When Roy Halladay signed his extention with the Phillies, Cliff Lee became the top free agent on the 2010 market. He's coming off two Cy Young caliber seasons at age 29 and 30, but he was pretty pedestrian before that. While we're confident that Lee won't sign at a discount in Seattle, he's not CC Sabathia.
Josh Beckett might still work out a deal in Boston, but with his injury history (back and hands), the $85M deal the Sox just gave John Lackey, and the emergence of Jon Lester, the Red Sox might be willing to let Beckett take offers on the open market. Unless someone offers a Tom Hicks-Arod overpay, the Red Sox can be confident that they'll be able to match any final offer.
A year ago, Brandon Webb was the top pitcher on this list. As of December 2008, Webb had averaged 227IP for the last 5 seasons, a 1.25 WHIP, a sinker worth 0.6 HR/9IP, and 7.1K/9. An impingement in his shoulder left some people wondering if the D-backs would pick up his $8.5M option for 2010 (they did). We'll have another year to watch him try to ensure his career is more Mike Mussina and less Ben Sheets.
One thing we haven't talked about yet: the Yankees have to sign at least one of these starters. C.C. Sabathia will be a free agent after the 2011 season. He might not significantly beat his current deal in dollars, but just like Arod, he can find someone (maybe the Yankees) willing to extend it through the end of his career.
One thing I didn't like about last offseason was A.J. Burnett's deal. Yes, he was the second best starter on the market, and yes, the Yankee needed him. Everyone knew that. So the Yankees offered a 5th year ever though no one else was in that neighborhood. And this year Lackey wanted the same contract. The Yankees have less need this year, but someone was willing to give Lackey his price (in years; I really don't care about dollars).
One (or more) of the pitchers on this list are going to get a Sabathia/Santana deal. I'm not sure any of them are really worth those many years. But the Yankees backed themselves into a corner when the ink dried on Burnett's contract. As we've learned so many times, you can't spend your way out of mistakes- everything has to go right with the development of Joba and Hughes. I hope it's not asking for too much.