Let's face it. We are 9 games behind the last Wild Card slot with 6 teams between us and that 5th playoff slot. We are done for 2014.
Trading prospects to make a push for the playoffs would be pointless and wrong.
Trading for a player under team control for several years is a possibility this deadline, but not likely.
We have to look at improving out future as best we can and at least get some value out of this lost season.
I know it is not common for a team to several players at the deadline, but we have to try our best to get something for players that have no future with the Red Sox after this year. Here's a player-by-player rundown of what I think we need to do:
Lester: We need to try and extend him or get a framework of understanding before the deadline comes and goes. Reportedly we offered him $70M/4 in the Spring. That is a slap in the face. News is that negotiations have reopened, and the number of $120M/5 has been floated out there as Lester's request. I'm no expert on contracts, but I think we should offer something like $105M/5 with a 6th year team option for $15M with a $5M buyout, essentially making it a $110M/5 or $120M/6 deal. To me, that is fair. Most importantly though, is that we need to know if this is close enough to Lester's lowest demand to feel safe that we will keep Lester in Boston. If we feel like we are too far apart, we have to trade him. It's really essential that we get more than a comp draft pick, if Lester walks. It might take us years to recover losing Lester for next to nothing in return. Teams would give a lot for 2 months and a playoff cycle of Lester. They would give even more if we allowed them to negotiate an extension. Either way, a trade would bring us more than the value of an extra draft pick.
Uehara: Koji will be 40 on opening day 2015. I'm not usually one to use small sample sizes to judge players, but one has to wonder if he is has started to or is due for an age-related decline in performance level. I definitely want Koji back next year, but unless we are fairly certain he will be back, we need to trade him as well. There are many contending teams out there that might think he is the guy to put them into the driver's seat. We could get a very nice prospect for Koji.
Peavy: I'm not sure what offers might be out there for Jake, but I'm pretty sure that if we paid a good chunk of what he is still owed (about 3 to 4 of $5M), we could get a prospect with some promise in return. Let's roll the dice and hope what we get back turns out to help us going forward, if not, at least some young starting pitcher in our system will get a chance to show what he's got in the bigs for a couple months.
Drew: Doubtful anyone wants him, but offer to pay a good chunk of his deal and see if there is a taker.
Pierzynski: Doubtful anyone wants him, but offer to pay a good chunk of his deal and see if there is a taker.
Gomes: Jonny has very good numbers vs LHPs this year and over the last 5 or 6 years. Some team out there is in need of a platoon OF'er with reportedly good clubhouse karma. Get what we can and trade him for the best offer. Let Holt, Betts, JBJ and maybe even Cecchini, Hassan or others get some (more) ML PAs for a couple months.
Ross: Doubtful anyone wants him, but offer to pay a good chunk of his deal and see if there is a taker. (If we trade AJ P, we may want to keep Ross to mentor Vazquez or Butler.)
Badenhop: Burke is on pace for one of his best seasons. He's right up there in IP among RP'ers and has good trade value. Get what we can for him.
Miller: There are a few teams with a big need for a LH'd Rp'er. Miller has been one of the best for a 2 year period. We can get something good for him. Do it.
Free Agents after 2015: Napoli, Victorino, Mujica
Ortiz $10M for 2016 and 2017 with bonuses
Buchholz has an option for 2016 $13M ($245K buyout) & 2017 $13.5M ($500K buyout)
I hate to say it, but it is "firesale" time. We have 10 players who will be free agents unless we extend them. I seriously doubt we can trade even 8 of them, even if we try, but we should do our best to deal all the ones who won't be back next year.