Baseball teams come to be defined by their players as much as the successes or failures they have with their win/loss records. In particular, the Boston Red Sox have a rich tradition of players who have left indelible marks on the franchise and its fans. One player who is surely in that category is Troy O’Leary, who came to Boston under humble circumstances, but left as a tremendous success.
The left-handed O’Leary was a 13th-round draft choice of the Milwaukee Brewers in 1987. He was a .300 hitter in the minors, but could never crack the team’s big league roster beyond brief stints in 1993 and 1994.
Shortly after the start of the 1995 season, O’Leary was released, but was quickly snapped up by the Red Sox, who had a big hole in right field. It turned out to be a brilliant maneuver, as he went on to hit .308 with 10 home runs and 49 RBI in 112 games, and the Red Sox won the American League East.
O’Leary wound up having a productive seven-year career with the Red Sox, playing both right field and left. His best season came in 1999, when he hit .280 with 28 home runs and 103 RBI in 157 games.
His defining moment came that same year in the ALDS in the deciding Game 5 against the Cleveland Indians. Behind his two home runs (including a grand slam) and seven RBI, the Red Sox rallied from an early deficit to take the series and advance to the ALCS against the New York Yankees.
While they team failed to make the World Series in 1999, the heroics of O’Leary became a permanent part of Red Sox lore.
His final season in Boston came in 2001 when he appeared in 104 games, but hit just .240 with 13 home runs and 50 RBI.
Following the season, he signed as a free agent with the Montreal Expos. After one season there, he finished his major league career with the Chicago Cubs in 2003. He also played in Korea in 2004, and in Mexico in 2005 before calling it a career.
During his 11 seasons in the majors, he hit a combined .274 with 127 home runs and 591 RBI. He was often overshadowed in Boston by bigger names like Nomar Garciaparra, Pedro Martinez and Mo Vaughn, but the once lightly-regarded player carved out a very nice career and niche for himself in team history.
Other than trying to jumpstart a baseball reality show, O’Leary has remained out of the spotlight in retirement. But that shouldn’t come as a surprise, given the way he quietly became one of the most consistent players in Red Sox history.
I had the opportunity to exchange messages with O’Leary and ask him a few questions about his career. Check out what he had to say!
Troy O’Leary Questionnaire:
Who was your favorite coach or manager?: Kevin Kennedy.
What was the strangest thing you ever saw as a player?: A routine ground ball and a person ran on the field naked.
Who was the toughest pitcher you ever faced?: Randy Johnson.
If you could do anything differently about your career, what would that be?: Not go to Korea.
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