From the Raptors perspective, this trade doesn’t make too much sense, but it makes a lot of sense from the Bucks perspective.

Middleton is on the decline, and you would get back two guys that have championship experience (Boucher with Toronto, and Brown with Denver). Also Brown would be a great backcourt mate for Dame, as Brown is an elite defender on and off the ball, and if he’s shooting the ball anything like he was with Denver, that’d be huge for Milwaukee. Boucher’s trade value is at an all-time low as he just had his worst season since his second season in the league (when he was only playing about 6 minutes per game). Boucher would be good depth to add to this Milwaukee team.

Like I said before, this deal doesn’t make much sense for the Raptors, but Middleton could be a good mentor for rising stars like Scottie Barnes and RJ Barrett. Middleton who’s a 3-time All Star and an NBA Champion could provide valuable mentorship to this young Raptors squad, and who knows they could maybe sneak into the playoffs, as it was injuries that hurt them last season.