Choose your own adventure: you're the GM!

-6 key objectives to this off-season's success. Market Aggressiveness,$$ Sensibility,Regain Health,Renew Chemistry,Balance,and Leadership.
-$48M to spend,$10M cushion.

*1 SP in FA:     *Plan A- Hardsell J.Lester!!         Start with 6/138M...max out at 6/150M no opt. yrs.      *If that fails then...
                       *Plan B- Overpay for J.Shields.   Start with 4/92M-4/100...max out at 5/115.                 *Gotta get 1 or the other!

*1 RP in FA:      A.Miller 4/48M -Setup/Eventual Closer.

*Must Do* Off-season   TRADE:           Y.Cespedes,D.Merrero -for- J.Niese,D.Murphy
*Possible* Mid-season   TRADE:           H.Owens,J.Bradley,D.Nava,W.Middlebrooks,A.Webster -for- J.Heyward,J.Walden

[LINEUP]:For Now           [BENCH]:For Now               [STARTERS]                         [BULLPEN]:For Now                        
1.Castillo CF                                                          1.Lester/Shields                     -Uehera     CL                                 
2.Pedrioa 2B                  - Holt         INF/OF            2.Neise                                  -Miller        SU
3.Murphy 3B                  - Craig       1B/OF              3.Buchholz                             -Tazawa     SU
4.Ortiz DH                     - Victorino  OF                   4.Kelly                                   -DeLaRosa MR/LR
5.Napoli 1B                    - Butler      C                     5.Johnson                              -Ranaudo  MR/LR                                 
6.Nava LF                                                                                                          -Workman MR/LR
7.Betts RF                                                                                                          -Webster   MR/LR
8.Bogaerts SS                                                                                                     
9.Vazquez C

Lester, Headley, Maeda or McCarthy. Done, except for depth, like backup catcher, bullpen, minor league signings and such.

I don't see an urgent need to trade anyone/for anyone. If the right trade presents itself I'd look into changing my game plan. I think we match up well with Mariners and Braves, and to the Mets and Marlins as dark horses.

P.S. Not sure if we are considering Moncada as he won't contribute in 2015 but I would be all over that.


ADD: about 6 months ago I really liked the idea of Betts playing SS and Bogaerts moving to 3B. I still really like this idea although it does not seem to be an option, with Bogaerts seeming uncomfortable at 3B and Betts being shifted to the outfield. To me Betts profiles as a middle infielder, and Bogaerts doesn't seem long for SS. This doesn't seem like a realistic possibility anymore (or ever), but it would be an interesting way to solve our 3B hole and OF jam internally.

Heyward will not be extended by the Braves. My thinking is this. Their OF will be in shambles. Allen Craig can play there. Nobody thinks his struggles will continue. Injuries have plagued him. So they get 3 years at 6 mil per for Craig.

Cherington is on record saying people view Bradley as a starting CF. He will start and win Gold Gloves in CF.

Marerro is already MLB ready as a SS. He could play 2B for Atlanta as well since they just dealt La Stella to Cubs.

Currently their 3B is occupied by a stop gap with no power. Middlebrooks would at least give them 20+ HR power from the corner.

You see these guys as failures, however, MLB GM dont always think that way. You can always change out someone for Barnes or Brian Johnson, Id give them Betts straight up for Heyward.

Craig - "Nobody thinks his struggles will continue" Very confident of you. Also, at least some (I don't over commit) think he's a 1B and shouldn't be in the OF (now granted, he wouldn't have to play RF as J Upton could move over)

Marrero - His greatest value is that he's MLB ready at SS . . . but Atlanta is going to move him to 2B (where, btw, one of their top prospects plays), diminishing his value

Bradley - What is Cherington supposed to say? "Yeah, he's really not that good but . . . give us a lot for him". I, personally, wouldn't recommend using what a GM says (especially around any trading time) as a metric for the value of a player.

Welcome to Soxprospects bstrong!

Yes. Didn't mean to pick at one of your first posts. Just highlighting what I felt were some potential issues with the ideas.

Full disclosure, I definitely thought they could get more than what is being reported so do with that what you will.

Crazy thing is they got less for him than what I offered.

Uh, Marrero was your headliner, not even close to a better package.

I would like to change my thought process and now we add some more pieces for Dominic Brown in Philly deal.

I suspect the Sox weren't even bidders for Heyward. OF is not where they are focused. I think they are making big pitches for Sandoval, Lester and Hamels, and won't do much else until those deals are either done, or fail.

Heyward was not a favorite of mine, but I think he will help the Cardinals.

My approach as a GM would be similar to what I think the Sox are doing in reality.
However, I suspect that Sandoval is just using the Sox to get a better deal from SF and he will take their best offer. I think Headley is going to be signed by the Yankees. I think 3B is going to have to be filled internally for the time being, and I would try Betts there.

Trade: Cecchini, Brentz, Buchholz and either Johnson or Owens to the Phillies for Hamels, maybe adding one or two of the better lower minor league prospects, but not Margot or Devers.

FA signings: Lester and Shields, a LH RP, maybe Miller if there is enough money.

Lineup

Betts 3B
Victorino RF
Pedroia 2B
Ortiz DH
Napoli 1B
Cespedes LF
Bogaerts SS
Castillo CF
Vazquez C

Bench
Craig
Holt
Nava
Butler or Lavarnway

SP
Lester
Shields
Hamels
De La Rosa
Kelly

RP
Uehara
Tazawa
Mujica
Workman
Layne
Barnes
LH acquisition (Miller?) or Britton

You picked literally the worst position player in the majors last year to go after to fill a position we need the least.  He has negative WAR for his career and he's 27.