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 and.303, 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. 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. Castillo enjoyed another fine season in 2011–2012, as he batted.342 and slugged.574 in 113 games, stealing 27 bases and collecting a very solid.408 on-base percentage, while driving in 84 runs and scoring 101 times. In addition, he topped the league with 37 doubles, ranked 13th in batting average and tied for third in stolen bases. Castillo played his last season in 2012–2013. But this time his batting average declined to.274, as well as his games played, going 64-for-234 with six homers, 29 RBI and 15 stolen bases.
International competition
In between, Castillo gained prominence as a member of the Cuban national baseball squad. With Yoenis Céspedes and Leonys Martín gone from Cuba, he became the regular center fielder for his team in the 2011 Baseball World Cup held in Panama. Castillo was named to the tournament’s All-Star team after leading the World Cup in batting average and slugging while ranking fourth in on-base percentage. Overall, he went 21-for-41 with four doubles, two triples and two homers in 10 games. Castillo also played in the 2011 Pan American Games hosted by Mexico, where he hit.273 and slugged.318 with a.333 OBP. In the same year, he played in the World Port Tournament in the Netherlands. Then, in 2012 he appeared in exhibition baseball series held at Nicaragua, Taiwan, Japan and Cuba, where he faced the U.S. College National Team, in preparation for the upcoming 2013 World Baseball Classic. Castillo was originally slated to be part of the team, but he did not make the final cut. According to an official statement released, he was suspended for trying to defect. As the Havana Times reports, a pattern has developed especially over the last decade whereby Cuban baseball stars and top prospects attempt to leave the island illegally and are caught and suspended from playing in the Cuban league. With no choice left to them to continue in their profession, they then succeed at a future attempt escaping to a neighboring country. Finally, Castillo attempted to leave Cuba once more, and was successful. In early June 2014, he was granted official free agent status by Major League Baseball after establishing permanent residency in the Dominican Republic and being unblocked by the Office of Foreign Assets Control.
Major League Baseball career
Boston Red Sox
On August 23, 2014, the Boston Red Sox signed Castillo to a seven-year, $72.5 million contract. Castillo was given the jersey number, 38, he wore in Cuba.
2014
Castillo made his major league debut on September 17, 2014, as the Red Sox starting center fielder; he collected his first MLB hit in the fourth inning, a single off of Francisco Liriano. Castillo appeared in a total of ten Red Sox games, batting 12-for-36 with two home runs and six RBIs.
2015
Castillo started the 2015 season with the Triple-APawtucket Red Sox, where he appeared in 40 games, batting.282 with three home runs and 17 RBIs. He was called up to Boston in the second half of May; he appeared in 80 MLB games for the Red Sox, batting.253 with five home runs and 29 RBIs.
2016
Castillo spent most of the 2016 season with Triple-A Pawtucket; he made only nine appearances with Boston, one in April and eight in June, batting 2-for-8 without a home run or RBI.
Minor leagues
On June 18, 2016, Castillo was put on waivers by the Red Sox; he cleared waivers on June 20 and was outrighted to Pawtucket, where he spent the rest of the season. He appeared in a total of 103 Triple-A games during 2016, batting.263 with two home runs and 34 RBIs. During the 2017 season, Castillo played in 87 games for Triple-A Pawtucket, batting.314 with 15 home runs and 43 RBIs. He did not play any MLB games with Boston, nor was he added to the 40-man roster. Castillo remained with Triple-A Pawtucket for the 2018 season, appearing in 117 games while batting.319 with five home runs and 59 RBIs. For the 2018 season, he was named to the International League All-Star Team, and his.319 average led the International League. After being a non-roster invitee to Boston's 2019 spring training, Castillo started the 2019 season as the oldest player on Pawtucket's roster. With the 2019 PawSox, Castillo appeared in 120 games, batting.278 with 17 home runs and 64 RBIs. After the 2019 season, Castillo did not exercise an opt-out clause in his contract, thus remaining in Boston's minor league system for 2020, the final season of his seven-year contract with the Red Sox. In 2020, he was again a non-roster invitee to Boston's spring training.
Personal life
Castillo is married, and has one daughter. In early 2018, he was able to return to Cuba for the first time since his defection. As of the 2018 season, Castillo continues to live in Boston and commutes to home games played in Pawtucket, Rhode Island, about a one-hour drive. In April 2019, he put up for sale a home he owns in Pinecrest, Florida, with an asking price of $3,953,000.
