A timeline of Brendan Shanahan’s tenure with the Leafs

Brendan Shanahan’s tenure with the Toronto Maple Leafs is coming to an end, after both parties decided to part ways following an 11-year relationship. It started out with tremendous optimism, but following a 6-1 collapse against the Florida Panthers in Game 7, it became readily apparent that the MLSE Board of Directors wanted a major change.

Here are some key events that marked Shanahan’s tenure with the Maple Leafs:

April 11, 2014: Shanahan is officially announced as the president and alternate governor of the Maple Leafs. At the time, Shanahan’s hiring was viewed with real optimism, with an inclination that he would be the right fit to oversee a promising decade of Leafs hockey, stemming from his previous experience with the NHL as a senior vice-president.

July 2014: Shanahan hires Kyle Dubas as an assistant general manager. Dubas built an impressive profile as the general manager of the Soo Greyhounds and he made a strong impression on Shanahan during their initial meeting. It was a relationship that quickly developed and Dubas was clearly a candidate that Shanahan viewed strongly from the outset.

“I did think at the time he had the promise to be a general manager,” Shanahan said to The Canadian Press, upon promoting Dubas to GM in 2018. “Certainly as I got to see him evolve and grow here with the Maple Leafs, he was absolutely an option that I didn’t want to let go of.”

January 6, 2015: Shanahan fires head coach Randy Carlyle, as the Maple Leafs stumbled through the holiday stretch and he had seen enough, following a 5-1 loss to the Winnipeg Jets. Peter Horachek was promoted in an interim capacity the following day.

April 12, 2015: Horachek’s reign didn’t last long, as Shanahan dismisses him, along with GM Dave Nonis, continuing his overhaul of the executive branch, as the Maple Leafs continued in their rebuild. Shanahan wasn’t content with prolonged losing and he went after his top target aggressively.

May 20, 2015: Mike Babcock is announced as the 39th head coach in Maple Leafs history. Babcock joined the Maple Leafs on an eight-year contract worth $50 million, making him the highest-paid coach in the NHL by a massive margin. Toronto effectively won a bidding war for Babcock’s services, with the Buffalo Sabres and San Jose Sharks also expressing interest in hiring the Olympic gold medalist.

“I’m proud of Shanny, I’m proud that he dreamt big,” Maple Leaf Sports & Entertainment president and CEO Tim Leiweke said. “He got the big whale.”

June 26, 2015: Mitch Marner is selected fourth overall by the Maple Leafs in the 2015 NHL Draft.

July 1, 2015: In an effort to accelerate the team’s rebuild, the Maple Leafs trade Phil Kessel, Tyler Biggs, Tim Erixon, and a conditional second-round pick to the Pittsburgh Penguins for Kasperi Kapanen, Scott Harrington, Nick Spaling, a conditional first-round pick (later traded to the Anaheim Ducks) and a conditional third-round pick. Kapanen played a depth role for the Maple Leafs, Harrington was later traded to the Columbus Blue Jackets for Kerby Rychel, and the return was underwhelming in retrospect. As for Kessel, who was often unfairly maligned by his critics during his Leafs tenure: he won consecutive Stanley Cups with the Penguins, then added a third ring in 2023 with the Vegas Golden Knights.

July 24, 2015: Lou Lamioriello is hired as the next general manager of the Toronto Maple Leafs. Lamoriello and Shanahan have a deep affinity for each other, as the latter was the first player that the former New Jersey Devils executive drafted. It was an ill-fated partnership this time around and eventually, Shanahan reduced his mentor’s role to a special advisory capacity in April 2018.

April 30, 2016: The ping-pong balls bounced in the Maple Leafs’ favour, winning the first overall selection in the draft lottery, boasting 20 percent odds entering the night. Toronto used the pick to select Auston Matthews on June 24, 2016, the moment that for all intents and purposes ended the Maple Leafs’ rebuild.

July 1, 2018: John Tavares signs a seven-year contract worth $11 million annually, then posts on Twitter how it’s always been a childhood dream to join the Maple Leafs. This officially marks the start of the Core Four era, it’s the first time the Maple Leafs landed a top-of-the-market free agent in decades, and there’s a premonition that it’s just a matter of time before this group lifts the Stanley Cup.

November 20, 2019: Babcock was tasked with leading to the Leafs to a Stanley Cup, but the decorated head coach’s tactics and treatment of players was out of place in the modern era. As the team slumped on a six-game losing streak, with allegations rising to the surface about Babcock’s mistreatment of Marner, the Leafs fire Babcock following a 4-2 loss to the Vegas Golden Knights. Sheldon Keefe is appointed as Babcock’s successor.

May 15, 2013: Kyle Dubas was extremely candid during his end-of-year media availability, where he told reporters that he needed to consult with his family upon making a decision whether to return to the Maple Leafs.

“I think it requires me to have a full family discussion,” Dubas said. “My family is a hugely important part of what I do, so for me to commit to anything without having a fuller understanding of what this year took on them is probably unfair for me to answer where I’m at. I wish I could give you more. It was a very hard year on them.”

Toronto finally advanced past the first round of the playoffs, but were eliminated in five games by the Florida Panthers in the second round. Dubas sat alone at the podium, answered questions honestly and emotionally, but it was his final appearance as a part of the Maple Leafs organization.

May 19, 2023: During a chaotic week behind the scenes, Shanahan reveals that the Maple Leafs fired Dubas and explained his rationale. Shanahan also offered that he didn’t expect Dubas to be so forthcoming about the personal toll that the 2022-23 season took on him.

“I didn’t expect he was going to go out and put that to the public, but nevertheless it made it all the more real and all the more serious,” Shanahan said. “It certainly presented lots of questions. I have no issues with Kyle’s honesty, Kyle’s emotions. Kyle is an honest person.”

Shanahan stated that he wanted his next general manager to have previous experience, limiting his search pool, and Brad Treliving emerged as the obvious front-runner.

May 31, 2023: Treliving is hired as the next general manager of the Toronto Maple Leafs. It’s clear that the Maple Leafs are now fully built in Shanahan’s mold.

May 9, 2024: Shanahan and Treliving elect to fire head coach Sheldon Keefe. Keefe promptly joined the New Jersey Devils as their next head coach on May 23.

May 10, 2024: Shanahan had been reclusive throughout his tenure with the Maple Leafs, but took the blame for the team’s first-round elimination in 2024. The clock started ticking on his tenure, and entering the 2024-25 season on an expiring contract, Shanahan takes the more accountability than ever before during his decade-long tenure, before receding back out of public view for the vast majority of the 2024-25 campaign.

“The ultimate responsibility is on me,” Shanahan said during his 2024 end-of-year media availability. “The accountability is on me. Our playoff results haven’t been good enough. That’s on me. The results we’ve had in the playoffs, our players know, we know, they’re unacceptable. They’re unacceptable to our fans. They’re unacceptable to all those that support the Toronto Maple Leafs.”

May 17, 2024: Craig Berube is named as the next Maple Leafs head coach. Berube is formally introduced on May 21.

“To hold players accountable and for players to understand the accountability, you have to form a partnership throughout, I think it starts in the summertime,” Berube said. “Get to know these players, then get to understand what I’m all about and how I’m going to coach each individual and the team.”

May 22, 2025: MLSE CEO Keith Pelley announces that the organization will not be renewing Shanahan’s contract for the 2025-26 season.