Alright, this one might be a little less obscure. Or maybe not, depending on our age.
Long before Tim Wakefield was setting records and winning World Series as a successful starter and clutch playoff performer for the Red Sox he was...a successful starter and clutch playoff performer for the Pirates.
...who them promptly released him. Queue history.
I think there have been enough ESPN special features, Outside the Lines pieces, and Sportscenter clips on the Sox/Yanks dominated ESPN that most of us know the story of Wake.
Minor league flameout attempts to salvage career via knuckleball. Rookie sensation. Disaster the next year. Red Sox legend.
But the Pirates were also entering what has turned out to be two decades of losing baseball. And Wake wasn't exactly holding back any significant minor leaguer stars by staying on the roster. To flat out release a player who had had significant success in the majors seems foolish at best.
And maybe that's the bigger theme here. The issue isn't that players like Wakefield or Jose Bautista have gone on to have impressive careers elsewhere. Someone always gets away. Brian Giles and Jason Bay worked out the opposite way, and I can assure you Pirates fans are not complaining about that.
The larger issue is giving away potentially valuable assets for little to no return. Bautista and Wake were both players on glaringly slow developmental paths - Bautista's career was derailed by being a Rule 5 pick (which never should have happened in the first place,since the Bucs had 40 man spots open during the Rule 5, lost him, only to trade for him later in the season), and knuckle ballers are typically slow to develop. The teams these players were jettisoned from were, simply put, bad. Leaving a questionable player on a roster spot would not hurt, if it means losing Chris Duffy or Rick White.
But what's done is done. Instead, we get to both appreciate the time he did spend in Pittsburgh, and be regularly reminded by ever ESPN clip showing him giving up a barrage of homers in black and gold, before cutting to a sequence of him baffling Yankees hitters at Fenway. Thanks ESPN!