This is a puzzle, so I will probably be wrong on nearly all of these, but let's do it just for fun.
1. Matt Holliday—Red Sox
The Red Sox have lots of money just like the Yankees, and they won't hesitate to offer Holliday a seven- or eight-year deal worth $100-150 million. The Yankees already have both Matsui and Damon and will re-sign one of them for sure, so they won't sign Holliday.
2. Jason Bay—Mets
The Mets need a left field slugger, and they will be fighting hard for both Holliday and Bay. Boston would most likely beat the Mets out for Holliday, so the Mets can get someone just as good in Bay. Bay rejected the Red Sox's offer, so he will not likely return to Boston. He will likely sign a seven-year contract worth about $100 million.
3. John Lackey—Yankees
The Angels have a dilemma between Lackey and Figgins. Lackey is likely to ask for more money, so the Angels will not likely be able to meet his demands as they have already spent money on re-signing Bobby Abreu. The Yankees can afford anyone, and Lackey won't be able to resist lots of money from the World Series champions with CC Sabathia and A.J. Burnett. With Lackey in the rotation, the Yankees could be immortal.
4. Chone Figgins—Angels
The Angels are one of the best teams in baseball when it comes to speed, and Figgins is the main reason for that. The Angels will want to get their leadoff man back. He's one of the best leadoff men in the majors, and he has incredible speed.
5. Rich Harden—Twins
The Twins have openly expressed interest in Harden. He is injury-prone but very effective when healthy, and he would bolster the Twins' rotation a lot. Harden would provide good depth for the rotation with Slowey, Baker, Perkins, Blackburn, and Liriano already on the roster.
6. Randy Wolf—Phillies
Wolf has had some really bad luck with the Dodgers. Whenever he had good games, he pretty much always got no or little run support. He had a 3.23 ERA but only 11 wins. He will probably not want to stay where he has had bad luck, so why not go back to his old team?
They are the defending National League champions and could win another World Series with him in the rotation.
7. Andy Pettitte—Yankees
The Yankees would not let their veteran pitcher that can serve as a mentor to the younger players leave. He will probably sign a one or two-year deal and then retire.
8. Marco Scutaro—Red Sox
The Red Sox need a shortstop, and they are not likely to re-sign Alex Gonzalez, and Jed Lowrie won't cut it as a starter. Scutaro is a consistent hitter and can produce runs while not a power hitter.
9. Jose Valverde—Cubs
The Cubs' closer Kevin Gregg is a free agent and will not likely return, so they can offer Valverde a hefty contract and get an upgrade at closer. Valverde has some really bad moments here and there but is overall a reliable closer.
10. Jermaine Dye—Giants
The Giants could use some power in their lineup, and Bengie Molina is most likely leaving, and Dye would make a good upgrade over Randy Winn.
11. Adrian Beltre—Orioles
Melvin Mora is a free agent, and the Orioles will be looking for another third baseman to give them 20 home runs.
12. Johnny Damon—Yankees
Damon won't leave the team he just won a World Series with, and they have all the money to bring him back.
13. Hideki Matsui—Yankees
Matsui is the kind of player that plays with only one team his whole career, and the Yankees will definitely want their World Series MVP back.
14. Joel Pineiro—Cardinals
The Cardinals need to keep their rotation intact, and they will be able to offer Pineiro plenty of money if they sign neither Holliday nor Bay.
15. Marlon Byrd—Rangers
The Rangers will want Byrd back, and not too many teams need a center fielder.
16. Orlando Hudson—Cubs
The Cubs need a reliable second baseman, and Hudson would fix the hole up the middle.
17. Mike Cameron—Padres
The Padres need an outfielder, and Cameron is a good short-term bargain that can hit 20 home runs.
18. Miguel Tejada—Reds
Tejada will not want to stay in Houston, so he will test free agency, and the Reds are in dire need of a shortstop, so they will do what they can to grab Tejada.
19. Erik Bedard—Cubs
The Cubs will need a pitcher to replace Rich Harden, and Bedard is pretty similar. He is injury-prone but can throw many strikeouts when healthy like Harden.
20. Bengie Molina—Mets
Molina is most likely leaving the Giants, and the Mets need a catcher. Molina is capable of hitting 20 home runs and 90 RBIs.
21. Orlando Cabrera—Tigers
The Tigers need a shortstop, and Adam Everett isn't the solution, so he will be let go, and Cabrera will provide defense and a jolt to the offense.
22. Aroldis Chapman—Angels
Chapman is a Cuban defector, and so was Kendry Morales. The Angels will not likely get Lackey back, and if they don't get Halladay, they can get Chapman. He will be a diamond in the rough just like Morales.
23. Jason Marquis—Rockies
The Rockies had solid starting pitching last year that got them into the playoffs, and Marquis will want to stay with a contender.
24. Mark DeRosa—Phillies
The Phillies have been pursuing DeRosa, and they could use him at third base, and he is better than Pedro Feliz.
25. Adam LaRoche—Rangers
Chris Davis proved last year that he is not ready to handle the first base job with his many strikeouts at the plate, so they will look for a short-term solution to give Davis more time to get it together.