That doesn't seem like a good excuse to give him $25 million.
The fact is, a good GM know when to fold them. Just because Rollins was the best option at that point in time doesn't mean you need to go out and give him a 3 year/$33 million deal.
Saying he made those moves just to continue to make the playoffs is completely correct, actually. Like you said, try to name a starting pitcher on that 2008 WS roster, outside of Hamels (and Moyer, Blanton, Kendrick, etc.). It was rough. Without the addition of starting pitching, the team could easily have either missed the playoffs (more likely in 2010 than 2009), or been bounced earlier.
The goal of a GM is to make sure to win as soon as possible, as often as possible, without being saddled with overpaid veterans. Who should he have moved? I wouldn't have signed Ryan Howard to that contract, even then. I would not have brought back Rollins. Would it hurt for a season or two? Yes, probably. But right now we wouldn't be talking about the age and declining talent of the Phillies, but a possible youth movement along side of veterans like Utley, Hamels, Lee, and Halladay. Draft smart, sign smart.