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The Red Sox acquired Henderson during the 1986 pennant drive. He hit a two-out, two-run homer for Boston in the top of the ninth inning of Game Five of the 1986 LCS with the California Angels one strike away from their first World Series appearance. The game was won on Henderson's sacrifice fly in the 11th inning and also featured a home run by Bobby Grich that popped out of Henderson's glove and over the outfield wall.

Traded to the Giants on September 1, 1987 to make room for rookie Ellis Burks, Henderson helped the Giants to a division title and then signed as a free agent with Oakland that winter. The centerfielder posted career-high totals of 24 homers, 38 doubles, 100 runs, 94 RBI, and a .304 batting average, (51 points above his previous career average) for the AL champion 1988 A's. In the 1989 WS, he hit home runs in consecutive innings in Game Three after just missing one in the first inning (a double off the railing).

Henderson was the Mariners' first pick in the 1977 free-agent draft. At the time of his trade to Boston, Henderson was Seattle's career leader in home runs and was tied for the team lead in extra-base hits. He is the nephew of Joe Henderson, a pitcher with the White Sox and Reds in the 1970s. (TF)