So Toronto get Simons, A young guy who can play like Dame (what a surprise) and is a great two way guard. Simons has All star potential and has showed that when he gets to star in a role when Dame was injured. Kris Murray is a nice and underrated player who dropped late in the first round. Kris is Keegans brother and he can always help with his game. And also got Little in the trade as well.
For Portland, the main thing is Dame stays on the team for them. If they get a guy like Siakam they may convince Dame to stay for one more year to complete what he started (2014-17 Trail Blazers, Damn you Warriors), Siakam bring Defence which they don’t have at the forward spot right now and they only lose Simons from it and get Scoot as a replacement for him. Overall I think it’s a 50/50 trade and both teams win for the now