Brendan Shanahan had plenty of success with the Leafs, but not enough to overcome one significant failure

Toronto Star

23-05-2025

When Brendan Shanahan came to Toronto, with the Maple Leafs' Stanley Cup drought approaching 50 years, he seemed like the right man for the impossible job. But the drought is almost 60 now, the longest any fan base has had to wait.
And Thursday, after 11 years of incredibly unfulfilling success as team president, Maple Leaf Sports & Entertainment decided not to offer Shanahan a contract extension. As unique as he was, Shanahan's time with the Leafs has concluded the way every Leafs executive's time since 1967 has concluded: without a Cup, without lasting success, and trailed by the lingering echo of disappointment. The Shanaplan era is over.
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'Toronto is where I was born and raised, where my family still lives, and being a part of this historic franchise will always be one of the greatest honours of my life,' Shanahan said in a statement.
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To be clear: there was success. The Leafs have reached the playoffs nine consecutive years, something they hadn't done since their last Cup in 1967, in the final year of a six-team league. When Shanahan was hired in 2014, the Leafs had reached the playoffs once since 2004.
He professionalized a shambolic organization, built a modern and multi-faceted front office, and set course, finally, for a patient rebuild. Even among Canadian franchises the Leafs were largely notable for going nowhere, but as fast as they could.
Shanahan had the resumé, to a degree. He was a skilled, tough player; his hockey journey touched so many aspects of the game's history that he should write a book. (He insists he won't.) He was considered one of the brightest minds in hockey, led the revival of the game back toward offence in 2004, cracked down on head shots as the league's chief disciplinarian, and was hired by then-MLSE CEO Tim Leiweke in 2014, alongside Raptors counterpart Masai Ujiri.
And Shanahan was a hometown guy who, when he won the Cup the first time as a player, took it to Apache Burgers on Dundas Street West. The Etobicoke native was the youngest of four Irish-Canadian brothers, and would say if there was only one potato on the table he'd get it. He won three Cups and Olympic gold and made the Hockey Hall of Fame, but fixing the Leafs meant a lot to him.
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'Being born in Toronto does not necessarily make you a good executive with the Toronto Maple Leafs,' he told me in 2014, after being given the keys as team president. 'But this … was a very personal decision. This, to me, would mean more than anything I was able to accomplish as a player, because I am so emotionally invested in this place.'
Shanahan rebuilt ties with alumni, Dave Keon above all. Game operations went from tin-eared to professional. He created Legends Row outside, retired jerseys inside, and turned the Leafs into a respectable organization off the ice. People forget how bad it was before Shanahan arrived.
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But he had never run a team, and somehow had limited networks in the game. He started with his management mentor Lou Lamoriello as GM, and his old coach Mike Babcock as head coach. Shanahan also cast around hockey for the smartest people he could find, and came up with Mark Hunter from the London Knights, and Kyle Dubas from the Soo Greyhounds.
The Leafs hit on draft picks in successive drafts — William Nylander, Mitch Marner, Auston Matthews — but never delivered in the playoffs and the wreckage piled up. The big stars extracted big contracts from the club — there was never a sense of taking less to help the team, even if John Tavares could have made more in San Jose. Shanahan fired Lamoriello and replaced him with Dubas; the organization fired Babcock, and replaced him with Dubas's coach in Sault Ste. Marie, Sheldon Keefe.
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Analysis
The Shanaplan for the Leafs looked promising. Then along came the playoffs
No one doubts the individual skill of the Leafs' Core Four of Matthews, Marner, Nylander and
And Shanahan's strengths turned into weaknesses. He knew Toronto's failure often came as a result of impatience and pressure, so he vowed to block out the noise and be patient. He believed in measuring players by how they played in big games, but also believed failure would drive great players to become tougher in those big games. In Toronto, the latter overrode the former.
So the Core Four of Matthews, Marner, Nylander and Tavares stayed. When Dubas finally decided he was going to change the core, he and Shanahan split. And every year — even the two years in which the Leafs actually won first-round playoff series — an embarrassing or dispiriting ending awaited.
Shanahan was a big-game player who couldn't see his best guys weren't big-game players; he was a heart-and-soul obsessive who couldn't agree when Dubas decided Toronto's best players didn't hate losing enough to change.
The Leafs have never been more methodical, more organizationally ambitious, and somehow, more disappointing, if only because unlike in the Harold Ballard years or the brief flashes of Doug Gilmour or Mats Sundin, this group had a long runway, real talent, and a chance to finally, finally, do something for the tortured fans in this cursed town.
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It often seemed like Mike Babcock was trying to sabotage his development. And the team lowballed
They failed, and Brendan Shanahan failed with them. And the Maple Leafs, once again, will have to try something new.