We've seen many iterations of the possible offers the Celtics are making (allegedly) for Kevin Love and most of them include cap filler, one of our young guys and some picks.
Putting aside whether you would want Love or some other star for a minute, let's evaluate what is most important to keep in any blockbuster trade proposal. Likely, at least in the Love situation, the other team would dictate which would get included over the other, but it is always helpful to self evaluate and know what you value most.
Best case scenario he is a poor man's Kevin Love and maybe not all that poor. The thing for me with Sully is that, to a man, everyone I. The celtic's organization agrees he's been playing out of position at center and he is going to lose weight and play power forward this year. To me, this means that we are far more likely to see a breakout year from him as he will be playing as someone with his body type should. Worst case, he sticks pretty much where he is, never masters the three ball and keeps shooting it.
Best case scenario he is a poor man's Dirk. I think most would agree that he has less of a shot at approaching Dirk levels than Sully does at approaching Love levels. Still, he had a very good second half of his rookie season after a middling first half and he showed flashes on both ends of the floor. Worst case scenario he gets pushed around on the floor too much and is never at home inside or on the perimeter.
Celtics' Draft Picks:
If we're trading for a star, our draft picks matter much less. Of course protections should be negotiated in case of something very bad. Nobody wants to give the Pistons Carmelo Anthony because of a stupid trade a long time ago ... Oh wait, they wasted the pick on Darko. Still.
The Celtics' picks this year are very valuable in a pretty talented draft. The only problem with # 6 is that it seems to be the first pick of the "next tier".
The Clippers' Pick:
Despite what some hopeful over the Clippers demise in their fluid ownership situation may think, this is virtually guaranteed to be in the mid 20's next year and should be valued accordingly. This is not much after where we got Sully or Olynyk, but I think most would agree they'd rather have 2 players who worked out well so far drafted in that range than the possibility of getting those players if they get lucky.
The Nets Picks:
These picks are truly lottery tickets. They are unprotected and could be awesome if the Nets implode or could be late 1st rounders if not.
I would value these players and picks as follows from most valuable to least:
Nets 2018 Pick
Nets 2016 Pick
Celtics 2014 Pick #6
Celtics 2014 Pick #17
Clippers 2015 Pick
Celtics Future Picks
Under that logic, if I were Danny Ainge and I could keep either of the two players by tossing in another pick that is below them on my list, I do so. Maybe with the exception of Jared and the Nets 2014 pick, those are close for me. Ideally, I'd like to keep either KO or Sully, but not both of them (especially if bringing in Love), so I suppose there could be circumstances where I'd rather trade one of them than a pick that I see as a lessor asset. I think, in that situation, I would still trade the pick, assuming I could later trade one of the players for something better.