Likely could make it work with Trent Jr, Dick and a combination of Boucher, Porter Jr or Young along with a combination of alot of draft picks. Would be the ideal route for us if we get Dame and we obviously want to compete immediately. Mortgage the future in terms of picks but keep the core guys around and sign them to extensions and build from there. Have to think they would want OG, Barnes or Siakim with an extension in place but maybe maybe Masai and Webster can work their magic.
I think Portland would want Scottie Barnes and/or Dick.
As a casual Raptors fan with limited information, this is an outsiders perspective. Thinking out loud, from the Raptors' perspective, I believe it would make sense in the short term to keep OG over Barnes for spacing, if they want to "go for it". However, in the long term, giving up Barnes would be very costly and would hurt more than trading OG.
Regarding the Blazers, if they are giving up Dame, wouldn't they want to re-tool or rebuild? Therefore, they must desire a package resembling Barnes and Dick. However, I am unsure about how this would work with salaries because the salaries would be so out of whack.
Also, Dame's salary is so high, making 60 million and he's 33, so that must take a bit of a hit to his trade value.
Dick + picks + roster spares seems like not enough value for Portland. Could the salaries even work?
Dick + Barnes for a 33-year-old making 60 million seems like too much value going to Portland.
OG + Dick for Lillard seems like it wouldn't serve the Raptors "win now" ambitions.
It's challenging to envision a perfect and clear fit.