Now, the context in which I'm contemplating this is that I'm currently seeing Oswalt getting lit up in the NLDS but, odd context aside, I think Oswalt is exactly what the Red Sox need in 2012. First of all, lest anyone complain, let me clarify that Oswalt is not technically a free agent, and we won't technically know if he is until after the World Series; the Phillies hold a $16 million option for him with a $2 million buyout- given, however, the great success of Vance Worley, the limited innings that Oswalt pitched this year, and the increasing cost of guys like Cole Hamels (who they're more likely to want to sign to a long-term deal) and Hunter Pence, it seems terribly unlikely to me that they will. So lets proceed as if he will be a free agent.
He had also, earlier this year, when he hurt his back as a result of helping his family clean up after being hit by a hurricane, he had said he might retire after the season, but he has since recanted that.
Let me go through some quick bullet points on why the Red Sox should sign Oswalt:
1. He's quite good. In 139 innings this year, he posted a 3.69/3.44/3.95 ERA/FIP/xFIP slash line. This was a down year for him.
2. He's a free agent who will be signable on a 1-2 year deal, depending on how much longer he wants to pitch.
3. He's not CJ Wilson. I have nothing against CJ, but I do have something against giving a long term contract to a lefty who has only started for a couple of years.
4. He's also not John Lackey. This is in no way related to Oswalt, really, but everyone who is not John Lackey should be appreciated. If, for example, I were asked to describe something positive about Bill Hall, it would be that he is not John Lackey.
5. Personality-wise, he might be the opposite of John Lackey. He quietly goes about his business, yet is liked by his teammates. Like a sort of pitching J.D. Drew. He won't be a vocal leader, but he'll be a leader by example, doing what he needs to do.
6. He pitches a lot of innings. We need this.
Now, the possible knocks against him are his age (just turned 34) and the injury this year. I don't personally view the injury as a huge deal, as it was suffered outside of baseball, and because he has been generally quite durable through his career. This, combined with his age, present some warning signs, but if you're looking to sign a free agent for a short deal, you're not going to get an absolutely perfect player.
As far as a deal, the most comparable one I can think of is the 2 year extension 36-year old Chris Carpenter signed with the Cardinals for $21 million. Oswalt is a bit younger, but also has not pitched quite as many innings as Carpenter has the last few years, and I'm imagining a deal would be somewhere in that ballpark.
As we're all well aware, the Red Sox may not have a ton of payroll room available this year, but to get a good pitcher without committing a ton of years and dollars, Oswalt is probably the best option out there. I think that, whether through insurance on Matsuzaka, trading, or just finding the room, Oswalt will provide better value to the Sox than most any other option on the free agent market in their greatest area of need for 2012.