Career

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 had batted over .330 twice before. He was promoted to Milwaukee a year later, and after two seasons, he was selected off waivers by the Red Sox.

O'Leary hit his first career home run September 1, 1994 off San Diego Padres reliever Adam Clark.

From 1996-1998, he collected at least 80 RBI in each season, batting .308 in 1995 and a career-high .309 in 1997.

Troy enjoyed the best year of his career statistically in 1999. He led the team with 28 home runs in the regular season, was second on the team to Nomar Garciaparra in RBI (103), and finished with a .280 batting average. He played in 157 of the 162 regular season games and finished with 596 at bats, leading the team in both categories. Troy also posted 84 runs (3rd on team), 167 hits (3rd on team), 36 doubles (4th on team), and a .495 slugging percentage (3rd on team).

The greatest moment of O'Leary's Major League career took place on October 11, 1999, in the deciding game 5 of the ALDS versus the Cleveland Indians. Boston was trailing 5-2 going into the top of the third inning. With runners on second and third, Indians starter Charles Nagy chose to intentionally walk Nomar Garciaparra, who had homered in the first inning, to load the bases for O'Leary. O'Leary responded by sending the ball over the right field fence for the first grand slam in Red Sox post-season history. When the seventh inning began, the game was tied 8-8. The Indians again, chose to intentionally walk Garciaparra to get to O'Leary, this time with Paul Shuey on the mound. O'Leary responded with a very similar swing to his grand slam in the 3rd inning, hitting a line drive over the right field fence for a 3 run home-run to help seal the victory and advance to the ALCS against the New York Yankees.

[ Source: Wikipedia ]