Dubas can sign him before July 1st to avoid exposing him
its all business and Dubas knows that. Is Toronto gonna be pissed and trade Matthews?
They aren't getting as good of a return in a trade as they are in an offer sheet. Four unprotected first round picks from a team who is either bad enough or early enough in their rebuild to have the 13+ million to offer sheet Matthews has the upside to be a dynasty building acquisition for a team in Toronto's position that would still have a top level center in Tavares, an elite forward in Marner, and two very good forwards in Nylander and Kadri.
The benefit of a trade would be that at least part of what they get back will be an established player, so they won't invite a situation where 5+ years down the line they get really unlucky and none of the 4 first round picks they got pan out leading to them having lost Matthews for nothing.
If he won't sign, I think they have to wait for the offer sheet. It lets them fall on their own sword and portray Matthews as the villain. They get the high upside return between four unprotected 1sts and the huge amount of cap space freed up.
I wouldn't say the same thing under the old lottery system, but the new system has changed things. Giving a team an unprotected 1st for one season can be frightening....four seasons in a row for a playoff bubble team means there's a really good chance at least one of those picks is going to be a star.