I hate to even think about it, and even if we are 15 games behind by the deadline, I'm not sure Ben would ever push the total reboot button. Red Sox history has very few instances of unloading high-priced players and/or free agents to be, but there are a few from recent (AGon, Crawford & Beckett) to way back (Slocumb and Wells are two that come to mind).
We have a great farm team on paper already, but trading away a few pieces to desperate GMs still in the race at the deadline could really boost our long term outlook as well as beef up our list of trade assets for a winter blockbuster or two.
Here's a list of high-priced or free agents to be on our current roster:
Pedroia: $110M/8 (Not going to be traded.)
Buchholz: $7.7M then $12M plus 2 team options (Toughest call to make)
Ortiz $16M then $16M and 2 club options (not likely to be traded)
Napoli $16M then $16M in '15 (not likely to be traded)
Victorino $13M then $13M (not likely to be traded, unless we view 2015 as a near lost cause too)
Mujica $4.75M then $4.75M: do it, even if for a stretch of a prospect
Breslow $3.8M then $4M team option: do it
Lackey $15.25M then Min wage next year (not likely to be traded, unless we view 2015 as a near lost cause too)
Lester $13M then FA: Blue chip trade candidate (if we can't extend...)
Uehara: $4.25M then FA: Blue chipper (at his age, should we extend?)
Peavy $14.5M then FA: If he is doing well, we could get a nice return here.
Pierzynski $7.5M: do it, even if for a stretch of a prospect
D Ross $3.1M: do it, even if for a low-level prospect
J Gomes $5M: do it, even if for a stretch of a prospect
Capuano $2.25M: do it, even if for a stretch of a prospect
Badenhop $2.1M, Miller $1.9M and Sizemore $750K + bonues will all be FAs after this year: do it, even if for a stretch of a prospect
I would not look to trade arb players, but here are some that other teams may want: Carp $1.4M + 2 arbs, Herrera $1.3M + 1 arb, Tazawa $1.3M + 2 arbs (I would not trade Taz), Doubront $586K + 3 arbs (stock not high enough now- better to keep and pray), Nava $556K + 3 arbs (doubtful we get a nice enough return to give up on him).
We will not trade all these guys. I'd be surprised if we trade away 1 or 2 for prospects, but the theory is sound, assuming we are out of it by July or the waiver-wire deadline in August.
Assuming all our free agents to be bolt, and no free agents are signed (not going to happen) this is what we are left with for 2015:
SP: Lackey, Buchholz, Doubront, Barnes, Ranaudo (or Owens)
RP: Mujica, Tazawa, Workman, Britton, de la Rosa, Webster, A Wilson
C: Vazquez & Butler (or Lava or Swihart)
1B: Napoli & Carp
3B: Middlebrooks & Cecchini
SS: Bogaerts (3B?)& Marrero (or Herrera or Holt)
LF: Nava & Hassan (or Brentz)
CF: JBJ (Wlkerson?)
RF: Victorino (H Ramos?)
Lots of holes, lots of young players with potential, lots of question marks, but also lots of promise.