Leafs GM Kyle Dubas started his managing career scorching hot by signing the most sought-after free agent on the market this summer. Dubas stepped in to replace Luo Lamoriello, and made it known the #1 priority in the coming years was to keep their young core around. On Sportsnet’s31 Thoughts Podcast, he was asked about keeping Matthews, Marner and Nylander and his response was: “we can and we will”.

At the time, it seemed like he could do no wrong and the Leafs were poised to win five straight Stanley Cups. Then, people came down from the high that was John Tavares in blue and white realizing it might be tougher than it looks. Dubas’ time on cloud nine came to a screeching halt around the same time when talks with Nylander proved more troublesome than expected. The two weren’t able to come together on a deal until the December 1stdeadline causing the young forward to sit out 28 games. Obviously, Leafs management didn’t want Nylander to miss any time due to contract negotiation; it just happened. Dubas proved he was tough and didn’t budge realizing the bigger picture was more important. Nylander eventually came to his senses and signed the most talked about contract in the history of Toronto sports.

Dubas has another tough summer ahead of him as Matthews and Marner are up for contract extension. The difficulty that came from the negotiation with Nylander has given Leafs fans and media some understandable concern going forward. Nylander recognizes what lays ahead and gave some advice to Matthews and Marner on TSN’s That’s Hockeytelling them to “just get it done before the season starts.”

Dubas understands the pressure of the situation and he too wants to the deal done early “We do want to avoid a situation like we were just in [with Nylander], and we’re completely in control of that this time in that there is no excuse. I can’t say, ‘Well, I wasn’t doing this job a year ago.’ Our intention is that well before July 1 we have an agreement and both players are here long term.”

Hindsight is 20/20 and hopefully, everyone involved is able to act on Nylander’s advice. The Leafs have just over $23 (27 if the cap goes up) million in cap space for next season which might be a problem depending on the demands of Matthews and Marner. Matthews will absolutely get paid more than $10 million and if Marner’s set on it, he can get $10 million as well putting the team in a tough spot to fill out the rest of their roster.

Dubas isn’t concerned, with good reason, as both players have said they want to stay with the organization that drafted them. It shouldn’t be too difficult to keep these guys around since they are unrestricted free agents. That means once the Leafs send a qualifying offer, they’ll be able to match any offers that are given from other teams. “Our salary cap situation is set up that we could defend any of those threats with no worry at all, I spend zero percent of my time having any worry about that.” Dubas said about whether or not he’s worried about teams sending Marner and Matthews offer sheets. This is a very optimistic way of thinking for the young GM considering the hefty payroll ($40 M) they could develop around Marner, Matthews, Nylander and Tavares if someone gives Marner or Matthews an expensive offer sheet.

Presumably, the whole team has seen how they've been affected by Nylander sitting out for the first 28 games. They didn’t struggle at all without him but you can see how difficult it’s been inserting him back into the lineup. The team hasn’t totally looked the same with a 4-2 record since he’s been back. Their offence has been fine but on the other end they’ve given up 4+ goals in four of those games.

The core four of Marner, Matthews, Nylander and Tavares are the envy of every team in the NHL right now. You've got two of the top center-men in the league and two of the top young forwards in the league. Keeping them together is evidently important to everyone involved so I’m sure they won’t allow it to get to the point it got to with Nylander. With the experience, management will know how to deal with the situation and the players will understand the impact it will have on their season.