“You just saw how ruthless Brendan Shanahan can be.”

That was one view from inside the Maple Leafs house on Friday evening, hours after the team president walked away from his GM of five years, Kyle Dubas, and delivered an oddly detailed, day-by-day, almost hour-by-hour recount of a failed negotiation on a contract extension in a short press conference.

Less than a week after the Leafs were eliminated by the Florida Panthers in the NHL playoffs, the front office has effectively been pulled apart, first with the Dubas decision and then with the news that all three Marlies coaches were fired and special assistant to the GM Jason Spezza had resigned.

It’s also clear that more dismissals and resignations are coming in the near future.

Perhaps a lot of them.

As reported previously in the aftermath of the Leafs elimination, Shanahan and Dubas had been at odds for a while. On Friday, more details emerged on that front. Multiple sources close to the team said that Shanahan had blocked transactions that Dubas wanted to make at key points in the past several seasons, creating frustration in parts of the management group. Shanahan had also at times dictated certain moves he wanted made that Dubas didn’t agree with.

The president, as per his place in the hierarchy, typically won out in those battles. And, in some cases, the moves that weren’t made could have improved the Leafs’ ability to advance further in the playoffs.

With Kyle Dubas out as GM, the Maple Leafs have willingly plunged into chaos and uncertainty: https://t.co/2xsa1xCR4i

— Jonas Siegel (@jonassiegel) May 20, 2023

Some of those disagreements likely contributed to the disarray Monday, when Dubas delivered an emotionally charged, unusual season-ending press conference during which he declined to commit to coming back as GM.

That press conference concerned Shanahan greatly, as it went off script from the talks they had had to date. He had spent months vouching for Dubas to Maple Leaf Sports & Entertainment’s board and had finally won approval to negotiate a long-awaited contract extension, something that some members of the three-pronged ownership group had denied the previous year.

The friction in the Leafs front office and the relationship between the two men was still a factor, however, and Dubas’ desire for greater autonomy from Shanahan is believed to have been one of the untold reasons for how things ultimately played out.

Now those remaining in the organization are taking sides. Some on the Dubas side are preparing, like Spezza, to leave. Others are hopeful of moving up in the new world order.

It is, in short, a bit of a mess.

Others connected to the team, however, are simply disappointed that what had been a successful partnership between Shanahan and Dubas for nine years fell apart so quickly and so publicly.

Everyone knew all was not well. But few expected it to implode like this, right before the finish line.

“Really tough on everyone,” said one team source. “Not feeling great about the whole thing today. It should have ended very differently.”

It should have ended, they say, with Dubas remaining the Leafs GM.

That it didn’t will be a topic debated in NHL circles for years to come.

Only those who were in the boardroom know for sure, but one of the things that is believed to have been discussed during Dubas’ first meeting about his contractual status with Shanahan and ownership last Sunday was coach Sheldon Keefe’s future.

It’s likely Dubas was told then that Keefe would (or should) be a casualty during an offseason that all involved agreed required significant change.

There is also a view in the organization that players have become too comfortable, which will likely feed into whatever organizational decisions are made this summer. Part of what was at issue with the board was whether Dubas was prepared to make those hard decisions, such as firing a coach he was very close with and trading players he had backed ever since they entered the league up to seven seasons ago.

Was that part of what went into Dubas going off script on Monday? Perhaps. He declined to comment when contacted by The Athletic on Friday, but others in the organization believe whatever happened Sunday weighed heavily on him, especially in the emotional 48 hours after another early postseason elimination.

The dysfunctional negotiations that unfolded the next three days after that point ultimately led to Shanahan’s decision to move on.

“I just felt differently. And I felt that the long-term future of the Maple Leafs might have to change,” Shanahan said on Friday afternoon.

With Dubas now gone, Keefe will almost certainly be let go once a new GM is put into place, despite having a year remaining on his contract.

It’s also considered highly unlikely that capologist Brandon Pridham will get the GM job, given it’s vastly different than his experience and current responsibilities.

Even if Pridham stays in a complementary role, however, 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.

A new GM is likely to opt for a more traditional structure — and to bring in several of their own people.

In terms of who that GM might be, the frontrunner appears to be former Flames GM Brad Treliving, who has been in rumors behind the scenes going back to at least March. But I’m also hearing candidates could come in the form of current GMs or team presidents with other teams who have out clauses in their deals and who may be interested in the high-profile (and high-paying) role in Toronto.

Someone like Blues GM Doug Armstrong, who has plenty of experience and has won a Stanley Cup, could plausibly be an option, if he’s contractually able to leave St. Louis in the short window Shanahan has to make this hire.

However the GM search plays out, the Leafs are expected to hire someone who has NHL experience in the role. And it’s expected Shanahan will seek guidance from NHL commissioner Gary Bettman and the league office before making the hire, as many teams in this situation do.

As for the coaching staff, it’s believed that Joel Quenneville is intrigued by the idea of coming to Toronto. He has yet to meet with the league to be granted re-entry to the NHL after resigning as Panthers coach in October 2021 following the Blackhawks investigation into the sexual assault of former player Kyle Beach by video coach Brad Aldrich, however. As such, it feels unlikely the Leafs would be willing to make such a controversial hire at this time.

But it is safe to say that it will likely be a high-profile, experienced coach who replaces Keefe.

There’s a feeling high up in the organization that the team’s core players may benefit from a significant shakeup, including having less of a “players” coach and by trading a significant piece of the core.

While Shanahan will need a new GM in place to make moves like that, it’s apparent that whoever joins the Leafs in that role will likely be informed that more than cosmetic changes are required.

Given how complex the Leafs roster decisions are going to be this offseason, getting that GM hire right will be imperative. Without Dubas, the Leafs front office is low on experienced hands, and with so many currently in place contemplating their futures, the exodus could create even more uncertainty as the draft and free agency approach at the end of next month.

As for Dubas’ future, while he stated on Monday that he didn’t anticipate quickly relocating to a new role, the thinking around the league right now is that his views may change if he receives a significant offer in a role with full autonomy in the coming months. The situation in Ottawa, in particular, could be intriguing, with new, deep-pocketed ownership and a young roster on the rise.

A front office with the rival Senators that included Dubas as president and Spezza and Daniel Alfredsson in supporting roles would certainly make things interesting in the Atlantic Division.

Not that the Maple Leafs will need any help creating headlines at this point given the organizational upheaval that is going to continue to unfold this offseason.

(Photo: Rene Johnston / Toronto Star via Getty Images)

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