How the Kyle Dubas, Brendan Shanahan negotiation fell to pieces

Toronto Maple Leafs president Brendan Shanahan breaks down the timeline that lead to general manager Kyle Dubas's departure, sharing that he was working on an extension with Dubas for several months before talks broke down.

TORONTO — An emotional and honest press conference.

A request for more money than anticipated.

An email expressing a desire that arrived too late.

These are the levers that, as president Brendan Shanahan presented in a measured press conference Friday, pulled Kyle Dubas away from the Toronto Maple Leafs after nine years of heart-on-sleeve service, the final five as general manager.

“This was ultimately my decision,” Shanahan asserted.

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Here, according to Shanahan, is how he arrived at the decision to not renew Dubas’s contract Friday and begin an urgent search to hire the next general manager of the Maple Leafs as soon as possible.

Flash back to the summer of 2022, Dubas having guided the group to its sixth consecutive opening-round exit, the fourth under the young executive’s tenure. 

Shanahan walked into Dubas’s office at Ford Performance Centre and informed him that he would not be receiving a contract extension. Dubas would be judged on the full five years of his original deal. 

He took the news like a pro and reiterated his comfort with letting his work speak for itself at training camp.

Evaluating Dubas’s work in 2022-23, be it his off-season moves, his management style or his trade-deadline overhaul to the supporting cast, Shanahan liked what he saw.

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“I think Kyle did an excellent job,” Shanahan said. “He made some very good moves, and I thought he had prepared the team to the best of his ability as any GM can do. After the trade deadline, there’s not as much for a GM to do.”

Dubas had accomplished enough in his boss’s eyes at that point to merit a raise. So, Shanahan approached the GM in mid-March with an offer to begin contract talks.

Dubas came back a week later and connected Shanahan to his agent, Chris Armstrong. Dubas told Shanahan that he didn’t want his negotiations to be a distraction down the stretch.

Shanahan believed there was progress being made on a deal, via Dubas’s agent, that when the season ended or between playoff rounds, the sides could come to agreement.

Shanahan says he wanted to lock up Dubas early. The president even mentioned the extension last Friday night, fresh off the disappointment of the Leafs’ Game 5 elimination at home to the Florida Panthers.

The two men exchanged texts Saturday.

On Sunday, the Maple Leafs gathered at the rink for a team photograph. Afterward, Dubas went into Shanahan’s office, where the two spoke for a couple hours and the boss presented his employee with the framework of a contract he believed would get everyone’s sign-off.

During that meeting, Dubas mentioned how difficult his high-profile job had been on his family.

“It’s the job we choose. It’s the sport we choose. We’re very fortunate to be in it, but it does not come without a toll on the families,” Shanahan said. “I completely acknowledge that. And we talked a little bit about that.”

Shanahan told Dubas he did not wish to speak publicly until the deal was done and suggested Dubas, too, avoid the microphones at Monday’s locker cleanout and season-ending press conference.

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“Kyle said he really wanted to talk to the media, and I respected that,” Shanahan said.

What Dubas said — and how he said it — at Monday’s podium created “a dramatical shift in my thinking,” as Shanahan drove home that night: “As Kyle expressed, he might not want to be our GM. And I have to take that very seriously.”

Still, Shanahan maintains he was hoping for a resolution. The men didn’t speak Tuesday. They met privately Wednesday for a long discussion that left Shanahan with more questions than answers. 

“I did not have clarity,” Shanahan said.

“My focus then, again, continued toward the path of: What do we look like next year with a different general manager?”

On Thursday, Dubas’s agent presented a new financial package to Shanahan. The gap had widened in favour of Dubas. Around dinnertime, Shanahan received an email from Dubas saying, yes, he did indeed want to manage the Maple Leafs.

Too late. Shanahan’s mind had made the shift.

“I wouldn’t characterize it as breaking down over money,” Shanahan said. 

“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.”

The president slept on his final decision, woke up Friday morning, drove to Ford Performance Centre, walked into Dubas’s office, and let him go.

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The Marlies coaching staff — head coach Greg Moore and assistants A.J. MacLean and John Snowden — was also left unrenewed.

Jason Spezza, special assistant to Dubas, tendered his resignation.

Shanahan’s focus immediately shifts to pursuing candidates to be Dubas’s successor.

And with a draft next month, free agency on its heels, and Auston Matthews and Mitch Marner’s no-movement clauses kicking in July 1, time is ticking.

The president says he will lean heavily on Brandon Pridham, Dubas’s assistant GM, during this transition period and will remain open-minded when considering résumés in a hunt for “new ideas and new thoughts.”

In the interim, head coach Sheldon Keefe — Dubas’s handpicked bench boss — twists in the wind with so many expiring player contracts.

“Some of those decisions have to be the responsibility of the new general manager,” Shanahan said. “Certainly, having an experienced general manager would be an attractive quality,”

Who is that? When will they be hired? How will they handle a Matthews deal that could make him the highest-paid player in the sport?

One big decision has been made, only to unravel more in its wake.

“Without making any promises, we will look at everything in the organization and try to make decisions that will make us better. And that might be not on the timeline that everybody wants,” Shanahan said. “The goal wasn’t just to get past the first round and everything gets easier.

“There is no nice summer or finish line just for having a partial success.”

And no contract extension either, apparently.

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