Celtics: B I am a huge Anfrenee Simons fan, and getting an expiring contract for Jrue that you could flip for more draft capital or keep and let walk in a year to clear up cap space is a positive for the Celtics. The thing that bumps this grade down for me is that I'm skeptical that there weren't better offers out there and that waiting it out might have seen a better deal emerge than a player who I will be shocked if he is still in Boston by the time Tatum is healthy

Blazers: A- With a leap from Scoot Henderson next year (which isn't guaranteed), the Blazers could make some noise in the West. Simons was getting in the way of Scoot and Sharpe's development, so getting a player in Holiday who can play alongside both of them while providing a steadying veteran presence, while only giving up two seconds, is a pretty solid deal for Portland. My only issue with this deal is that you now have both Holiday and Grant on multi-year deals, which could get problematic once some of your younger players come up for extensions.