Yeah, I don't really like the idea of giving years to people in their 30s unless they're like Curt Schilling or Greg Maddux or something. I'd honestly prefer not to go with a 4 year deal on someone who's 32. I told you, I thought Lackey was like 2 years younger than he is though, I still didn't like giving 5 years to him.
The money isn't the issue, I think the Sox sort of had to overpay because he was the top pitcher on the market, and considering how quickly the cost of pitchers is going up, they gave him a deal that they maybe shouldn't have for years and for a couple million per year too much. After year one of the deal I thought he could live up to it all things considered, but instead he started to play like he did at the beginning of 2010, and never regained control.