Boston Red Sox pitcher Tim Wakefield is finally retiring at the grand old age of 45. Wakefield played his first two seasons as a member of the Pirates -- he made his debut with Pittsburgh in 1992, when he was already 25 (!), and pitched two complete games in the 1992 ALCS, winning them both. Then his fortunes declined as the Pirates' did -- he struggled in the 1993 and 1994 seasons, striking out fewer batters than he walked in the majors in 1993 and in the minors in 1994.
↵The Pirates released Wakefield early in the 1995 season and haven't had a winning season since '92 -- Wakefield's retirement may shut the book on active players who have played for a winning Pirates team. (Miguel Batista pitched two innings on that team and is currently with the Mets; it's not yet clear whether he'll play this year or not, but he isn't listed on the Mets' depth chart.)
↵Things turned out much better for Wakefield than they did for the Bucs. Wakefield caught on with the Red Sox, where he pitched for 17 years (!!), becoming the premier knuckleball pitcher of his generation. (That's quite a 'whoops' on the Pirates' part.) Wakefield won an even 200 games over the course of his career. He was never a dominant pitcher, but he was usually above average, and it was always fun to watch him, because his style was so incredibly different from most pitchers of his era.
↵For more on the Red Sox, check out Over The Monster.