I actually started this when there were no other posts in the thread...shows you how similar the ideas must run... and how long it took me (with interruptions) to get this far...
wikipedia said:
[T]he Republic of Cuba gained formal independence on 20 May 1902, with the independence leader Tomás Estrada Palma becoming the country’s first president. Under the new Cuban constitution, however, the U.S. retained the right to intervene in Cuban affairs and to supervise its finances and foreign relations. Under the Platt Amendment, Cuba also agreed to lease to the U.S. the naval base at Guantánamo Bay.
Independent Cuba soon ran into difficulties as a result of factional disputes and corruption among the small educated elite and the failure of the government to deal with the deep social problems left behind by the Spanish. In 1906, following disputed elections to choose Estrada Palma’s successor, an armed revolt broke out and the U.S. exercised its right of intervention. The country was placed under U.S. occupation and a U.S. governor took charge for three years. In 1908 self-government was restored when José Miguel Gómez was elected President, but the U.S. retained its supervision of Cuban affairs. Despite frequent outbreaks of disorder, however, constitutional government was maintained until 1925, when Gerardo Machado y Morales, having been elected President, suspended the constitution.
Machado was a Cuban nationalist and his regime had considerable local support despite its violent suppression of critics. During his tenure, Cubans gained greater control over their own economy and some important national development projects were undertaken. His hold on power was weakened by the Great Depression, which drove down the price of Cuba’s agricultural exports and caused widespread poverty. In August 1933, elements of the Cuban army staged a coup which deposed Machado.
This coup is the POD.
In OTL, the army installed Carlos Manuel de Céspedes as Cuba's new president. In this ATL, the army instead (after a brief period of restoring order and winnowing out perceived corrupt elements) returns José Miguel Gómez to power in January, 1934. Gómez is much loved by the people and promises to help Cuba emerge from its destitution. He is on good terms with the United States, and one of his first acts is to travel to Washington to meet with President Roosevelt and Congress.
Though the United States is still struggling with its own wrecked economy, Roosevelt (acting largely under the advice of envoy Sumner Welles) pushes through the "Good Neighbor Policy" in mid-1934, easing tariffs on Cuban products and relaxing travel and immigration policies between the two nations. Roosevelt encourages Gómez to use Cuba's natural resources to its best advantage, labeling the island "the land of sugar, sand and sun."
In return for American aid in constructing a more modern airport near Havana, Gómez grants the United States additional land on the island for the construction of a small military airbase.
News of the land grant is taken harshly by some elements in the government and army, who see the move as a huge step backward and an act of American imperialism. A coup, led by Gen. Fulgencio Batista, is attempted, but is quashed by government loyalists with the aid of American troops from Guantanamo. The coup leaders are imprisoned, but the rank and file soldiers are allowed to return to their duties; Gómez understands they are frustrated and poor, and that the need for American aid clashes with their nationalist pride. Gómez addresses the nation in the wake of the attempted coup and pleads for the nation's patience, reminding them that they are, and always will be, free Cubans.
By 1937, new American servicemen are manning the airbase, and new American money is flooding into the island nation as word spreads about its appeal as an inexpensive tourist destination. Growth is slow but steady, and the citizens' plight not so hopeless. In 1938, Gómez is returned to power in open elections.
The political stability within Cuba in the 1930s-1940s, coupled with its close relationship with the United States, allowed the island nation to emerge from the Great Depression on a path toward prosperity, not poverty. When the United States joined the war, Cuba, too, sided with the allies. American warships were common sights, and Cuba became both a strategic base for American submarines patrolling the Caribbean, and the most desired destination for sailors on leave.
Gómez left office in 1942, having given a lifetime of service to his country's quest for independence. He was succeeded by Eduardo Chibás, who pledged to continue Gómez's reforms and the modernization of Cuba. He launched a nationwide drive for literacy and improved education, drawing on American investors for support to build local schools, and encouraging an exchange program for American students and teachers to trade places with their Cuban counterparts in order to both foster stronger ties between the two nations and to encourage continued cultural (and economic!) investment.
Cuban rubber and sugar were crucial exports for the US war machine, and shrewd businessmen, such as Ángel Castro y Argiz, grew wealthy. In 1944, he sent his oldest son, Fidel, to study in the United States, at Yale University. A gifted, charismatic student, Fidel enrolled at Yale Law, where he excelled in everything he tried, earning top marks in class, a reputation as a ladies' man, and a starting spot on the Yale baseball team's pitching rotation.
With the end of the war, the American military presence in Cuba diminished somewhat, but the release of billions of dollars from the wartime economy meant commercial interests finally had a free hand in investing in the resource-rich island. Hoteliers and restaurateurs flocked to Havana and Manzanillo. Travel between America and Cuba was cheap and as easy as travel to Canada. As the island's economics turned from recovery to growth, many Cubans returned from the United States to their homeland, eager to find their fortune on native soil.
