Troy O'Leary, an American professional baseball player, spent a decade in Major League Baseball (MLB) primarily as an outfielder. Born on August 4, 1969, in Compton, California, O'Leary attended the University of Arkansas at Pine Bluff before being drafted by the Milwaukee Brewers in the 13th round of the 1987 MLB Draft. He made his MLB debut with the Brewers on May 9, 1993.
O'Leary's tenure with the Brewers was relatively short. After playing parts of two seasons with Milwaukee, he was claimed off waivers by the Boston Red Sox in April 1995. This move marked the beginning of his most productive years in the major leagues. With the Red Sox, O'Leary became a regular in the outfield, known for his left-handed batting and solid defensive skills.
During his time with Boston, O'Leary developed a reputation as a reliable hitter. In 1996, he hit .308 with 15 home runs and 72 RBIs, establishing himself as a key player in the Red Sox lineup. His performance in the 1999 season was particularly noteworthy, as he hit .280 with 28 home runs and 103 RBIs, helping the Red Sox secure a playoff berth. One of his most memorable moments came during the 1999 American League Division Series (ALDS) against the Cleveland Indians. In Game 5, O'Leary hit two home runs, including a grand slam, leading the Red Sox to a decisive victory and advancing them to the American League Championship Series (ALCS).
O'Leary continued to be a steady presence for the Red Sox until 2001. After his time in Boston, he signed with the Montreal Expos for the 2002 season. His stint with the Expos was brief, and he finished the season with the Chicago Cubs. In 2003, O'Leary played his final MLB season with the Cubs, appearing in 68 games.
Throughout his career, O'Leary was known for his ability to perform in clutch situations and his consistent offensive production.
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