Red Sox “Way Back Weekly” – Troy O’Leary


With the offseason officially underway, we here at BSI have started a new segment called “Way Back Weekly,” taking trips down memory lane to highlight specific players or teams and also check in on what they’re doing today. Here is part two of “Way Back Weekly.”

Former Red Sox outfielder Troy O’Leary spent seven of his 11 major league seasons in a Boston uniform, and certainly had his most success while calling Fenway Park his home.

When O’Leary’s name is mentioned, two legendary swings of the bat during the 1999 ALDS in Cleveland may immediately jump to mind. While this game is certainly worthy of consideration for the lefty’s big baseball moment, he shouldn’t be overlooked for the little things he contributed during his tenure from 1995-2001.

Never a great player, never an all-star, and never showing up on any major offensive category leader boards, O’Leary was a force in the lineup during the late 1990s. He helped the squad reached the division series in 1998 and then one step further the next season. O’Leary’s infectious smile, open batting stance (with a hint of lefty Gary Sheffield bat movement), and his seemingly positive effect on the clubhouse are what I remember most.


  • The California native was drafted by the Milwaukee Brewers in the 13th round of the 1987 amateur draft.
  • O’Leary made his major league debut on May 9, 1993 with the Brewers (ironically against the Sox.) He entered as a defensive replacement for the powerful Greg Vaughn in the eighth inning but did not get an at-bat.
  • After receiving sparse playing time with the Brewers, O’Leary was claimed off waivers by the Sox on April 14, 1995.
  • Gradual improvement over his first four seasons with the Red Sox culminated in his best season of his career in 1999. O’Leary hit .280 with a team-leading 28 home runs and placed second on the team with his 103 runs batted in.
  • At first, O’Leary’s regular season success did not carry over to the playoffs that year. However, after a rough beginning to the ALDS vs. the Indians, O’Leary carried the offense in game five, hitting two home runs and driving in seven runs. O’Leary’s legendary performance at the dish during the do-or-die game is often overshadowed by the equally legendary performance of Pedro Martinez (pitching out of relief.)
  • O’Leary spent the 2002 season with the now defunct Montreal Expos and played the 2003 season with the Chicago Cubs.
  • He played in his final game on Sept. 28, 2003, picking up two hits.


  • According to the Boston Globe’s Nick Cafardo in 2009, O’Leary has been thoroughly enjoying retirement (time with family, playing golf.)
  • Cafardo also notes that as of 2009, O’Leary had made his way back to the west coast, residing in the Phoenix area where he iss coaching baseball.
  • Hey look, even the likes of Troy O’Leary has his own Facebook page! It has racked up a hefty 347 likes!