Trailblazers: Jerami Grant is making far too much money for the role he will be playing for the Blazers this year and beyond. $30m+ annually for a bench wing is simply untenable for a team trying to be serious. Pat Williams can probably provide about 70% of Grant's utility for 56% of the cost. Moreover, there is always the chance that a change of scenery can shake loose some higher level play from Pat. Regardless, this is a financial decision for Portland.
Bulls: Nobody is really sure what the Bulls are trying to be in the short or long term. One thing that is obvious is that the Pat Williams experiment hasn't worked. Given they have the cap room to spare, upgrading from Pat might not be a bad idea. Say what you will about the Jerami Grant contract: he is the better basketball player. The fit is actually surprisingly clean for him in Chicago, too. You can slot him in the starting lineup either next to Okoro or in place of him. He can defend bigger wings on the ball, and has some scoring juice on top of being a capable spacer. It would be nice to see Grant on a team that values him, and Chicago will always love a guy that helps them inch towards the middle.