When would you make these trades? The reason I ask is if it looks like Boston isn't going to make the post season, even after trading for aldridge, and there are no protections on Boston's own pick, then Portland might very well do the trade on the off chance that Boston hits in the lottery.
If Toronto is out of the playoffs I could see them just trying to sell of Gay, but I think they would want some sort of value and not just salary relief.
All of that said, I'm not entirely sure I would do this unless I was positive I could do both trades. One alone isn't worth it, but both of them would give Boston a pretty solid team, especially if Boston was able to hang onto Sully, Fav, and Oly.