Leafs fans may not want to accept it, but in the playoffs Chiarot would be their #4D, behind Reilly, Muzzin, and Brodie. He would get way more ice time than Sandin, Holl, Dermott, Liljegren, etc.
I remember in a documentary the Leafs released after the playoffs, it showed one of the coaches talking to the players in the locker room, talking down on Montreal saying "they only play 4 defenseman". Well we all know how that turned out. Montreal rode 4 d-men (Weber, Edmundson, Petry, Chiarot) all the way to the finals. Romanov, Kulak, and Gustafsson were stapled to the bench after the 2nd period.
At the end of the day I don't see Toronto paying the price for Chiarot, but I have a feeling they trade a mid/late pick for Kulak to play 6th D once they miss out on any big fish.