Originally drafted by the Milwaukee Brewers, O'Leary came to Boston via the waiver wire in 1995 and took over the left field job in 1998. "WAAAAAY BAAAACCCCK, grand slam Troy O'Leary," was the famous radio call of Jerry Trupiano during the 1999 ALDS Game 5 in Cleveland, where O'Leary hit two home runs, a three-run shot and a grand slam, in a 12-8 win that put the Sox in the ALCS. O'Leary's best season was in 1999, when he had career highs in homers (28), RBIs (103), and doubles (36). He hit .274 with 127 home runs and drove in 591 over his 11-year career. O'Leary retired after the 2003 season after winding down his career with the Expos and Cubs.
(O'Leary's stats and facts