So here we are, 90 games in and the sox are on pace for a repeat of 2012. Right now, they are on pace for 70 wins. That being said, they have a lot of kids who could benefit from auditions and the sox could benefit by moving some over the hill vets to desperate teams at the deadline.
My recommendations...
DEAL NOW
I'd deal Lester right now. Lester isn't signing with the sox, the sox tried to negotiate a low ball deal, Lester decided to see how things worked out, and he is having an ace like season. This is the first yr he's averaged a K/IP since 2010. He's on pace for another 200IP season, which will be 6 out of 7. ERA and WHIP would be career lows. With Samardzija off the market, Lester would be the gigantic get and probably a bigger name to go than Price. We know you aren't moving him to NY. But where could he go? One possibility is Seattle. You've got a team dying to get back to the playoffs who is stocked with young pitching talent. Currently, they have a rotation of Felix, Iwakuma, Elias, Young, and ???. Elias is unpredictable, Young cannot be counted on. You add Lester into that 2 hole and you have a team with a very dangerous rotation. It works for Lester too, as he gets to go home. Any deal would presumably have to start with Taijuan Walker, but DJ Peterson is an intriguing player as well. 22 yr old 3B who is up to AA right now and has hit 21HR on the yr with a .967OPS. Either way, the possibility of grabbing a potential front line starter like Walker or a middle of the order CIF has to be better than the 30-something pick in the draft.
I'd also deal Uehara. The guy is 40 and he is healthy and dominating. He isn't part of any rebuild. That being said, he is probably the best closer in baseball right now. The Halos need relievers more than ever, but don't have the MiLB goods. The other LA team is your target. If you could package Uehara with someone and get Joc Pederson, you might find a corner OFer with power you've been craving for awhile now.
I'd deal Peavy to anyone willing to take anything for him, even willing to eat money if you can get a piece you can live with. You aren't offering him a QO
DEAL AFTER THE SEASON
Mike Napoli- There is no point to dealing a slugging 1b mid season since you typically overpay for pitching at the deadline and underpay for offense. Also, he'd probably be the most sought after CIF this offseason with nobody else really out there (Sorry Kendrys and Headley). It also gives you an extra yr to determine your direction. The above 2 guys are gone at years end, anyway. If you decide to make a run at 2015, maybe you keep Nap. If not, maybe you deal him.
Shane Victorino- He just hasn't been healthy. Dealing him now is not a good idea. Dealing him after the season, assuming he finishes the yr well would maximize his value without pulling away PT from your kids.
DEAL ONLY IF IN A FULL REBUILD
Ortiz- He is finally showing his age and another yr on top of that isn't going to be kind to him as he reaches 40. Someone will be desperate, and if he wants to win and the sox are obviously going into a rebuild, you gotta let him out and get something back for him.
Pedroia- I was tempted to put him in the "after the season" list, but I wont. Yes, he is the heart and soul of your team. But he is a little guy on the wrong side of thirty signed for a long time. You deal him this offseason, and you can play 2014 off as an adjustment yr back from surgery. He comes out in 2015 as a .280 hitter with no power and he's a has been. That being said, he is still far above average for his position and if the team sees improvements on the trade or FA market, he's a keeper no question.
Buchholz- I don't deal this guy until he is cruising again. We all know it wont last, but if you deal him now, you're eating money and getting nothing back. If he gives you another 15 game stretch where he's sub 2ERA, then you maximize your profits and move him. That being said, a full out rebuild means you wont have a rotation spot for him and holding onto him is worse than dealing him.