At first glance, this is a terrible deal for the Phillies. They're already locked into monster contracts for a large pile of other guys. There are younger players coming up on free agency - Shane Victorino, Hunter Pence - who are going to need to be either paid or replaced, and there's not a lot coming up in the system. Then there are the guys who are just going to need to be replaced, and one gets the feeling the Ty Wiggingtons of the world aren't going to be the preferred option next go-round. And of course, there's luxury tax, all of which add up to say that the Phillies spent money they didn't have to reinforce an area they didn't need to, and screwed themselves in the process.
Except, of course, it's never that simple. You can, as they say, never have too much starting pitching, and Hamels' deal isn't out of line for what you pay for an ace. And yes, he is an ace - durable, often better than his W-L record, and usually capable of going deep enough into games to hide the Phillies' dreadful bullpen. As for the money, to be blunt, the Phillies can afford it. They are in one of the largest single-team markets in the US. They sell out every night. They are going to, in a few years, get a new local television rights package that, if it is in line with the ones being signed in places like Anaheim, will pay for the Hamels contract and a few metric tons of scrapple besides.
And, to be blunt, there are two things that keep that stadium filled: winning and stars. Hamels is a star, a guy who came up through the farm system and has never played for another team. He puts butts in seats and moves jerseys in the gift shop and, despite bearing an uncanny resemblance to one of the two brothers on Supernatural, is well-liked by the fan base. And nobody out there is going to say that having six more years of Cole Hamels is going to hurt the Phillies' chances of winning. Yes, you can say that spending the money they spent on Hamels on a viable center fielder or third baseman would go that route, but to be blunt, there aren't any impact bats out there to spend that money on. Better to double down on pitching, pray that they get something out of Dom Brown and Freddy Galvis, and rebuild the bullpen on the cheap instead.
Maybe they should have signed him sooner. Maybe they could have gotten him for less. But as far a bajillion dollar contracts for pitchers go, this one ain't bad.