Hillenbrand played 72 games in 1996 for the Low-A Lowell Spinners in the New York–Penn League. In 1997, he was promoted to the Sarasota Red Sox of the Florida State League, and was promoted again after 57 games, finishing the season with 64 games with the Michigan Battle Cats of the Midwest League. Despite being drafted as a shortstop, he played at first base and third base his first two years in the minors.\n', '

In 1998, still with Michigan, he was converted to play catcher and responded with his best season in the minors, with a .349 batting average and 19 home runs. This earned him a promotion in 1999 to AA Trenton Thunder of the Eastern League. However, a leg injury restricted him to only 69 games.\n', '

The 2000 season saw Hillenbrand back at Trenton, now back to playing first base and third base as the injury prevented him from catching. An average season at age 25 did not bode well for his chances as a prospect, but he parlayed an invitation to spring training with the Red Sox in 2001 into a spot on the big-league team for opening day. Hillenbrand played 139 games for the Sox in his rookie season, mostly at third base, but a .263 batting average failed to hide his failure to hit with power and reach base adequately (he had one of the lowest walks-to-plate appearances rates in MLB). In 2001, he had the lowest range factor among all AL third basemen (2.46).\n', '

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