[Update 3:08 pm] Jim Bowden reports the Red Sox have made an offer to Edwin Jackson, and "prefer him over Roy Oswalt." Read the latest on Oswalt courtesy of Ben Buchanan here.
Free agent starting pitcher Edwin Jackson is still jobless, so even after hooking Prince Fielder up with a mega-contract, the winter's work of agent Scott Boras is not yet complete. At this late stage, the chances of Jackson signing to any kind of surprisingly-large deal are slim, as budgets are mostly at their end across the league, and teams are starting to focus on what 2012 will bring. It's more likely Jackson has to take what Boras affectionately refers to as a "pillow" contract -- one that will give him a job in the present, and possibly set him up for a bigger payday in the future.
Another Boras client, Ryan Madson, ended up settling for one of these pillow deals with the Reds, after the only team willing to spend big money on a closer threw it at Jonathan Papelbon. Madson will bring be paid $8.5 million, months after almost signing a four-year, $44 million contract with his original team in Philly.
Jackson isn't as good as Roy Oswalt, and maybe not as good as Gavin Floyd, but at this stage, he likely would be cheaper than either: Oswalt is reportedly looking for around $8 million per year, and Floyd, while inexpensive monetarily in terms of the luxury tax, will cost the team in prospects. At the least, he is durable, averaging 208 innings per year over the last three years, and 202 over the last four, and his ERA+ since he left Tampa Bay is an above-average 108.
Should the Red Sox attempt to sign Jackson to a one-year deal to finish off their rotation, or is the risk too high that, if they were to extend a qualifying offer to him for 2013 following his free agency, he would accept when the league shows itself uninterested in his price tag once again?