Beyond Headlines: What we learned about Dubas during Nylander saga

Ron MacLean, Nick Kypreos, Chris Johnston and Elliotte Friedman tackle all the top news from around the NHL.

‘Beyond Headlines’ is a deeper dive into some of the stories — and even some that weren’t — discussed each week on Hockey Night in Canada’s ‘Headlines’ segment.

This would not have been possible as recently as 2013.

Good luck trying to conduct an intercontinental contract negotiation against a hard deadline in the days when the NHL required documents to be sent in for registration by fax. Fortunately, Kyle Dubas and agent Lewis Gross live in the era of electronic filing and could therefore use absolutely every last minute available to them before Saturday’s Group 2 signing period closed.

Their negotiation on William Nylander’s second contract signals a shift in the way NHL business can be done because of the personalities at the heart of the deal.

In Nylander you had a 22-year-old willing to stretch this process to the absolute limit, risking a valuable season of his preciously short career. In Dubas you had a man just 10 years Nylander’s elder, who refused to let things get overly contentious even as frustration built on both sides of the table while everyone flirted with disaster.

Not only did the Toronto Maple Leafs general manager travel to Switzerland at one point to sit down face-to-face with Nylander, he kept an open dialogue through texts and phone calls.

This was not a negotiation built on threats and false deadlines and F-you’s.


Nylander continued to wear Leafs gear while skating with AIK’s under-20 team in Stockholm and frequently liked Instagram posts from the official Leafs account. Dubas didn’t spring a bunch of trade leaks even while performing due diligence and gauging the player’s value.

One team who called Toronto’s front office with an offer in the last few days was told that they felt good about the odds of getting something done with Nylander and wouldn’t be putting him on the block.

Honest and straightforward. No games.

When it came time to make the deal, Dubas and assistants Brandon Pridham and Laurence Gilman got creative with Nylander and Gross, his representative.

There has never been a contract structured quite like it in NHL history.

The Leafs own tons of salary cap space this season and will start to feel the squeeze in 2019-20, so they came up with a way to pay Nylander heavy right away — to the tune of more than $17 million by July 1, making him whole and then some for the days missed because of the impasse — while gaming the cap system and keeping his AAV to $6.96 million for the final five years of the deal.

They also built in some lockout protection with annual signing bonuses of $3.5-million starting in 2020. They added a 10-team trade list in 2023-24, the only year he was eligible to receive such protection.

They basically guaranteed Nylander would walk away feeling good about the contract while keeping him within a range where they believe Auston Matthews and Mitch Marner can still be signed without breaking up the band.

Now, it must be noted that there are no shortage of whispers out there saying that Dubas and Co. caved on this deal. That they merely gave Nylander everything he wanted rather than crushing him at the 11th hour, leaving the Leafs vulnerable heading into the Matthews and Marner negotiations.

I would argue that he showed strength and ingenuity under the intense spotlight of a negotiation that spanned months. He worked towards an end capable of satisfying both club and player even though it meant stretching a little beyond his comfort zone with the final cap number. He did it his own way.

Dubas will ultimately be judged on keeping his package of stars; whether he can make good on the “we can and we will” promise he made to Elliotte Friedman and Jeff Marek on the 31 Thoughts podcast. But consider what Matthews and Marner learned about their GM during the Nylander negotiations: That he’s reasonable and business-like even when talks get tough, and he’s sincere in his intentions about finding a way to make things work for all of the core pieces in Toronto.

Dubas could have proven a point by letting Nylander sit out a season at a time when this organization finally seems capable of challenging for the Stanley Cup. He could have gone into the final hour of talks and chosen the nuclear option.

Instead, he showed a dealmaker’s touch and gave his players another reason to believe that they’ve got the right man calling the shots above them.


They are coming with a group that will run 30 deep at the NHL’s Board of Governors meeting in Sea Island, Ga.

They are promising to bring along a surprise guest or two.

This is a bloody big deal for the NHL Seattle folks who are due to take ownership of the league’s 32nd franchise on Tuesday morning — needing three-quarters support from existing owners in a vote that’s more of a procedural formality than anything.

