A note before we begin – this is a complicated puzzle, and I’ll be satisfied if I’m correct on a quarter of these guesses. If your favorite team seems under-represented, keep in mind that the list doesn’t account for trades or every single free agent.

1. Matt Holliday – Mets. The Mets could grab headlines by signing Holliday to a six or seven-year deal for more than $100MM.

2. John Lackey – Yankees. Last winter’s strategy of signing the best two starters and the best hitter available contributed to the Yankees’ World Series title. With rotation question marks after C.C. Sabathia and A.J. Burnett, it makes sense that the Yanks will pursue the best available starter in Lackey.

3. Jason Bay – Red Sox. It’s been rumored the Red Sox are willing to offer four years and $60MM to Bay. That seems to be a fair opening bid, given his defensive struggles.

4. Chone Figgins – Angels. The Angels have internal options at third base, but he’d be hard to let go after a career-high .395 OBP and excellent defense at the hot corner.

5. Randy Wolf – Mets. The Mets regrettably chose Oliver Perez over Wolf a year ago. As the best available starter aside from Lackey, Wolf is primed to get a three-year deal worth more than $30MM.

6. Andy Pettitte – Yankees. With all the good vibes surrounding Pettitte’s work this year, it’s hard to see him anywhere else. The Yankees might have to guarantee more than $5.5MM this time though.

7. Jose Valverde – Phillies. One way to shore up a shaky bullpen: sign the best closer available. Few teams are seeking closers, and even fewer have money, so the Phillies should be able to get a relative bargain.

8. Marco Scutaro – Red Sox. It’s difficult to place Scutaro, because not many teams with shortstop vacacies will be willing to pay the three years and $18MM+ he’ll likely demand. The Sox would be getting the best available shortstop here, but they could instead choose Jed Lowrie and/or Alex Gonzalez.

9. Adrian Beltre – Twins. The Twins made a large upgrade at shortstop by acquiring J.J. Hardy. Beltre would give them fantastic left-side infield defense and another possible 20 home run bat. The Twins had interest in trading for Beltre a year ago, though the Scott Boras client added them to his no-trade clause.

10. Rich Harden – Red Sox. A one-year deal with a $7MM base salary would be difficult for Harden to resist. His injuries are maddening, but he leads free agent starters with a 10.9 K/9.

11. Mike Cameron – Padres. The Padres are tight on cash, but bringing back Cameron to play center field makes sense on a one-year deal worth $7MM or so.

12. Johnny Damon – Yankees. Most believe the Yankees will re-sign one of Damon and Hideki Matsui. Despite Matsui’s World Series MVP award, Damon probably fits better given his ability to play the field more regularly.

13. Orlando Hudson – Nationals. The Nats coveted Hudson last year. Adding him now would help with their stated goal of improving up the middle.

14. Miguel Tejada – Athletics. A one-year deal to bring Tejada back would give the A’s security on the left side of the infield, where they have Cliff Pennington at shortstop and Brett Wallace not quite ready at third base.

15. Joel Pineiro – Cardinals. He’d be a big loss for the Cardinals, who have rotation openings after Chris Carpenter, Adam Wainwright, and Kyle Lohse. Pineiro walked just 27 in 214 innings posted a 60.5% groundball rate due to a newfound sinker.

16. Nick Johnson – Giants. A jolt of OBP at first base would do the Giants good. They were involved in talks for Johnson around the trade deadline.

17. Aroldis Chapman – Red Sox. They’ve been heavily involved with Chapman from the start, and may consider him a long-term investment worth more than $20MM.

18. Marlon Byrd – Rangers. Byrd is one of the better center fielders available, but not too many clubs are in the hunt at the position. The Cubs could be in the mix here after they trade Milton Bradley.

19. Vladimir Guerrero – White Sox. The White Sox would generate attention by signing Vlad as a DH and occasional right fielder. Landing Guerrero would also be a solid baseball move on a reasonable one-year deal.

20. Felipe Lopez – Dodgers. They seem ready to part ways with Orlando Hudson, and Lopez might be a bit cheaper. Lopez’s 2009 season ranked fourth among all free agents in WAR.

21. Adam LaRoche – Braves. Did LaRoche’s scorching stint with the Braves last year price him out of their range? The Mets, Orioles, A’s, Mariners, Giants, D’Backs, and Rangers might also be in the market for a first baseman.

22. Rafael Soriano – Angels. Will the failure of Brian Fuentes prompt the Angels to add another late-inning arm? After missing most of ’08, Soriano bounced back with 102 strikeouts in 75.6 innings this year.

23. Jon Garland, Dodgers. Bringing back Garland would be a safe move, though the Dodgers already declined his $10MM option. Garland required a $7.25MM guarantee a year ago, and he had a better season, so this is an iffy prediction. The Twins, Nationals, Mets, and Brewers may be among the other teams seeking an innings-eater.

24. Carl Pavano – Nationals. Back to his original organization? Pavano surprisingly managed 33 starts in ’09, and his 4.16 xFIP reveals his 5.10 ERA was misleading.

25. Brad Penny – Mets. Penny is just one of many different arms the Mets might consider as they attempt to bolster their rotation depth. No other free agent starter throws harder, so Penny’s upside is still tantalizing.

26. Erik Bedard – Dodgers. If the Dodgers don’t want to pony up the cash or prospects for a true ace, they could buy a Bedard lottery ticket instead.

27. Hideki Matsui – Mariners. Matsui joining the Mariners in a DH/left field role will become more likely if Ken Griffey Jr. retires.

28. Bengie Molina – Nationals. Molina is difficult to place, especially if he demands more than $5MM. With Jesus Flores coming off shoulder surgery, the Nats will probably add a veteran on a one-year deal. The Mets also may sign a catcher.

