Roy Halladay was at a crossroads in his career and with the Philadelphia Phillies. After two injury-plagued seasons, the Phillies would have to choose whether to keep Halladay for one more run -- like they're keeping all their other aging stars -- or let him start over elsewhere. Yet Halladay took a different path on Dec. 9, as he retired from baseball altogether.
Instead of retiring with the Phillies, however, Halladay signed a one-day contract to retire with the Toronto Blue Jays. While Halladay got his biggest fame with Philadelphia -- along with a perfect game and a postseason no-hitter in 2010 -- Toronto launched his career and first made him a Cy Young level ace.
Such success is why the Phillies let him anchor a super rotation in 2010 and 2011. Yet the sad irony is that while Philadelphia won a World Series with only one ace in Cole Hamels in 2008, it won none after that with several aces. Halladay did his part, but was outpitched in the 2010 NLCS and in Game 5 of the 2011 NLDS as well.
After that, everything went downhill for Halladay and the Phillies, due to injury and age. His arm seemed to break down right before Philadelphia's eyes, leaving his future uncertain after his 2012 comeback fell short. Nevertheless, the assumption was that if the Phillies didn't keep him, Halladay would sign with another team.
In all major sports, former legends keep hanging on even after getting hurt and going past their prime. Halladay didn't retire at his prime, but he left before he could do more damage to his arm and legacy. The Phillies already saw Steve Carlton fail to do that in the mid-1980s, as he bounced around with several teams before finally retiring in his 40s.
On the other end of the spectrum, Halladay is cutting his losses now at age 36, leaving behind a career with 203 wins and two Cy Youngs. But he missed out on a world championship and only had two real chances to get it with the Phillies. That will be left up to the Hall of Fame to factor in or not once Halladay is eligible for voting.
Meanwhile, the Phillies are left with Hamels and Cliff Lee to lead their rotation, as they look for the final burst of glory that Halladay couldn't put together.