You do it if it's buy low, and I don't think it's crazy to include Rozier for Winslow, even think right now Rozier is a more useful player to us.
Rozier is barely a backup PG, and on offense he clearly plays SG. Moving Smart for Winslow creates that problem, as Smart is our primary backup PG.
Brad would get the most out of Winslow, but I doubt it happens. Ainge and Riley just don't work well together.