It's fitting that Tim Wakefield would get back to Pittsburgh for the first time since 1993, as he was sentenced to the minors in 1994 and cut loose by the team in 1995, as he approaches the 200 career win mark. Pittsburgh is where he got his start in 1992 as a 25-year-old knuckleballer. It's where he was drafted back in 1988, in the eighth round of the amateur entry draft. He played first, second, and third base back then, but he couldn't hit at all, so he became a pitcher. That was 2,914 innings, 574 games pitched, 415 games started, and 183 wins ago (and let's not forget the 22 saves, either).
Wakefield has been to the playoffs nine times and won two World Series in his 17 seasons with Boston, while the Pirates have not even finished with a record of .500 or better during the same stretch. Wakefield is, as Tim Britton mentioned earlier today, the last player in the major leagues to ever wear a Pittsburgh Pirates uniform for a winning Pirates team. That very well may change after this season -- Wakefield could retire, or the Pirates may finish at .500 or better for the first time since 1992 thanks to some quality defensive play.
Thanks to Clay Buchholz's stint on the disabled list and Daisuke Matsuzaka's inability to get through another season in one piece, Wakefield has had multiple chances to pile up wins. Now, wins are no great indicator of ability or even of success, but each win for Wakefield has to feel special, and there is something satisfying about his approach of 200 of them. Yes, it's a shiny and round number, and having 200 wins won't make Wakefield any better than if he had 199 of them, but this is a pitcher who was released all those years ago by the organization that has since set the record for being more below-average than any other team in the history of professional sports. Granted, maybe his release, while in no way as significant as losing Barry Bonds to free agency, was just part of the organization's problem in regards to failing to identify talent that could help them, an issue that has plagued them for the better part of two decades. Doing well in 1995 must have felt great for Wakefield, as he didn't pitch in the majors in 1994 and had been released, but to still be here, succeeding, and with 10 seasons over .500 on his resume compared to the Pirates zero since he was sent packing, has to feel amazing, even if that feeling lives somewhere deep inside his subconsciousness.
This isn't to say that Wakefield is out for some kind of Freudian revenge all these years later, but that it has to feel... nice. He's still around, he's still pitching well, and now he gets a chance to not win #198 for his career (and #184 since coming to Boston) against the organization that let him loose, in the city he got his start in all those years ago. In his one career start against the team, which took place at Fenway, Wakefield went seven innings and struck out five while allowing no runs, but took home a no decision. Thanks to Boston picking him up, he has never lost to Pittsburgh, and this close to 200 wins (and just a few notches of the belt away from the Red Sox franchise record), now is not the time for him to take his first loss, either. He can't will himself to a victory, of course, but if you've never outright rooted for Wakefield to win before, these next few starts, starting with this weekend's, would be a good time to do so.