I think that it is clear that Derek Jeter isn't really the player he used to be. So I think it's a smart decision for him to retire after the 2014 season so that he can retire with some dignity. He has also suffered from constant injuries which are probably factors that encouraged his decision to retire.
Yes, Derek Jeter should retire after the 2014 season, because the top players should always retire while they are on top, so that they leave the best legacy possible. Derek Jeter is one of the best players on the Yankees, and he is very talented. He is started to lose his skill level from his peak, so he should resign on top.
As he is already planning to do so, hoping for an alternate ending will not doo much. Derek Jeter is a class player and deserves a class ending, and he will get one if he ends his career at the end of 2014. He has played enough years already in the game of baseball.
Since Derek Jeter has announced that 2014 is his last season, he should retire. He's made the decision that he is ready to leave baseball and move onto other pursuits. Jeter has been at the top of his game for a long, long time. He should move on and let someone else rise to the top.
Derek Jeter is one of the most galvanizing persons in Major League Baseball. The games he is involved in become more about him than the teams much less the sport itself. Baseball is about more than controversy or intrigue - it's about the game itself - and if Derek Jeter would let a game of baseball be about baseball then I'd be alright with him staying.