Brendan Shanahan’s curiously detailed firing of Kyle Dubas marks an ugly end of an era for the Maple Leafs

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The usual way of clipping a sports executive is the ‘Up in the Air’ model. Talk about how great he was, how much he meant to everyone and say you’re regretfully parting ways.

Years later, we may learn the ugly truth in someone’s memoir, but by then no one will care. Executives are designed to be forgotten.

Then there’s the way the Toronto Maple Leafs just did it. It’s not a good way, but it is a lot more interesting.

The Leafs parted ways with general manager Kyle Dubas on Friday morning. This wasn’t a huge surprise. After five years of on-ice mediocrity, Dubas was out of contract. There was no compelling reason to keep him.

Leafs president Brendan Shanahan did the usual presser to announce the split. That’s when things got weird.

Shanahan doesn’t talk much in public. When he does, he doesn’t say much. Few people in all of sport keep their thoughts under tighter wraps.

Until Friday.

Shanahan began with a minutely detailed, 10-minute chronological retelling of his effort to re-sign Dubas. It sounded more like the dissolution of a marriage than a failed contract negotiation.

According to Shanahan, it goes something like this. In March, Shanahan decides that he wants to give Dubas a new deal. Dubas tells him to call his agent and start working things out. Shanahan does that. The framework for a new deal is created. Dubas has no direct part in the making of it.

The night the Leafs get knocked out, on Friday, May 12, Shanahan tells Dubas he wants to get this thing done. He doesn’t hear anything about it from him over the weekend.

On Monday, against Shanahan’s advice, Dubas addresses the media. His presentation is erratic. He mentions several times how hard his job is on his family. At one point, he is near tears.

“For me to commit without having a fuller understanding of what this year took on [my family] is probably unfair of me to answer,” Dubas says.

Watching this happen on a screen, Shanahan starts to turn: “At that moment, there was a dramatical shift in my thinking.”

On Tuesday, the two men don’t talk. On Wednesday, they meet again. On Thursday, Dubas’s agent calls and “basically, a new financial package was presented to me.” On Thursday night, Dubas e-mails Shanahan. Now he’s sure. He definitely wants to be Leafs GM.

Shanahan, after reading that e-mail: “I had gotten to a different place about how I felt about the future of the Toronto Maple Leafs and what was best.”

On Friday morning, Shanahan wakes up, drives to the Leafs’ practice facility in west-end Toronto, goes into Dubas’s office and fires him.

A few hours later, he’s up on a podium at the Scotiabank Arena making sure that his version of events is the first one out.

I’m sure that high-profile staff negotiations are sometimes this disconnected and amateurish. I’m also sure you don’t usually hear about it in real time.

For a sports organization that is always going on about how collaborative and inclusive it is, this sounds like the least collaborative and inclusive dialogue in business history.

Why was an agent required as a cutout? Dubas does deals for a living. He can’t settle the basics of his own with the guy who is his rabbi in the NHL?

This is a team that keeps a vice lock on all communications. Did no one in the organization have any idea what Dubas intended to say to the media in his exit interview? Did no one bother to ask?

And why would Dubas sabotage the back-and-forth with an 11th-hour demand for more money after his own agent had already settled that issue?

What this sounds like is an organization in which people are constantly speaking, but never really talking to each other.

It also feels as though there is another side of this we have yet to hear. In Shanahan’s telling, Dubas comes off like a flake. Dubas has no choice but to fight back on that narrative. This thing could get ugly long before the memoir stage.

The immediate effect of this decision is to end an era.

If the Core Four define the Leafs as a team, Dubas was their Brian Epstein. He didn’t discover them, but he made them the centrepiece of the team.

Though that hasn’t worked, Dubas seemed inclined to stick with them. Will the next GM confine himself to adding small strokes to a painting made by someone else?

If not, things will have to start happening quickly.

The draft is in five weeks. Auston Matthews’s no-trade clause locks in the week after that. William Nylander needs a new deal. Someone is going to have to figure out how to get rid of Matt Murray. If you’re trading Mitch Marner, he’s not getting any more valuable than he is right now. And what about Sheldon Keefe?

Shanahan said the head coach’s future will be left to the next GM. That makes Keefe the walking dead. How many conversations do you want him involved in from now until whenever someone drives to his office on a Friday morning to have a little chat?

All of a sudden, just when a whole bunch of hockey decisions need to be made, no one’s in charge. If there is a plan, it’s not apparent.

That’s the real era that’s ending – the one in which everyone believed the Leafs had finally become a fully modernized, state-of-the-art hockey machine. For the nine years Shanahan has been in Toronto, you always got the sense the Leafs had a vision.

Even when their ideas didn’t work out, you did at least believe there were ideas in the first place. That this was one of those organizations playing chess, not checkers.

On Friday, that impression came apart. The Leafs no longer look like a well-run team that’s this close to breaking through. They look like every other dysfunctional business, the sort where nobody knows what anyone else is really thinking and where the work just sort of does itself. Until one day it doesn’t.