If James doesn't resign with the Cavs it's a no-brainer that they should trade Love to get a younger star or draft picks. Portland would seem like a team that should be very interested in him. That team is build on their starting backcourt Lillard/McCollum with Nurkic and a couple of overpaid role players.
I don't like their game plan, it's primarily Lillard an McCollum taking turns on attacking the defense. The team lacks shooting and good perimeter defense. They need changes. In order to get something valuable you have to give up something. In this case it's a very easy choice to me: C.J. McCollum.
Cleveland could be interested in McCollum, he's 3 years younger than Love and is under contract for 3 years, to have a new star to build around. From a Portland's viewpoint you'd like to get rid of some of these bad contracts, but Cleveland doesn't have much good to offer either. However Smith and Clarkson might be better fits for Portland than Turner and Leonard.
Smith's defense may actually not be worse than McCollum and he just wants to be a catch&shoot player which may benefit Lillard's play. The loss of scoring power can be compensated by Clarkson. He was terrible during this play-offs but he actually played very well when he was with the Lakers. Ideal 6th man to bring necessary offense from the bench.
Turner has never blossomed in Portland, which was a bad signing and fit from the start. Trading him and Leonard (who rarely get meaningful minutes) would be great for Portland and on the other hand when starting a rebuild Smith (attitude) and Clarkson (selfish player) are not the type of players you want in your locker room if you're Cleveland.
So trade proposal:
To Portland: Kevin Love, J.R. Smith and Jordan Clarkson
To Cleveland: C.J. McCollum, Evan Turner and Meyers Leonard
Portland's possible new rotation
Lillard/Napier - Smith/Clarkson - Aminu/Harkless - Love/Swanigan - Nurkic/Collins
Houston Rockets roster:
G: Paul, Harden, Gordon, Knight, Rivers / F: Tucker, Green, Anthony, Ennis, Clark / B: Capela, Nene, Chriss, Hartenstein
Chicago Bulls roster:
G: LaVine, Dunn, Arcidiacono, Selden, Harrison / F: Parker, Markkanen, Hutchinson, Valentine, Blakeney / B: Carter, Lopez, Portis, Felicio