Matthews has struggled in the playoffs, but he's a top-level stud, he plays C, and he has size. If Toronto wanted K. Miller, Lafreniere, Garand, and 12th overall I would do it. That's a haul for Toronto, I think. They get a top 4 dman, a former # 1 pick overall, a future # 1 goalie (which they need badly), and the 12th pick.
Add up Miller and Lafreniere you get $12.5M, I'm assuming Miller gets $5M +/-. Matthews makes $13.25M for three more seasons, so Toronto would clear some cap space, and if they let Tavares go, they can afford to keep Marner. Toronto either let's Marner walk for nothing, or they have to deal Matthews or Nylander, get assets back, and re-sign Marner. Letting Marner walk for nothing is not a smart move for Toronto. If I was Toronto I would absolutely 100% trade Matthews or Nylander for assets, then re-sign Marner.
As I said whether it's trading for Matthews, or something else bold, this is what Drury should be focused on. Signing Bennett, while a good player, is not changing the core and tone here. Drury needs to be bold, and a trade for Matthews is just that. It doesn't need to be Matthews, but Drury should be thinking in creative bold ways. That's my main point.