Troy O’Leary spent the majority of his career with the Red Sox, patrolling the outfield with the team from 1995 to 2001. Almost immediately upon his arrival in Boston in 1995, O’Leary became a valuable contributor in the batting order and put up some excellent numbers.
His first season with the Red Sox resulted in a .308 average with 10 home runs and 49 RBI and from there he only got better. His best season in Boston was 1999 when he hit .280 with 28 home runs and 103 RBI. He was also, along with Pedro Martinez, one of the main reasons the Red Sox reached the ALCS that year.
In the same game that Martinez famously threw six innings of no-hit relief, O’Leary hit a grand slam and a three-run homer in the deciding fifth game of the 1999 ALDS to help the Red Sox eliminate the Cleveland Indians and move on to face the Yankees. Unfortunately, within two years O’Leary was the odd man out in the Red Sox outfield (especially since they signed Manny Ramirez in the winter of 2000).
Still, his excellent hitting combined with his excellent defense (a .984 fielding percentage and only 27 errors committed in Boston) made Troy O’Leary one of the best and most underrated Red Sox of the 1990s.