Dan Marino, Brett Favre, and Curt Schilling? While I'm a fan of two of the aforementioned, all three of these legends waited too long to end it. One could arguably add Michael Jordan to the list, as he had such a weak retirement that nobody believed he was done when he retired as a Washington Wizard either.
It's not that Schilling wasn't a dominant force on the mound (especially in the postseason), it's just that when you see that your next birthday will make you a 42-year-old, you should know that it's time to hang it up.
I'm not of the persuasion that Schilling just came back for the money and pulled a fast one on the Red Sox. One, I don't think it's possible to pull a fast one on the front office of the Boston Red Sox —John Henry, Theo Epstein, and Larry Lucchino all do a tremendous job in personnel decisions. Secondly, Curt himself said that if he was coming back for the money, it wouldn't have been in Boston.
With that said, it does make me wonder what the motive was for a return. It was at one time reported that Schilling couldn't shake hands over the winter. Did he and the training staff honestly think that rehab (in lieu of surgery) would have him back after the All-Star break?
The fact of the matter is this: love it or hate it, the guys who retire at the peak of their careers (John Elway for example) are remembered ten to fifteen years down the road as more successful than they might have been (again, love it or hate it) at their sport.
John Elway played from 1983-1998. He won two Super Bowls in the last two years of his career, that's about it. Oh, and he threw a fit to play in Denver (a la Eli Manning). It might have felt right to come back to try at the coveted "three-peat," but Elway knew it was time to shut it down.
Contrast that with my favorite of all time—Brett Favre. Brett Favre won one Super Bowl and three NFL MVPs in his illustrious 17 year campaign as the most likable guy to play quarterback. In that course he set a lot of records, virtually re-writing the record book previously authored by Dan Marino.
Also in that time, he set the record for the most interceptions by a quarterback, took an incalculable beating on his aging frame, and ended his career in Green Bay, throwing a game-deciding, overtime interception in the NFC Championship Game.
Die-hard Packers fans such as myself will remember him for being the gunslinger and the only 3-time NFL MVP, as well as bringing a Super Bowl trophy back to Titletown. But sadly, a lot of people will remember him not for those things, but for being the guy who drug it out too long, chasing a championship for over ten years that wasn't there.
It's not as though by retiring these athletes are forever lost. What it could mean is that they are held in a more endearing way than if they try to "fire it up" for one more year. I couldn't think of a better way for Schilling to go out than with his third World Series ring on his finger, but apparently he saw himself going out with his fourth.