Greenwell was born in Louisville, Kentucky. When he was five years old, his family relocated to Fort Myers, Florida; he would later attend North Fort Myers High School, where he played both baseball and football.\n', '

Greenwell was drafted in the third round of the 1982 Major League Baseball Draft by the Red Sox, and was signed on June 9, 1982. Throughout his Red Sox career, Greenwell suffered under the weight of lofty expectations for a Boston left fielder, as since 1940 the position had been occupied by Ted Williams, Carl Yastrzemski and Jim Rice – all MVP winners, regular triple crown candidates, and eventual members of the Baseball Hall of Fame. Although his play rarely reached the level of his predecessors, he provided a solid and reliable presence in the team\'s lineup for several seasons. Well respected, he also served as the team\'s player representative for a time. Greenwell was runner-up for the 1988 American League MVP Award to Jose Canseco of the Oakland Athletics; years later, Canseco\'s admission of steroid use led Greenwell to ask, "Where\'s my MVP?"\n', '

On September 14, 1988, Greenwell hit for the cycle, becoming the 17th player to do so in Red Sox franchise history. On September 2, 1996, the Red Sox beat the Seattle Mariners 9–8 in 10 innings at the Kingdome, with Greenwell driving in all nine runs for the Sox, a record for most runs driven in by one player accounting for all of that team\'s runs in a single game. He also holds the American League record for most game-winning RBIs in a single season, with 23 in 1988; the game-winning RBI has since been discontinued as an official statistic. Greenwell was inducted to the Boston Red Sox Hall of Fame in 2008.\n', '

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