The big problem with Ruben's regime that they didn't win another WS or two. If Damon doesn't steal third and Hamels doesn't implode....they're going back to back and that would change a lot of opinions on Rube. Hell, if Cody Ross isn't Babe Ruth and Cliff Lee doesn't blow a four run lead against STL....they might have been in 4 straight WS. More championships and everyone doesn't have a problem with the way he's run things. That being said, his biggest problem was the idea that he continually overpaid to try and right mistakes that he made.....Think about it......
1) Not locking Werth up in 08. Werth started 08 platooning with Jenkins. By the end, it was obvious that Werth was pretty good. He's 29 at that time and wasn't making anything. Amaro went into 09 with him as the starting RF. A GM with foresight tears up his current contract and locks him in until he's about 34/35. The Phils had no problem paying Pence 10+M in 2012. You think that they could have gotten Werth for less than that after the WS in 08? I do. Having Werth elminates the need for Pence, thus the Phils would have kept the prospects that they required to get Pence.
2) He gets Lee in 09 (great trade).....and then gets Halladay in 10 (another great trade), then decides he's spending too much on pitching so moves Lee(horrible trade). Halfway thru 10, he decides he's needs more pitching and gets Oswalt (mixed trade....Oswalt pitched well)..yet he pays Oswalt just about as much as he would have had to pay Lee. So he essentially gave up three prospects (Happ, Villar, Gose) AND a top of the rotation pitcher in the first half of 2010 for Oswalt's second half and Aumont, Gilles and Rameriez. Neverminding that he's on the hook for Oswalt's contract in 2011.....which plays into:
3) He finally decides he wants Lee again...so he resigns him (great move). Now he has 4 aces.....but noone to play the OF. So he moves a cache of players for Pence......when it might have been simpler to run Lee, Hamels, Halladay, Kendrick, Worley and Happ out there....and use more of the Oswalt money to pay Werth whom he would have locked up in 08....
So by locking up Werth in 08 and not trading Lee in 09....he would have had Werth in 2011,2012,2013....Lee in 2010 and Gose, Villar, Happ, Singleton, Cosart and Santana to play with and grow......all for about the same amount of money that he ran thru with Oswalt and Pence.