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Ibanez and Polanco are two guys the Phillies may have invested in for too long
Ruben Amaro will often give out a year too many on contracts for some of his signings, both off the free agent market and re-signing his own players.
Often times, they are aging veterans in decline. Raul Ibanez and Placido Polanco come to mind as candidates in this category. Each received a three-year deal, Ibanez's expiring last year Polanco's possibly expiring following this season, and each seems to no longer be worth the original value of the contract.
In theory, it makes sense for some teams that they would need to dish out maybe a year extra to reel in a free agent. But the Phillies are a different animal; they are a destination for players. Ibanez mentioned he got chills watching this team play. Polanco said he never wanted to leave after his first stint here. Jonathan Papelbon said he wanted to play for the Phillies and told his agent to do whatever he needed to make that happen.
Amaro has all the leverage; why does he need to throw in extra years to deals when the players want to come to him?
As far as re-signing internal players, Joe Blanton comes to mind as a deal that has been criticized, and probably deservedly so. In theory, it was nice to secure an "innings eater" with which the team had been familiar, but there really was no need to do so.
Remember, Philadelphia is a destination for players. For every Joe Blanton, there are 2-3 other Joe Blantons just in each of the other 29 teams' rotations. Should they need to move on, or Blanton not want to return after his arbitration years, the Phillies easily could have replaced him. Or they likely would have found Blanton wanting to return if there was no one better out there.
It is similar to how most of the supporting cast of the Miami Heat took huge pay cuts from their true value to come and join the team two summers ago. To them, that was the destination place to play, and it had the players with which they wanted to play.
That is what Philadelphia has become for the last five years or so, and Amaro seems to be spending as if he is general manager of the New York Mets.