I've been working on this for a bit, here's where I go:
Example1's 2010 Offseason Assessment:
Contracted Players:
C- Martinez (Varitek)
1B- Youkilis (Kotchman)(Martinez)
2B- Pedroia
3B- Lowell (Youkilis)
CF- Ellsbury
RF- Drew
DH- Ortiz
BN: Hermida (OF)
BN: Varitek ©
BN: Lowrie (SS/3B/2B )
BN: Kotchman (1B )
SP: Lester
SP: Beckett
SP: Buchholz
SP: Matsuzaka
SP: Wakefield
RP: Ramirez
RP: Delcarmen
RP: Okajima
RP: Bard
RP: Papelbon
Needs: SS, LF, RP, RP
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Where the Sox stand:
Offense: Red Sox 3rd in RS in 2009:
Yankees (915)
Angels (883)
Red Sox (872)
Phillies (820)
Twins (817)
Rockies (804)
Rays (803)
Pitching/Fielding: Red Sox 11th in RA in 2009: 3rd in the AL
Mariners (692)
White Sox (732)
Red Sox (723)
Rangers (740)
Tigers (745)
Yankees (753)
Rays (754)
Red Sox 3rd best X W-L in MLB:
Dodgers (99-63)
Yankees (95-67)
Red Sox (93-69)
Angels (92-70)
Phillies (92-70)
St. Louis (91-71)
Atlanta (91-71)
I think that offers a pretty good idea of where the team stands on the field. They played like an uninspired group at times last year, but overall they were a very good club. They weren't as good as the World Series teams, but that's a high standard to hold. This team accomplished a lot despite some minor injuries (Youkilis, Bay, Lowell, Lowrie, Wakefield, Beckett, Baldelli) significant slumps (Ortiz), s***** play (Varitek, SS position,) and under-preparation (Matsuzaka, Penny/Smoltz).
They have added what seems to be "MLB Ready" Clay Buchholz and a newly dedicated and embarassed Matsuzaka to the rotation that includes two excellent, World Series caliber pitchers already. At its finest, the Sox rotation is as good as any in baseball. They have also added Victor Martinez for an entire season, which I believe gets overlooked too often. He was a great acquisition for them.
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Filling the Sox Openings:
Shortstop:
They will probably end up resigning Alex Gonzalez and splitting time between he and Lowrie. That would be the safe option. Obviously they will explore the waters for elite SS like Hanley or Reyes, but if that type of player isn't available I don't think they will do anything that would block Jose Iglesias.
Left Fielder:
I've made it clear that I prefer Matt Holliday. I prefer him because I think he's better to build around, but I don't think poorly of Jason Bay. I just like Holliday better. I would be surprised if they didn't offer him at least $18m/yr for 5 years. He's worth it. He's a player I wouldn't be surprised if they topped $20m for and landed and took a lot of criticism for. I think the nay-sayers would be proven wrong in a year or two.
Two Relief Pitchers:
Last year they had a great bullpen and it carried them through some tough times. I think they can keep that going without too much difficulty. Great for SPs, great for the playoffs, great overall.
*Offer Billy Wagner arbitration (which apparently he's open to discussing now). He may accept it (in which case you pay a bit more money to have an established LH closer) or he turns it down and signs elsewhere (in which case you may get compensation), or he turns it down and can't sign elsewhere and he can be signed for cheaper than arbitration.
*If they can't get Wagner they could also look at Mike Gonzalez, LH pitcher.
*They have some internal options too (Dustin Richardson maybe) who could be servicable.
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Other Moves to Make:
I think that this team is in really good shape long-term.
Prospects Available
The only prospects I would not move at this point in a deal are Iglesias (because a plus-defending Cuban SS is valuable), and probably Tazawa for political/franchise image reasons. I would only include Ryan Westmoreland for Adrian Gonzalez or Felix Hernandez (among those who might be available). I only hear good things about him and think he could be a superstar, which can take a franchise from very good to dynasty very quickly.
Trade for Roy Halladay
Make a really solid run at Roy Halladay without giving up the prospects listed above or Buchholz. I think it is possible with something like Kelly, Bowden, Stolmy, Anderson/Rizzo and Reddick/Kalish. That's a huge price to pay, but Halladay immediately makes this team considerably better and a beast in the playoffs. They may need to overspend to get past the Yankees, but the Yankees can have Lackey instead.
Getting Halladay probably also makes Buchholz expendable in another deal if something really great comes along (Felix, Gonzalez, Prince Fielder or Hanley, for instance). Otherwise their rotation would be unbelievable for 2010:
Halladay
Lester
Beckett
Buchholz
Matsuzaka
Get Aroldis Chapman
Another way for this team to add an impact player would be to be aggressive and sign Aroldis Chapman. They will end up paying him a fair amount to outbid the other teams, but it would be a move that generates buzz for the franchise, officially opens an international market of potential Red Sox fans, and would add a young, high-90's, lefthanded arm to a relatively young core. It sounds like the kind of thing Theo would be very interested in doing to pay off 2-3 years from now.
Combined with Iglesias it would give them two young Cuban stars for their primes and, if it works out, the $6-9m/yr he gets paid could be worth it in increased influence in baseball-crazy Cuba. Apparently (according to BP) he and Iglesias are friends--perhaps that would influence him.
Moves like that seem critical to allow this club to compete with the Yankees. International FAs are one place that the Yankees DON'T blow other teams out of the water. They pay very well, but they dont spend hundreds of millions. They had to swallow a bad deal like Julio Lugo, and I would say Chapman's upside is probably higher.
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That's about it...
Overall Summary
*Sign Holliday or Bay.
*Fill the RP spots (preferably with Wagner as one option),
*Trade for Roy Halladay,
*Sign Aroldis Chapman.
It may sound fantasy baseball-ish, but it seems entirely reasonable. We know they are interested in Bay or Holliday. We know they are interested in Halladay. We know they have kicked the tires on Chapman. We know they don't want to just sign FAs to sign FAs. I don't see Lackey or Chone Figgins or many of the other players as very good options given this FO's track record.
A lot of money would come off the books in 2011 (including Halladay) and none of the above moves would handcuff them for the future.
Ellsbury
Pedroia
Holliday
Youkilis
Martinez
Ortiz
Lowell
Drew
Gonzalez
(specific order is debatable)
Halladay
Lester
Beckett
Buchholz
Matsuzaka