I just read The Duke of Havana: Baseball, Cuba, and the Search for the American Dream, by Steve Fainaru and Ray Sánchez. I enjoyed it immensely, and would highly recommend it for anyone interested in baseball and Cuba. It's now on my sidebar list.
It tells the story of Orlando “El Duque” Hernández, who defected from Cuba in late 1997, and who was a huge baseball star there. His brother, Liván, had defected the previous year, which created a stampede mentality as Cuba players sought to get out and sign huge deals with major league teams in the U.S. An almost hyperactive would-be agent followed the Cuban teams all over the place, trying to convince players to defect.
Ultimately, the Cuban government banished El Duque from all official levels of play, saying his association with such people (and with his brother) made him a bad example for revolutionary baseball—he was forced to play sandlot games. It was this that sparked the chain of events that would eventually bring him to the New York Yankees and the 1998 World Series (unfortunately, against the Padres). It’s a remarkable story.
Throughout, the book is highly critical of Cuban politics, especially the combination of total power and arbitrariness. With no explanation, your livelihood is taken away. Once you are labeled as a counter-revolutionary, then you are largely shunned and you have to struggle even harder to make ends meet. At the same time, however, it also highlights the shaky promise of major league baseball, and capitalism in general. Once spirited out of Cuba, the players would try out (Costa Rica was a popular destination—the players needed to establish residency in another country in order to be free agents). If they didn’t cut the mustard, then they were tossed aside, to the vagaries of a capitalist system they did not understand. If they weren’t good enough, then immediately no one cared whether they starved or not.
El Duque himself admitted that he did not defect because of dissatisfaction with life in Cuba—in fact, everyone discusses being poor, but this does not lead to a desire to leave their homes and families. El Duque’s family was very ambivalent about following him to the U.S. Instead, he left because he had been banned from baseball—if the Cuban government hadn’t gone that far, he might have stayed. The book ends with a discussion between several Cuban émigrés, and some of them wondered whether they would’ve been better off in Cuba.
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