He slowly moved up the minor league ladder and finally in 1993, after a decent year at AAA, he was given the opportunity with the Brewers, 7 years after he was drafted. In fact, he wasn't even on the Brewers prospect radar until 1992 when he won the Texas League batting title with a .334 average. So on May 9th,1993, O'Leary made his major league debut against, ironically, his long-time future team, as a defensive replacement for Greg Vaughn in a 6-0 win.
The sweet-swinging lefty outfielder batted .293 in his 41 at bats with the Brewers and he got another look in 1994 with the Brewers. He was evidently unimpressive to the Brew Crew and found himself being picked up by the Red Sox on waivers the following season, once the dust from the strike had settled. It was a good fit in Boston and he spent the next 7 seasons playing LF and RF for the Red Sox, starting and hitting mainly against right-handed pitchers.
He put up good numbers in Boston, hitting 10 or more homers in all 7 seasons and reached the 80 rbi mark 4x. He drove in 103 in 1999. If you look at O'Leary's scouting scores, you'll notice that he always hovered slightly above average for all statistical categories compared to his peers and he thus became known as a "professional hitter". O'Leary's biggest moment as a Red Sox came in October of 1999 when he hit an important grand slam against Cleveland in game 5 of the ALDS which brought the Sox back from 3 runs down and propelled them to victory and a trip to the ALCS.
O'Leary played a season each with the Montreal Expos and the Chicago Cubs before playing a season in Korea in 1994.
When it was all done, O'Leary had played 1200 games, had 1100 hits, 127 homers, a .274 career average and a 780 OPS. He made it to the playoffs in 3 different seasons but never managed a World Series appearance. He batted .217 in the post-season.
A Red Sox blog named O'Leary #65 on its all-time list of greatest Red Sox, in large part due to his 1999 grand-slam.
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