The main reason I thought Hedo would have been a good fit in Portland is his ability to run the side pick-and-roll. He ran it beautifully with Dwight Howard in Orlando, and I really thought it would have have been a big help to Greg Oden's offensive game.
In that respect, I also thought Hedo would have been a much better fit in Portland than in Toronto. Toronto lacks a post up center. So, Hedo becomes just another weak defending, poor rebounding perimeter player on a team that's loaded with them.
He would have added something we don't have in Portland. In Toronto, he's redundant.
Also, the Blazers are much closer to contending than Toronto. So, it makes more sense to overpay a 30-year old veteran with a lot of post season experience. Toronto isn't close to being a contender, even with all their of season moves. So, if Bosh stays, they probably won't ever get past the first round. If he leaves, they have a lottery team with multiple huge, long term contracts (Calderon, Bargnani and Hedo) tied up in guys who don't play defense or rebound the ball. Signing Hedo, and resigning Bargnani to that ridiculous extension, both smack of desperation by Colangelo. He had to do something to keep his job, and try to convince Bosh to stay, after last year's 33-win disaster of a season. In the process, I think he has doomed that team to years of mediocrity - at best. More like a couple years of mediocrity followed by another 3+ of total suckage.
BNM