The verdict
This trade idea from O'Connor is likely to appeal more to the Milwaukee Bucks, who seemingly want to freshen up the roster with younger players while becoming more versatile defensively. Brown would be a perfect addition in that regard, and although Lopez would be a huge loss, there are ways for the Bucks to find a center who can replace the shooting and rebounding he brings to Milwaukee.
If the Milwaukee Bucks could pull this off without parting with any draft capital, it would be brilliant for them, but the Raptors' timeline suggests they could be looking for compensation or younger pieces to add to their current crop of young talent.
Both players being on expiring deals would put both teams in positions to try to cash in on their players before they become free agents in the summer of next year. Toronto is a couple of seasons away from really contending, and Lopez could be a nice defensive presence for them, but they could also flip him to add other assets.
Brown would give the Bucks great defensive versatility but also open up another offensive weapon they can use in the pick-and-roll game. Early on this season, the Milwaukee Bucks didn't have that point-of-attack defender, and Brown is that. He'd lighten the defensive load on Lillard, allowing him to focus more on his offensive game.
Overall, this trade is enticing for both teams. Milwaukee parts with a staple of their team over the years for a good, adaptable role player. Toronto gets a veteran on an expiring deal to potentially flip for more assets. Whether Toronto looks for draft compensation for Brown over this is the real question, but both front offices will be willing to explore making a deal around these two players.