The only way Dubas wins was by going down swinging and show he wasn't a push over in contract negotiations. To do that he had to do what was in the Leafs best interest and not his own personal interest. He didn't cave early and fought hard at the plate until the bitter end..He didn't let his own ego get in the way and willingly go over the cliff with Willy which helped no one.
Getting Nylander signed is a big win for him, because it helps the team he manages get stronger and more Cup competitive the #1 goal here. The teams success on the ice is how the performance of the GM is measured. The more the Leafs win the better Dubas looks in the big picture, and if it results in a Cup win than Kyle gets a great big STAR for a job well done.
He wins because he also used MLSE financial wherewithal to front-load the deal with signing bonuses so that 40% of Nylander contract including $17.7 mil is paid in full on July 1st 2019.. That makes the Nylander contract very movable in the future should Leafs run into cap issues and need to make sacrifices. In fact it appears to be created by Dubas for exactly that purpose which again helps the team manage the cap going forward via flexibility and options via its structure.
Holding out until the last day is also a win for Dubas because of the way the CBA handles RFA signings for holdouts.. .Leafs are taking a massive
$10,277,778 mil cap hit in year #1 when they have lots of cap space to absorb it, and benefit in years 2-6 with a lower AAV when they need the space most.
So Dubas lost the war and struck out on his attempt to get Nylander at a cap friendly deal because the deck was stacked against him, but he did come away winning some important smaller battles along the way that puts the Leafs into a better winning position going forward.
Those battles that Dubas did win did not come at the expense of Nylander however, and this contract battle, so those are things Gross/Nylander would gladly give him as few foul tip balls on his way going down swinging to keep my baseball analogy going.
In the end it was a Win all around as Leafs Win (Leafs got stronger) -- Nylander Wins (got his $$ he wanted) -- Leafs Nation Wins (Willy is back in the fold to cheer on) -- Dubas wins as he did his job and did what was best for everyone involved.