified Castro's support despite not delivering on promises, and pushed Castro deeper into the Soviet embrace. That Soviet protection and trade would come with a cost, and the Soviets and Cubans agreed to building ballistic missile bases in Cuba. The construction of these bases would set up the Cuban Missile Crisis. Americans could beat their chests and say they went "eyeball to eyeball and the other guy blinked".
As we can see, the good guy Kennedy administration was not really reacting to bad guy Soviets slipping nuclear missiles in America's backyard. President Kennedy and his team of the best and brightest had a crisis management style where their foreign policy was really just jumping from one problem to the next with no grand theme. The Cuban Missile Crisis cannot be laid at their feet though as this moment in history was a result of multiple goofs by the USG system. The doves and liberal elements of the foreign policy system did not like Batista and he had to go. The US immediately recognized a ragtag band of rebels with a tenuous hold on the capital in a Civil War. The US placed nuclear missiles right under the belly of the Soviets despite simultaneously starting the program that would guarantee American nuclear safety for fifty years (ballistic carrying submarines). When the US saw a chance to topple the little tyrant, it could not finish the job. The US then stopped all support for the actual rebellion remaining on the island. The left can tsk-tsk modern America and say that our actions in the Middle East brought 9/11 on ourselves, yet none will look at that island just to our south and think of the moment the US nearly faced nuclear annihilation (besides the suffering inflicted on Cubans) as blowback for a series of decisions.