While a member of the Red Sox, Baylor delivered a key hit in the 1986 American League Championship Series when he hit a two-run home run with one out in the top of the ninth inning during game five against the California Angels. At the time, the Angels led the series three games to one and were one out away from their first ALCS victory. The Red Sox went on to win the game and eventually the ALCS, denying the Angels their first trip to the World Series. Al Michaels, broadcasting the game for ABC, called it the greatest baseball game he had ever seen.
Baylor reached the World Series three times in his career, in consecutive years with three different teams. Baylor played in the World Series with the Red Sox in 1986, the Twins in 1987, and the A's in 1988, and he was on the winning side in 1987. Baylor is one of two players in history to accomplish this feat; Eric Hinske is the other. Baylor was a power hitter known for crowding the plate. He set the Red Sox team record for most hit by pitches in a season (35 in 1986); in his career, he was hit by pitches 267 times, fourth-most all time. Baylor retired with 285 stolen bases, 2,135 hits, and 338 home runs.