A trade between Portland and Toronto makes so much sense, as both are caught between rebuilding and competing. They each have half a team geared towards rebuilding and half towards competing. The teams should work out one of these two trades:
Trade 1: Portland competes
Portland gets: Siakam, OG
Toronto gets: Henderson, Kris Murray, Simons, Nurkic
Trade 2: Portland rebuilds
Portland gets: Barnes, Dick, Boucher, Trent Jr.
Toronto gets: Lillard
You could mess around with some draft picks / salary filler in either trade, but the point is that both teams emerge with a clear direction and better personnel to execute that vision than they currently have.
I know Toronto is stuck on sending out Barnes, but look at the five ROY after Lillard (Carter Williams, Wiggins, Towns, Brogdon and Simmons). There isn't a player in the bunch who is a 1a option on a playoff team. Teams tend to overvalue their ROY candidates. Besides if they are really sold on Barnes, then keep him and we will send young players to compliment him if they send out their veterans.
I know Dame said he wants out, but if you offered him a starting five of Matisse, Grant, OG and Siakam that a better supporting cast than he's going to get in Miami.