One of Howard's highlights during his time with the Red Sox occurred on August 27, 1967 when the Chicago White Sox were battling the Red Sox for the pennant. With Ken Berry on third base with one out in the bottom of the ninth inning and the Red Sox leading 4-3, Duane Josephson lined out to Jose Tartabull in right field. Not known for having a strong arm, Tartabull’s throw sailed high and was caught by a leaping Howard who blocked the plate with his left foot as he came down, and swipe tagged Berry ending the game. For Red Sox fans, the play was considered a key event during their "Impossible Dream" season.