Then, once the deed is done, they’re heading straight back across the continent for a ground-breaking ceremony at KeyArena later in the week, kicking off a major demolition/rebuild project that will determine if the team starts play in 2020 or 2021.

The fact shovels are hitting the ground immediately underscores the city’s commitment to starting as soon as possible. What kind of signals the league sends out during the BOG bears watching. There’s already been some backroom discussion about opening Seattle’s inaugural season with a bunch of road games in case the arena isn’t finished, but the NHL isn’t believed to be in favour of that option.

There are also concerns about potential construction delays.

So as Seattle finally gets its team, we ask: Just when is the party starting?


With Chuck Fletcher the runaway leader in the race to be named Philadelphia Flyers GM, there is an expectation that he will need to hit the ground running.

Paul Holmgren and the team’s Comcast ownership group made it clear that a major part of Ron Hextall’s dismissal was due to a perceived lack of action. So not only will Fletcher have to make a determination on the future of head coach Dave Hakstol if offered the job, he’ll be expected to dive into the trade market before the Feb. 25 deadline passes.

This alone makes Philadelphia a team to watch closely in the months ahead.

The Flyers boast a strong prospect pool and have plenty of cap space, which is a testament to some of the good things that happened on Hextall’s watch. He’s left his successor a lot to work with.

Even though a new GM typically likes to take some time to survey his environment before making big decisions, that doesn’t seem like an option for Fletcher in Philadelphia.

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Lost among the talk of Erik Karlsson’s return to Ottawa, and Erik Karlsson’s uncharacteristically slow start, is what is to become of Erik Karlsson?

It doesn’t sound as though there have been any serious talks about an extension with the San Jose Sharks yet and that make some sense. They are still getting used to him, he is finding his way with them, and the team has struggled out of the gate.

But it won’t be long before the sides need to start figuring out if they might have a long-term fit together, and if not, what that might mean.

It seems highly unlikely that the two-time Norris Trophy winner would be traded again before the Feb. 25 deadline, but if he decides to test unrestricted free agency it could make for an awfully interesting July 1.


The outrage was predictable, and understandable, because of the name attached to the match penalty. The reaction should be a cost-free reminder to Tom Wilson that every check he throws for the forseeable future will be scrutinized down to the nanosecond.

Wilson escaped supplemental discipline for Friday’s late hit on Brett Seney because the NHL’s department of player safety employs a different standard than the court of public opinion — judging the infraction on its own merits before weighing the track record of the player who committed it.

The Washington Capitals agitator is fortunate because he certainly hasn’t earned the benefit of the doubt. No player has put himself on the DoPS radar as often as Wilson over the last 15 months.

For context, a refresher:

• Sept. 22, 2017 — Wilson delivers a late, predatory hit on Robert Thomas, earning a suspension of two pre-season games.

• Oct. 1, 2017 — Wilson boards Samuel Blais from behind, earning a four-game suspension.

• Oct. 29, 2017 — DoPS senior vice-president George Parros meets Wilson in Calgary to review video of checks that have raised concern in his department.

• May 1, 2018 — Wilson delivers an illegal check to the head of Zach Aston-Reese, earning a suspension of three playoff games.

• June 2018 — Parros phones Wilson after a late hit on Jonathan Marchessault during Game 1 of the Stanley Cup final, warning him to make better decisions in the timing and selection of his checks.

• August 2018 — Parros meets Wilson in Toronto to review more video, including checks to Alexander Wennberg (first round), Brian Dumoulin (second round) and Marchessault during the playoffs.

• Sept. 30, 2018 — Wilson delivers an illegal check to the head of Oskar Sundqvist, earning a 14-game suspension after appeals.

• Nov. 30, 2018 — Wilson delivers a late hit on Seney, earning a match penalty.

What spared Wilson on the Seney incident is a lack of head contact and predatory intent. There have been approximately 20 interference suspensions since the DoPS was formed and each has included one or both of those elements.

He didn’t change his path or lean into the hit, but he also didn’t avoid contact with a defenceless player. He skated up to the line but didn’t quite cross it.

For Wilson, that’s a dangerous choice to make: Everyone is watching closely.

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