Henderson is best remembered for the two-out, two-strike home run he hit in the top of the ninth inning in Game 5 of the 1986 American League Championship Series. He helped his teams reach the World Series four times during his career—Boston in 1986 and Oakland from 1988 to 1990, with Oakland winning the championship in 1989. His uncle Joe Henderson appeared in 16 MLB games as a pitcher during the mid-1970s.