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Greenwell played for the Red Sox from 1985 to 1996, stepping into a position historically associated with legends such as Ted Williams, and later Jim Rice. Despite the high standards set by these iconic players, Greenwell proved himself as an elite athlete. He was a two-time All-Star and finished as a runner-up in MVP voting in 1988, highlighting his outstanding contributions to the team.
In recognition of his impact and performance, Greenwell was inducted into the Red Sox Hall of Fame in 2008. His batting prowess, along with his dedication and professionalism, made him a fan favorite and a respected figure among teammates.