The twittersphere is awash with word that a first round pick can get a team Jamal Crawford. Boston desperately needs scoring, and that's one thing that Crawford can do. He's a tweener guard, but could be the Cs Jason Terry type.
If Ainge is convinced that these old geezers on the Cs have another deep playoff run in them, he's got to find a paint presence and some scoring in the next couple of weeks. Crawford has a player's option next year for $5m, so he might be only a rental, but since over half the later first round picks don't ever do much in the league, it might be worth the gamble. The Clippers pic will be later first round.
Trade JO for Crawford, sign a bought out Chris Kamen, and make one more run at a title.
There is no single 'answer'.
If we make the trade, what is most likely is we will still disappoint and then we will say "why did we mortgage our future for this" or the more stubborn will say "why didn't we also do this other move that would have been the 'answer'."
The team isn't good enough to make 'final piece' moves. Any move we do has to provide value for next year and the year after.