A Red Sox lifer, Greenwell was the left field heir to Ted Williams, Carl Yastrzemski, and Jim Rice. His first three major-league hits were home runs, the first a 13th-inning game-winner at Toronto on September 25, 1985. With a smooth lefthanded batting stroke modeled after George Brett‘s, he finished third in the 1987 AL Rookie of the Year voting behind Mark McGwire and Kevin Seitzer. The next year he beat out Rice for the left field job and garnered MVP consideration when he led Boston to a division title, hitting .325 with 22 HR, 119 RBIs and only 38 strikeouts.
Greenwell was an All Star in 1988 and 1989, and could still be counted on to bat around .300 even as his power numbers began to tail off afterwards. He hit .297 with 14 round trippers in 1990, but suffered through an 0-14 ALCS as Boston was swept in four games by Oakland. In 1992, a knee injury limited him to just 49 games, but he came back strong the following season, hitting .315 with 72 RBIs. He knocked 15 home runs while batting .297 in 1995, his last full season, helping the Red Sox to their fourth AL East title in his tenure with the club.