Since the Montreal series, this team should be in "all-in" mode. Dubas has tried, but with some reservation or internal debate/restrictions it would seem. I'd wager it works out if he strikes this year.
I didn't question his pickup of Foligno, I think it was a trade a knowledgeable GM makes and if not for Tavares injury 10 minutes in they probably beat the Habs. Anyone complaining of the price when he became injured is a revisionist, from ESPN to Canadian media the consensus was that the Leafs were big winners at TDL.
This team is deeper, more prepared, playing a more committed game Matthews in particular seems unconcerned about anything but winning. They also have cap space if Muzzin is out until at least the playoffs.
He has added Bunting, Gio and looks like a wizard for going for the goalie tandem which I thought made sense conceptually, but not with their injury history. I didn't like the risk, but Dubas, knock on wood, has hit a grand slam. They've been a great pair, and Murray oozes "I care about winning". Benn was a strong pickup and Timmins is no slouch.
YES, you go for it. Cup teams are built before the deadline but many are put over the edge at the deadline, no sport encourages this more than the NHL. Google is your friend if you don't believe me.
How far would I go? It all depends on the players.
Many believe we are designing a team similar to T.B, but I'd prefer more of a NJ Devils team from 1995-2003 (ironically built by Lamorello). Complete dominance on the defensive side and a HOF goalie, except this Leaf team has far more firepower. Those Devils had Gamers. Not always flashy but always highly competitive and able to beat very good teams they were supposed to lose to. Internally, Brodeur on out, they had no doubts.
I'd exchange a D Man for another physical rock. I'd exchange multiple forwards for depth and top tier, hard nosed talent. I'd trade prospects for value/term. You make a splash at the deadline and serve notice to the team, "we hear you, we believe in you and we are going for a Cup".
If for some reason MLSE won't allow him the freedom to do so, Dubas should pursue other options because this is the perfect scenario to bring in the Gamers for cost. No self respecting franchise would deny themselves the opportunity.
Win or lose, better to be the yang rather than the ying.