The timeline of events that led to Kyle Dubas’ firing from the Maple Leafs, plus the questions that remain

Maple Leafs President Brendan Shanahan sat at the podium inside Scotiabank Arena, and for 11 minutes, told his side of the story which led to the firing of Maple Leafs GM Kyle Dubas on Friday.

To say this was a bombshell of a press conference would still be an understatement nearly 24 hours later. Though as I read the quotes from Shanahan over and over again, I am still left thinking: “How did something like this get ruined so quickly?”

Below is the full timeline of events. I want to preface this by saying this is all on the account of Shanahan. Multiple reporters have reached out to Dubas for comment, but he’s elected to stay quiet, saying: “There will be a time and a place for that,” per TSN Insider Pierre LeBrun.

Summer of 2022: Shanahan told Dubas that he wouldn’t be offered a contract heading into the final year of his current deal. The hope from Shanahan was that, “after being judged for that full five years of his contract,” Dubas would be extended.

Mid-March 2023: Shanahan approached Dubas in his office at Ford Performance Centre. Shanahan said that “he had seen enough in his mind” to bring back Dubas going forward. Dubas took time to think about it and came back saying he was “comfortable” moving forward and that his agent would contact Shanahan.

End of regular season, start of playoffs: Shanahan felt, that after some good conversations with Dubas’ agent, he was in a position to present Dubas with “something that was pretty much a finished deal. That reflected what he wanted financially and what he wanted as a general manager — what was important to him.”

Conclusion of playoffs (Friday, April 12): Shanahan prefaced the importance of being ready to go (signing Dubas to an extension). Shanahan expressed to Dubas, the night the Maple Leafs were eliminated, that “I thought he’d done a good job.”

Saturday, April 13: “We (Dubas and Shanahan) communicated a little through text.” Shanahan said.

Sunday, April 14: Maple Leafs had a team photo. After that, the two (Dubas and Shanahan) spoke in Shanahan’s office. Dubas was presented with a contract and that, “He seemed pleased to receive that news so quickly,” said Shanahan. The two spoke about the team, how tough it’s been on Dubas’ family, and that maybe it wasn’t a good idea for Dubas to do media on Monday.

Dubas expressed that because his players and coach were doing it, he felt he should do. Shanahan respected those wishes.

Monday, April 15 (end-of-season media availability): After watching Dubas’ presser, where the Maple Leafs GM slightly opened the door to leaving, saying: “It’ll either be here or it’ll be taking time to recalibrate, reflect on the seasons here,” Shanahan felt differently.

At that moment, Shanahan said, “it was a very real possibility for me at that point that I would be needing to look somewhere else. And as part of my job, that is what I began to do while still hoping that Kyle and I could come to some sort of a resolution.”

Tuesday, April 16: “On Tuesday, Kyle and I did not meet privately.” Shanahan said.

Wednesday, April 17: “On Wednesday, we did meet privately and we did discuss this again for a long time. I had probably more questions than answers.” Shanahan said. The conversation didn’t give him clarity on whether Dubas would be back as Maple Leafs GM. It made him feel like Dubas might not want to be the GM.

“So, my focus, then again, continued toward the path of, “What do we look like next year with a different general manager?” Shanahan said.

Thursday, April 18: Shanahan says Dubas reached out and said that he’d speak with him, but as would his agent. Dubas’ agent contacted Shanahan and presented him with a new financial package. Shanahan says the conversation between he and Dubas’ agent was “brief.”

Dubas, later in the evening, according to Shanahan, sent him an email saying he did want to be the general manager of the Maple Leafs.

“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. “And as hard as it is to make a significant change to somebody that you’re close to, and that you’ve been working with for nine years, a gap had risen in the contract status, but nevertheless, the email that I received from Kyle, I just felt differently.

“And I felt that the long-term future of the Maple Leafs might have to change. And slept on that.”

Friday, April 19: “(I) woke up this morning, drove to Kyle’s office at Ford Performance Centre, and informed him that we were not going to be renewing his contract.” Shanahan said.

In a shocking turn of events — which began just eight days ago — Shanahan is left searching for a brand new GM while Dubas is looking down the barrel of a possible job with another club in the NHL.

The biggest question I have from all of this is, what was said during their conversation on Wednesday? It seemed as though there was still a possibility of Dubas returning even though he opened the door to exiting the organization before their meeting.

What I also don’t understand is, was the relationship that fractured where Dubas had to tell Shanahan via email that he wanted to remain as the Maple Leafs’ GM?

Jason Spezza, who was Dubas’ left-hand man this past season, reportedly tendered his resignation prior to Shanahan speaking with the media.

It’s also being reported by The Athletic’s James Mirtle that “many of Dubas’ other lieutenants would seem to be at risk. Assistant GMs Ryan Hardy, Darryl Metcalf and Hayley Wickenheiser were all close to Dubas and relatively short on front-office experience when promoted into their roles as part of an unorthodox front-office setup that had so many AGMs in different roles.”

While Assistant GM Brandon Pridham takes over the personnel discussions, Shanahan is left to pick up the pieces of the fragmented predicament he created.

Those shards include finding a new GM, and quickly. Plus, figuring out how they can retain both Auston Matthews and William Nylander, who are both soon to be entering the final year of their deals and can sign new contracts on July 1st.

If there’s anything that I know, it’s that this summer will be both very busy and stressful for the Maple Leafs’ President.