Troy O'Leary (born August 4, 1969 in Compton, California) is a former left fielder in Major League Baseball who played with the Milwaukee Brewers (1993-94), Boston Red Sox (1995-2001), Montreal Expos (2002) and Chicago Cubs (2003). He batted and threw left handed.
In an 11-season career, O'Leary posted a .274 batting average with 127 home runs and 591 RBI in 1198 games.
A 13th-round pick in 1987, O'Leary enjoyed a great 1992 season at Double-A El Paso, winning the Texas League batting title with a .334 average and stealing 28 bases. O'Leary batted over .330 twice before. He was promoted to Milwaukee a year later, and after two seasons, he was selected from waivers by the Red Sox.
In Boston, O'Leary played a solid right field during three seasons and later switched to left. From 1996-1998, he collected at least 80 RBI in each season, batting .308 in 1995 and a career-high .309 in 1997. His most productive season came in 1998, when he compiled career highs in home runs (28), RBI (103), runs (95), doubles (36), and finished with a .280 average.
O'Leary's greatest baseball moment occurred on October 11, 1999, in the deciding Game 5 of the American League Divisional Series against the Cleveland Indians. O'Leary hit 2 home runs, a 3-run shot and a grand slam, both of which came directly after intentional walks to Nomar Garciaparra. These hits combined with Pedro Martinez to defeat the Indians 12-8 and move on to the American League Championship Series against the New York Yankees.
In 2001, the signing of free agent Manny RamÃrez made O'Leary expendable. After that, he played two years for the Expos and Cubs, retiring from MLB after the 2003 season. He later played in baseball leagues in South Korea, but is now retired.
O'Leary's nickname among his Boston teammates was "Yummy," in honor of his love for sweets.