Troy O’Leary had posted several good seasons for the Red Sox in the late 1990s.
By the time the Cubs signed him as a free agent before the 2003 season, he was a bit player expected to give the Cubs’ regular outfielders some rest from time to time, and to serve as a pinch-hitter.
You probably don’t remember him much, because O’Leary hit just .218/.275/.356 in 194 plate appearances with five home runs.
One of those home runs was memorable. On September 6 the Cubs were in Milwaukee playing the Brewers, riding a four-game winning streak. O’Leary had already gone 1-for-2 with a walk and an RBI on a sacrifice fly when he came up in the ninth inning with two out and two runners on. The Cubs were clinging to a 5-4 lead.
O’Leary hit a three-run homer to give the Cubs a cushion going into the bottom of the ninth, and Mike Remlinger retired the side in order for an 8-4 win. The Cubs went into first place with a win over Milwaukee the next day. They would briefly fall out of first place later in the month, but a last-week rally and collapse by the Astros made them N.L. Central champions.
O’Leary’s final at-bat in the major leagues was in Game 7 of the NLCS as a pinch-hitter. He homered off Josh Beckett to make the score 9-6, but as you know, that’s as close as that game got in the late innings. He continued his career in Korea in 2004, hitting .265/.346/.493 with 10 home runs in 63 games for the Samsung Lions.