Lackey is, surprisingly, the best starting pitcher on the market this winter, and therefore is the hardest to predict where he'll go. Any team with any sort of payroll flexibility, even mid-market teams that are starving for pitching like the Brewers and Nationals, are going to throw their hats in the ring on this one. If I didn't think that Boston was going to go after Halladay and several other free agents, I would say he'd be a sure bet to land there. For now, I'll say the Tigers - they don't have a lot of payroll coming off the books this year, but they're probably losing Washburn and Edwin Jackson and will need a starter. They have a great manager and a good team, but there's always that X-factor with Detroit though - who would want to live there?
2. Matt Holliday, StL - to Red Sox
This is the reason I think that Lackey will land in Detroit - because Boston will spend all of its money on Holliday. St. Louis simply doesn't have the payroll to resign DeRosa, which they desperately need to, and Pineiro or another starter. If they don't end up getting Holliday, I'm sure they get Jermaine Dye or Hank Blalock.
Harden seems to be getting overlooked by a lot of analysts for some reason, possibly because everyone including myself thinks he will resign. The Cubs have the money to resign Harden, and there's not a lot else out there on the market, so I think they'll offer him somewhere in the 4yr/$50-60 mil range, some time after Lackey gets signed.
4. Mark DeRosa, StL - resigns with Cardinals
Mark is that player that every manager wants on their roster. Smart, tough guy who can hit anywhere in the lineup and play several positions well. The Cardinals have shown no interest in bringing Glaus back, so I think he'll be back with the Red Birds next year.
5. Jason Bay, BOS - to Blue Jays
Bay rejected an initial $60 million contract offer from the Red Sox this past week, and I even doubt that he's worth that much. I think that he's a slightly above average hitter and fielder that flourished at Fenway Park. He will command a lower salary than Matt Holliday and will generate a lot of interest as a cheaper left field option. The Blue Jays dumped Alex Rios' entire absurd contract onto the White Sox last year on waivers and will probably trade Halladay at mid-season, and Jason is from Canada. This seems like a good fit to me. I think the Mariners and Mets are going to be big players for him, too.
6. Miguel Tejada, HOU - to Reds
I don't necessarily think that Tejada is one of the top 10 free agents out there, but I list him because he's the best viable shortstop option on the market. A lot of teams are looking for a shortstop, most notably Cincinnati and Boston. I don't think he'll get a big offer from Houston because of their already powerful and old lineup. I'm gonna go on a limb and say he signs with the Reds. They have a lot of young position players and he could bring it all together.
7. Mike Cameron, MIL - to Yankees
This is the pick I feel the most confident with. He was almost traded to the Yankees for Melky Cabrera last year, and the Yankees will be losing between one and four outfielders this offseason. Cammy also fits the mold of all the "great clubhouse guys" the Yanks signed last year. Seems like a no-brainer.
8. Jermaine Dye, ChW - to Braves
Another great free agent outfielder this year. If any of my picks of Holliday to Boston, Bay to Toronto, or Cameron to New York fall through, Dye would go to one of those clubs, and will probably get offers from all three. I'm going to go ahead and assume that I'm right, and that leaves Atlanta, San Francisco, Colorado, and the Mets all possibly needing outfield help as well, and I will choose the Braves as the team that comes out on top. There have been a number of reports about Atlanta trying to trade Derek Lowe for an outfielder, and I think this would be a better route for them to go.
9. Randy Wolf, LAD - to Brewers
The Brewers are going to go hard after almost every single pitcher on the market this year, and this is the guy I think that they will sign, along with Mark Mulder. Brad Penny and Pedro Martinez are too much of injury risks with them already signing Mulder, and Ben Sheets doesn't seem to be interested in a return to Milwaukee. That leaves Brett Myers, Jarrod Washburn, and Wolf, and the latter seems more feasible to me. I think Myers is only useful as a bullpen pitcher, and Washburn will sign with the hometown Twins.
T-10. Vladimir Guerrero and Hideki Matsui, LAA/NYY - Angels/Mariners
I put these two tied for last because they're similar players - both once great hitters that are now on the decline, and may not physically be able to play the outfield anymore. This pretty much limits potential teams to the 14 in the AL. You might see these two go down to the wire like Bobby Abreu did last year. I think that the Angels will make every effort to resign Vlad and Chone Figgins. The Yankees will probably resign Damon and let Godzilla go. If Hideki proves he can still play the field, he signs with the Mariners, otherwise he will probably retire.
I put these two tied for last because they're similar players - both once great hitters that are now on the decline, and may not physically be able to play the outfield anymore. This pretty much limits potential teams to the 14 in the AL. You might see these two go down to the wire like Bobby Abreu did last year. I think that the Angels will make every effort to resign Vlad and Chone Figgins. The Yankees will probably resign Damon and let Godzilla go. If Hideki proves he can still play the field, he signs with the Mariners, otherwise he will probably retire.