How the Kyle Dubas talks fell apart, and why both sides will regret it
Brendan Shanahan, President and Alternate Governor of the Toronto Maple Leafs speaks to the media during a press conference in Toronto on Friday, May 19, 2023. It was announced Friday that Kyle Dubas will not return as general manager of the Toronto Maple Leafs. Photo credit: Arlyn McAdorey/CP.

TORONTO – For all that was said and left unsaid about the Maple Leafs bombshell decision to walk away from Kyle Dubas, all you really need to know about how spectacularly everything unravelled is this:

Right up until the moment Brendan Shanahan walked into the general manager’s office and officially cut ties with him on Friday morning, Dubas hoped to continue on in his role.

And as recently as Wednesday, and maybe even Thursday, Shanahan was angling for the same outcome.

Nine years together flushed just like that. A sea-shifting change in direction for an organization already plunging into the unknown this summer. Quite possibly the beginning of the end for this Leafs era as we know it.

Truth be told, it’s an outcome both sides will almost certainly come to regret with the passing of time.

For the Leafs, there’s no possible way to stem the flow of Dubas loyalists now fleeing for the exits – an exodus that began with special assistant to the GM Jason Spezza tendering his resignation on Friday afternoon and will almost certainly continue with other staff and players.

As for Dubas, how and where will you ever recreate something like this?

The 37-year-old was instrumental in building almost every facet of what the Leafs are today from the ground up. His fingerprints were all over the roster, the farm system and the entire off-ice operation of an organization trying to bury the failures of multiple generations that came before.

They had a chance to get it done. No more.

Dubas clearly stretched his leverage to the limit during a brief round of negotiations, with his agent Chris Armstrong returning with a counter-proposal as recently as Thursday afternoon according to Shanahan, but who can blame him?

There is no external candidate who is unquestionably sharper or more qualified.

Let it be said here that Brad Treliving is now the favourite to replace him as Leafs GM because there are so few obvious options who meet Shanahan’s requirement that “having an experienced general manager would be an attractive quality.”

The others that fall into that category are Marc Bergevin, Peter Chiarelli, Chuck Fletcher, Ray Shero, Ron Hextall, Jim Benning and Dave Nonis.

The Leafs had a pretty damn good thing in Dubas, and he held one of hockey’s most attractive jobs thanks to them.

There was a good reason why Shanahan called him up to his Scotiabank Arena office last Sunday to formally present a contract offer. It wasn’t even 48 hours after the Florida Panthers shockingly eliminated the Leafs from a second-round series in five games, but the president didn’t want any potential doubts to take hold.

Dubas was working through his own process.

Ultimately, he got done in by the decision to speak publicly during the team’s end-of-season availability on Monday – “I had expressed to him that it was not my intention to talk to the media until I had something settled with him,” said Shanahan. “I expressed that I thought it was a good idea that maybe he didn’t either” – because it was there where Dubas first said he wasn’t sure about returning after learning how taxing things had been on his family. 

That set off alarm bells for Shanahan.

“There was a shift in my thinking at that moment,” said Shanahan. “A dramatic shift in my thinking.”

Still, they texted throughout Tuesday and met face-to-face for multiple hours on Wednesday. There was a chance to save the relationship. They could have used a marriage counsellor.

Distrust had crept into the equation, which explains why they couldn’t piece it all back together even when Dubas formally told his boss that it was his intention to stay roughly 17 hours before he was sent packing.

“At that point, if I’m being honest, I had gotten to a different place about how I felt about the future of the Toronto Maple Leafs and what was best,” said Shanahan. “A gap had risen within the contract status, but nevertheless the email that I received from Kyle [on Thursday night], I just felt differently and I felt that the long-term future of the Maple Leafs might have to change.”

Reached Friday, Dubas declined to share his own take on the events that led to his dismissal. He told me he didn’t feel it was the right time to discuss what had happened.

This was a seismic turn of events.

An earthquake had just occurred and multiple players that professed heartfelt allegiance to their general manager during Monday’s media session received early-morning calls from Shanahan to talk about his firing a couple days later.

Looking ahead, that’s bound to have ramifications.

As is the fact that Dubas was at the heart of everything that existed in Toronto. That includes the good and the bad, but it’s hard to imagine a newcomer getting a credible grip on what’s happening before Auston Matthews and William Nylander come due for extensions on July 1, and 12 other players have contract-related decisions made about them.

Make no mistake: There is no worse possible time to introduce a new GM to this complicated cap sheet, especially after Shanahan suggested that long-time AGM Brandon Pridham would only be overseeing the transition on an interim basis.

“There are a lot of people who are shocked and saddened today – and it would be a little strange if it wasn’t that way – but we also have a lot of people here that are coming back to work and doing their jobs and getting ready to do the things that they are paid to do,” said Shanahan.

It sounded like he was talking himself into it.

This is the first time it felt like the man behind the Shanaplan didn’t actually have a plan to work off.

NorthStar Bets editorial Insiders have no influence, direct or otherwise, over the setting of odds advertised on our platforms.