On Portland, I honestly don't think they'd do as bad on this deal as some see it. Yes, they would get rid of a bunch of their role players in the process, but you have to look at what they'd get back now and what they'd be getting in the future. Let me 'splain....
While I like Jarrett Jack, he has been fairly solid but mostly unspectacular for this team. That lands most young PGs somewhere between $5-7M a year in this league nowadays. And if I asked, would you rather have one or two guys making $5-7M a piece (like they have in Seattle) or one kid with great potential making enough to be your no-kidding starting PG, I think most would agree that the latter is the preferred choice.
Then you have to look at the other pieces they would give up. Frye's role on this team was decided when Aldridge stepped out and had a monster year....he needs a change of scenery. And Outlaw, while he improved his jumpshot out to 18ft, is still a superskinny non-rebounding combo forward with his main skillset still being his athleticism.
Now you have to look at what's coming to the Blazers in the future. They've gpt Oden coming back next year to an already-crowded frontcourt...keep in mind they still have McRoberts on the bench and Joel Freeland overseas. Then in the backcourt and on the wings they have Sergio Rodriguez, an emerging Martell Webster, and Rudy Fernandez who will most likely be here next year.
Bottom line: They have to make some serious roster decisions at one point or another and if they can get back a potential star PG in the process versus the PG-by-committee approach, I think they do well.