I completely agree with you, but don't know how to get a deal done.
Presumably, Portland wants salary relief (so they can sign big name free agents). So they will want to deal with a team with room, like Memphis or OKC. The question is, is it possible for Boston to get in on a three way? For example, send Scal to Memphis, Memphis sends a trade exemption to Portland, Portland sends Outlaw to Boston? Obviously Portland will want a little more than salary relief in return, and Memphis will need to be remunerated in some way. Maybe Boston sends Scal+Walker+future 2nd rounder to Memphis and Boston also sends a protected future 1st rounder to Portland....
Not only would such a deal net us a very solid backup at the wing, but it would help Portland sign Hedo or whoever they are going after, and I say better to send the FA to a team in the West than to a team in the East...
Now remember that reported deal which would have sent Scal+Tony+Walker to Memphis on draft night for a 2nd rounder? If the Cs had been able to pull that off, then they would be able to use the resulting exemption created to trade directly with Portland for Outlaw... (darn you Chris Wallace!)