If you trade Brown for Bridges, which is never going to happen, Bridges can't settle into a #3/4 role. He needs to be the #2, so all the complaining about Jaylen's ability to be a playmaker will just be complaints about Bridges inability to be a playmaker.
IMO, the move that must be made this offseason is Marcus Smart. I don't think there will be a great return for him, but IMO, he's the piece that doesn't fit, because he's a zero on offense, and teams don't have to respect him at all on the perimeter.
If I had 3 wishes, I'd do a straight up Marcus for Vanvleet trade right now. Marcus is losing a step on defense, so we aren't giving up as much there was we were before, and VanVleet is coming off a down shooting year, but his assists are climbing. That, IMO, is the type of move I'd love to see Brad pull off, but we need a guy who can knock down a shot and keep defenses a little honest.