This is more about 2015 than 2014, but looking ahead is part of what we do today...
We will have a lot of money to spend after 2014.
Lackey will be at the minimum for 2015, unless we rework his deal (extend a year?)
Lester will probably be extended after the season starts so as not to hurt this year's luxury limit number.
However, it will NOT be easy to replace (about $20M total):
These can probably be replaced at a cheaper cost (about $50M for 2014):
Peavy ($14.5M) & Dempster ($13.25M): Workman, Britton, Webster, Ranaudo, Barnes, Owens, Wright, Hinojosa or others.
Pierzynski ($8.25M) & D Ross ($3.1M): Vazquez, Lavarnway, Butler, Swihart, Denny
J Gomes ($5M): Hassan, Brentz (Betts/Cecchini?)
Badenhop (TBA) & Miller (TBA): (see SP list above), de la Rosa, A Wilson, Noe Ramirez, C Hernandez, T Layne, J Ely, Watanabe
Before any signings or extensions, here's what 2015 looks like....
25 man roster (position move or minors):
C: Lavarnway/Vazquez (Butler/Swihart/Denny
1B: Napoli/Carp (Middlebrooks/Snyder/T Shaw)
2B: Pedroia/Herrera (Betts/Rijo/Coyle)
3B: Middlebrooks (Devers)
SS: Bogaerts (Holt/Marrero/Vinicio/Lin)
LF: Nava/Hassan (Carp/Linares/de la Cruz)
CF: Bradley (H Ramos/Margot)
RF: Victorino (Brentz)
DH: Cecchini (Nava/Carp/Lavarnway/Napoli/Betts)
SP: Buccholz, Lackey, Doubront, Workman, Britton, Webster
(Barnes, Ranaudo, Owens, Wright, Hinojosa, de la Rosa,
B Johnson, T Ball, Stankiewicz, L Diaz)
RP: Mujica, Tazawa, Breslow, de la Rosa, Villareal, A Wilson
(Hernandez, Ely, Layne, Watanabe, N Ramirez, Kurcz, Balcom-Miller)
Free agent class for 2015 looks weak? We can make QO to Lester,Ortz and maybe Peavy if he does well this year and no young arm steps up. With qualifying offer, I doubt Ortz will be singable by any other team. Teams that can afford him already have position players in their back end of their contract that will need to shift over to DH (yankees). I would keep signing him for $15M as long as he's around 30 HR and 100 RBIs.
Do we make a run at Hanley? We still have few years before having to deal with Boras for Bradley Jr and Xander Bogaerts.