29. Mike Gonzalez – Braves. Gonzalez should be cheaper than Soriano, and the Braves need some kind of relief signing or acquisition. With available closers plentiful, the Braves could wait around until March in hopes of a bargain.

30. Jason Marquis – Diamondbacks. The D’Backs are known to crave a mid-tier veteran starter, and Marquis is one of many options. Many have speculated Marquis would like to play for the Mets, and they are a reasonable match as well.

31. Placido Polanco – Diamondbacks. Second base is another area of need for Arizona. As with the Marquis situation above, Polanco is one of several palatable free agent choices.

32. Tim Wakefield – Red Sox. Wakefield had back surgery in October, but the Red Sox will probably still view him as a bargain at $4MM.

33. Ben Sheets – Rangers. The Brewers and Rangers seem to be the most likely landing spots for Sheets, who had flexor tendon surgery in February and missed the ’09 season. That injury caused a two-year deal with the Rangers to fall apart.

34. Doug Davis – Brewers. Davis was claimed off waivers by the Brewers in August, but they couldn’t work out a deal with the D’Backs. At the time, Davis liked the idea of returning to Milwaukee. He’ll probably have to back off his three-year demand to make it happen.

35. Jarrod Washburn – Brewers. Perhaps the Brewers won’t sign these two mid-tier lefties, but they do figure to acquire a pair of starters somehow. Washburn could make it easier on the Brewers by providing a hometown discount. Otherwise, trading Mat Gamel could net an arm.

36. Russell Branyan – Mariners. Interest in a new contract is mutual. There are enough mitigating factors to make another one-year deal likely.

37. Billy Wagner – Cubs. The Cubs don’t have much payroll space, and they may prefer to go with Carlos Marmol as their closer. Then again, they wouldn’t do so a year ago when Marmol was coming off a good season. The Cubs could offer Wagner a chance to close, as could the Orioles, Rays, Tigers, Angels, and Braves. Even Wagner’s old teams, the Phillies and Astros, have back-end bullpen concerns.

38. Juan Uribe – Mariners. Uribe was quietly very valuable in 2009, playing all around the infield for the Giants. Uribe’s shortstop-third base flexibility could fit for Seattle.

39. John Smoltz – Tigers. Smoltz of course came up with the Tigers, and they considered him a year ago. They could sign him and keep an open mind as to his role.

40. Jermaine Dye – Rangers. The Rangers signing both Byrd and Dye might be a stretch, though Dye should be used strictly at DH. Given his second half decline he should be affordable.

41. Mark DeRosa – Phillies. I debated flipping the DeRosa-Beltre predictions, as both the Phillies and Twins have a need at third base. DeRosa, a former Penn quarterback, has been linked to the Phils for years.

42. Coco Crisp – Royals. The Royals already declined his $8MM option. But Crisp likes Kansas City and the Royals still need a center fielder, so an incentive-based deal could happen.

43. Carlos Delgado – Orioles. In Delgado, the Orioles could add a possible 30-home run bat with little risk. And Delgado could benefit from some time at DH.

44. Orlando Cabrera – Blue Jays. O-Cab might find a small market for his services this winter, even without a draft pick cost attached.

45. Gregg Zaun – Rays. Zaun can void his $2MM club option if the Rays exercise it, but he might be swayed by the chance to start.

46. Jim Thome – Athletics. The A’s should have their pick of affordable free agent DHs. Thome’s not done; he hit .249/.366/.481 this year.

47. Fernando Rodney – Tigers. I have no idea where Rodney will sign. No one will want to pay a premium for his 37 saves. He might be best-served returning to Detroit on a one-year deal worth $6MM or so.

48. Xavier Nady – Diamondbacks. The D’Backs will probably tender a contract to Conor Jackson, but Nady could still be helpful at first base and left field. He’s a Scott Boras client, but he missed most of the season due to Tommy John surgery.

49. Kiko Calero – Rays. Calero’s a health risk, so he might be cheap despite a 1.95 ERA and 10.4 K/9 in 60 innings this year. He’s the type of reliever the Rays figure to add.

50. Rafael Betancourt – Rockies. I think the Rockies will work out a two-year deal to retain Betancourt as their setup man. It could include incentives for closing, should Huston Street depart after ’10 or struggle before then.

RE. RANDY WOLF, HE FREIGHTENS ME AS TO WHY AN ‘ON PAPER’ COMPETENT, EFFECTIVE YOUNGISH LH SP HAS BEEN ON 5 DIFFERNT ROSTERS SINCE 2006? CONSIDERING THE VALUE OF COMPETANT PITCHING & HIGHER VALUE OF LH ONES, THAT FACT CERTAINLY MAKES ME WONDER ABOUT THE NON-STATS ISSUES, LIKE CLUBHOUSE FACTOR, PERSONALITY,PERHAPS HE DRINKS TOO MUCH? ETC. HE CERTAINLY DIDN’T IMPRESS IN THE LCS. I STILL SAY WE’LL LIKELY DEAL A SP & IF WE DO SHOULD FOCUS ON LACKEY & MARQUIS FOR #2 & #3 SPOTS BEHIND JOHAN & IN FRONT OF OLLIE(SEE CONTRACT EATING ISSUE ABOVE) LIKE CASTILLO OLLIE IS SUPERGLUED ON THE ROSTER, ALL WE SHOULD DO IS ROOT FOR HIS IMPROVMENT UNDER WARTHEN WHILE HOLDING OUR NOSES AS GOOD FANS, ALWAYS REMEMBER IT COULD BE WORSE, WE COULD BE IN CINCY OR PITTSBURGH! MAYBE KC!

The Red Sox trade is a little more confusing as I would rather have Bay or Holliday then Hermida though I think the Red Sox prefer Bay over Holliday anyway.