Castillo was born in Ciego de Ávila, a city located in the central part of Cuba and the capital of Ciego de Ávila Province. At age 22, he showed enough skills to land a spot on Los Tigres, the nickname for Ciego de Ávila\'s club in the Cuban National Series. Additionally, he played with the Cuban national baseball team in several international tournaments, including the 2011 Baseball World Cup and the 2011 Pan American Games, before defecting from Cuba in December 2013 to pursue a Major League Baseball career. Castillo signed a $72.5 million contract with the Boston Red Sox on August 23, 2014, which runs through 2020.\n', '

Castillo joined the Ciego de Ávila team in the 2008–2009 season, playing for them through 2012–2013. Used sparingly during his first two seasons, he played only 28 games in his rookie year and 44 as a sophomore, while hitting averages of .349 (15-for-43) and .303 (30-for-99), respectively. He spent most of his time playing second base, third base, and the corner outfield positions, until becoming a solid center fielder in the years to come.\n', '

His breakout season came in 2010–2011, when he got a major boost in playing time and posted a .320 average with 22 home runs and 95 runs batted in in 107 games, including 75 runs scored, 27 doubles, five triples, and a league-lead 32 stolen bases.\n', '

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