Troy O’Leary born August 4, 1969 in Compton Califorina ended up being one of those “brought him in as a utility and ended up starting him” players for the Sox.
O’Leary began his career as a 13th round pick in 1987 and didn’t make his MLB debut till quite a while later in 1993 at the age of 23. He played 19 games for the Brewers batting .293 and followed it up with a .273 performance over 27 games in 1994. Sensing stardom, the Sox picked him up on waivers for the 1995 season, and O’Leary found himself with his first chance at a full season.
While in Boston O’Leary never failed to play more than 100 games, and left Beantown with a .276 average over seven seasons along with four straight seasons of 15 homers or more. His best season came in 1999 where he hit .280 while mashing 28 homers and driving in 103 runs as he ranked as one of the most productive hitters on the team that year. You can see his full stats here!
His greatest moment came in the 1999 ALDS against the Cleveland Indians. Ahead 3-2 in the third inning with two men on the Indians elected to walk Nomar Garciaparra to load the bases for O’Leary. Faced with a challenge the outfielder responded by driving a ball over the right field fence for the first grand slam in Red Sox history. In an 8-8 tie later in the game an eerily similar situation appeared as Garciaparra was once again walked to get to O’Leary who took the same swing and drove the pitch over the fence for his second homer in the game to seal the win for the Sox and send them to the ALCS.
O’Leary spent two more seasons in Boston before moving on to the NL, going to the Expos in 2002 then the Cubs in 2003 before retiring at the age of 33.