Fresh off a phenomenal 1947 season, pitching for a 25-4 record, Fidel Castro is offered a minor league contract by the Boston Red Sox. Much to his father's frustration, Castro accepts, and leaves Yale at the end of the Fall 1947 term. With pro baseball still recovering from the loss of many players due to the war, Castro is brought to the majors early in the 1948 season, where his charisma and deceptive hanging curveball earn him quick acclaim in Beantown.
The elections of 1948 bring both US President Truman and Cuban President Chibás back for another term. The rumblings of the communist threat do not escape either president's notice. Chibás cautions that while Cuban politics have been relatively stable for the past 14 years, he has not forgotten the volatility of the past. Truman quietly dispatches Sumner Welles to open a dialogue with the Cuban government about a plebiscite with the goal of bringing Cuban into the United States as an independent territory.
The next two years are a diplomatic rollercoaster for the two nations. Understandably, the Cuban people are proud of what their nation has been able to accomplish in the days since Gómez brought the government under control, but no one is foolish enough to ignore the crucial role that America played in helping Cuba succeed. American presence on the island is all-pervasive; the Cuban peso and American dollar are interchangable. The shops stock American foodstuffs, the people drive American cars. In America, the nation is distracted by the escalating crisis in Korea and the threat of communism at home. The Truman Doctrine guides American foreign policy; surely it makes more sense to bring Cuba under American protection NOW, rather than risk it fall to communist control and have to liberate it -- at god knows what cost now that the Russians have the bomb! -- in the future.
Having pitched the American League to victory in the 1950 All-Star Game, Fidel Castro is interviewed on CBS Radio. One of the journalists asks him his opinion about the plebiscite, and Castro jokes, "If it would help to bring a professional baseball team to Havana, I'm all for it!" The offhand remark is broadcast back in Cuba as well, where Castro is revered as the nation's greatest export (Desi Arnaz is a close second). Cuba is a nation obsessed with sport, and Castro is a constant reminder of Cuban pride operating within the American major leagues. A day later, Chibás shrewdly arranges a press conference, announcing a date for the plebiscite. He reminds the nation of Gómez's quote in the days after the failed coup, that no matter what, "We will always be Cubans."
On Sept. 1, 1950, the plebiscite passes by a dramatic 22 percent margin. American federal advisors descend on Havana, helping to speed the nation's transition. The process is beset with only minor obstacles, as Cuba's federal government had already been constructed similar to the American model. On Jan. 1, 1951, President Chibás was sworn in as the Cuban Governor-General, and every citizen of Cuba became a citizen of the United States, with all the rights and privileges thereunto.
In Boston, Castro is pitching the Red Sox to the top of the American League. "El Jefe" has the Sox off to a blistering start, going undefeated in his first eight starts and nearly throwing a no-hitter against the Tigers. Castro is on the hill against the Yankees on May 15, when tragedy strikes the gifted young hurler. Outfielder Hank Bauer connects on a fastball, sending the pitch straight back toward the mound. Castro lifts his hands to stop the line drive, but he misjudges the ball's velocity, and there's a sharp snap as the ball slams against his pitching hand. Castro drops like a stone, writhing in pain, and Fenway goes deathly silent. At second base, an astonished Bauer falls to his knees when he realizes what's happened. Castro is helped to his feet and led off the field. He will never pitch again. Without their staff ace, Boston plummets in the standings, to remain a perpetual non-contender for the next 35 years.
His pitching career over, Castro demurs at offers from the Red Sox to become a coach, and elects to complete his degree. Citing the support and generosity of the people of Boston, he enrolls at Harvard Law, and completes his degree in the summer of 1953. He is 27 years old. While he is courted by several firms eager to hitch their wagons to his celebrity, Castro is more interested in pursuing an advanced degree, or entering politics than working in an office. Tragedy would grant him this wish, just as it had cruelly robbed him of his pitching hand.
In October 1954, freshman senator John F. Kennedy undergoes back surgery to fuse several vertebrae, in an attempt to alleviate excruciating pain. But a post-surgical infection proves fatal to the handsome young Democrat. The district is thrown into disarray as a replacement for Kennedy is needed quickly. Party minders know, if given half a chance, that Joseph Kennedy will steamroll his next son, Robert, into the seat. Unwilling to acquiesce to Kennedy manipulation, Boston Democrats have a better idea: What about Castro? The handsome hurler has name recognition, celebrity, a Harvard degree, Bostonian credibility...and with his relative inexperience, he could prove susceptible to their influence. Castro is quickly wooed and won. The bastard born on a Cuban sugar plantation is living a dream, with wealth, fame and now a chance to hold the reins of power. How can he say no? When Congress reconvenes at the beginning of 1955, Sen. Fidel Castro (D-Mass.) is sworn into office. Bostonians and Cubans alike cheer for "our Jefe."
(whew...I've actually got to, y'know, do some work today. More later, if y'all want.)
) and then Castro becomes president in 1963.