I'd put the roster in the following buckets: WITH COMMENTS FOR NEXT YEAR
Not getting traded under almost any circumstances
Ortiz - can block trade, public statements BUT MAY BE RETIRING (OR PLATOONING) IN 2016
Pedroia - can block trade, signed below-market deal to stay in Boston
Rodriguez - multiple years of control, early signs of potential dominance
Betts - have already turned down multiple offers, on pace for 3+ WAR season
Bogaerts - see Betts
Porcello - contract vs. performance to date makes this one highly unlikely - would be ultimate sell-low
Sandoval - contract is tough but more importantly, Sox have zero options to replace him right now AND MAY BE MOVING TO 1B IF ANOTHER 3B COULD BE FOUND
Craig - just a sunk cost at this point IMO
I'D INSERT SWIHART HERE
Unlikely to trade, but possible
Ramirez - see Porcello, but could see a team viewing him with enough upside to take a risk if Sox pay part of freight FUTURE DH, PROBABLY ONE OF THE BEST
Miley - contract is reasonable but market for underperforming #4 starters isn't all that strong
Swihart - struggles to date in MLB notwithstanding, he's still got tons of upside and team control at a premium position I'D REPLACE SWIHART WITH VAZQUEZ ON THIS LINE
Victorino - zero value right now. Seems like a prime candidate for an August waiver deal GONE
Rusney - huge contract but SSS and I suspect scouts still see oodles of latent talent/athleticism RIGHT FIELDER (OR CENTER FIELDER)
Barnes - seems like he has a real future as a late-inning relief ace on the cheap, but not someone I'd refuse to include in the right deal
On the fence
Tazawa - getting more expensive, but a very reliable performer (against everyone but Toronto, at least) CLOSER?
Holt - worth more to us than others, even if part of 2015 performance is just the BABIP gods favoring him
Kelly - some team could see him as the next Wade Davis but probably not getting much for him HE'S CONTROLLED AND IS EVENTUALLY GOING TO BE WORTH MORE THAN HE'S PAID, SOMEWHERE, FOR SOMEONE. HE MAY LEARN HOW TO PITCH.
Hanigan - cheap, fills a role, but if we're going nowhere it's not like he's a part of the future GONE
Layne - multiple years of control, but also the kind of guy who could fetch a good prospect to a desperate contender at the deadline
Wright - minimal trade value, but has usefulness to Sox as innings eater either for spot starts or mop-up duty
Hope they're renting, not owning
Buchholz - team option next year enhances value; may be best realistic option for starter available at deadline DEPENDS ON COST AND WHAT FA'S THE RED SOX PICK UP
Ogando - flip him for what you can get GONE
Breslow - probably should just get cut loose to give someone like Barnes, Hembree or Aro a chance GONE
Uehara - I love you Koji, but it's time to part ways NO ONE WILL GIVE BACK ENOUGH VALUE. STAYS IN THE PEN.
Napoli - same as Buchholz for 1B/DH options for contenders GONE (UNLESS PIXIE DUST IS FOR REAL)
Ross - see Breslow, except we can just option him down to AAA
I would suspect if the team continues to founder, maybe only 1-2 of the last category are still on the 40-man by September, and about half of the penultimate bucket will be gone, and then maybe 1 of the untradeable/unlikely bucket players will get moved. This isn't anything others have highlighted, just putting it on one post helped me recognize this roster doesn't have a ton of flexibility to clean house right now. Some of the retooling will simply have to come from the guys already here just playing better, or the team taking some big lumps for the next year or two. I DON'T THINK IT'S FOR A YEAR OR TWO...I THINK THEY RETOOL QUICKLY IN THE OFF SEASON, PARTICULARLY WITH A FA MARKET FLOODED WITH PITCHING AND SOME KIDS THAT MAY BE BLOCKED.