Much like Wade Boggs 20 years earlier, Hillenbrand was stuck in Boston’s minor league system and didn’t get his first chance in the majors until he was 25 years old. A third baseman, Hillenbrand showed he could hit in the farm system, but was a mediocre defender at the hot corner. As a rookie in 2001 he was the Sox regular third baseman, showing decent promise while performing inconsistently. He improved in his sophomore season, belting out 43 doubles and 18 homers while making the All-Star team. But in 2003 the bloom came off the rose for Hillenbrand in Boston. Newly acquired veteran Bill Mueller ate into Shea’s playing time at third, and even though Hillenbrand was hitting .300, it was difficult for manager Grady Little not to play Mueller when he was hitting .380 over the first three months. Hillenbrand sulked and the front office took note. When the Diamondbacks offered relief pitcher Byung-Hyun Kim, Boston GM Theo Epstein jumped at the deal. Stung by his exile from a pennant-contending team, Hillenbrand lashed out at Epstein before leaving town. When Mueller went on to win the batting title, it not only justified the deal, it made Red Sox Nation forget about Hillenbrand.
In Arizona Hillenbrand was thrown into a boiling pot of drama, as the club that had advanced to the World Series in 2001 was now gutted and aging. They lost 111 games in 2004 while Hillenbrand griped about being moved across the diamond from third to first. Even though he hit .310 and led the team in RBI, he was traded to the Toronto Blue Jays after that season for next to nothing. In Toronto things got really bizarre with Hillenbrand. He almost immediately had trouble getting along with manager John Gibbons, a tough disciplinarian. Hillenbrand felt that since he was one of the senior players on the club he deserved a regular starting spot. Instead, Gibbons used Hillenbrand at first, third, and DH almost equally. Still, a disconcerted Hillenbrand made the All-Star team in his first season as a Blue Jay. In ’06 Hillenbrand and his wife adopted a baby. After returning to the team after being away a few days to secure the adoption, Hillenbrand stewed when he found that the organization didn’t congratulate him on it. He felt slighted that the big family event wasn’t celebrated by his teammates, or at least acknowledged. When he returned he refused to sit next to his teammates on the bench and he wrote some disparaging remarks on a whiteboard in the clubhouse, like “Play for yourself.” and “This is a sinking ship.” Gibbons confronted his player and the team designated him for assignment that day. When several teams expressed interest in him, the Jays traded Hillenbrand to the San Francisco Giants.
Shea played out ’06 with the Giants, declared his free agency and signed with the Los Angeles Angels. But he wore out his welcome with the Halos when he stated publicly in July: “If I’m not going to play here, give me enough respect to trade me or get rid of me.” The Angels obliged, releasing him. The rest of his career was spent in the minor leagues, in a brief spell with the Los Angeles Dodgers, and desperately trying to get back into good graces with a major league club.