Brendan Shanahan’s 10-year run as Maple Leafs president brought stability and vision to a franchise in chaos—but the Stanley Cup chase remains unfinished.

Brendan Shanahan took over as president of the Toronto Maple Leafs in April 2014 with one clear goal: turn a struggling team into a consistent contender. A Hall of Famer with three Stanley Cups as a player, Shanahan arrived with instant credibility—and big expectations.

He didn’t promise a quick fix. Instead, he rolled out what fans came to call the “Shanaplan”—a long-term, structured rebuild focused on drafting, player development, and building from within. The goal was to move past the stopgap solutions and headline-grabbing trades that had defined the Leafs for years.

The early years were tough, but the payoff came quickly. By 2016, the team had drafted franchise centre Auston Matthews. The Leafs soon became a regular playoff team, with a core of young stars that finally gave fans hope.

Signing Johnny T.

One of Shanahan’s biggest moments came in 2018 when the Leafs signed John Tavares.

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A hometown star and one of the top free agents on the market, Tavares chose Toronto over teams like Boston and San Jose. The move sent a message: the Leafs were all-in.

Tavares was productive and professional, and his arrival signalled a new era. But the $11 million per year contract had ripple effects. It set the bar for what the Leafs’ other young stars—Matthews, Mitch Marner, and William Nylander—would ask for, leading to a top-heavy salary cap structure. That left little room for depth pieces, and critics argue the team became too reliant on its “Core Four.”

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Shanahan bet big, but the NHL’s cap system doesn’t always reward boldness. And when the playoffs came, that lack of depth often showed.

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Brendan Shanahan (left), John Tavares (middle), Kyle Dubas (right), pose after the press conference announcing John Tavares’ signing with Maple Leafs (Photo by: Brian Compton)

Some hits, some misses

Shanahan’s track record on trades and contracts was mixed.

  • Nazem Kadri Trade (2019): The Leafs traded Kadri to Colorado for defenceman Tyson Barrie and forward Alex Kerfoot. Barrie never found his footing in Toronto, and Kadri went on to win a Stanley Cup with the Avalanche in 2022. In hindsight, the deal didn’t age well.
  • Nikita Zaitsev & Patrick Marleau: Zaitsev’s early promise faded, and his long contract became a problem. The Leafs also had to give up a first-round pick to move Marleau’s salary. These were reminders of how quickly free-agent bets can backfire.
  • Goaltending: From Frederik Andersen to Jack Campbell and Petr Mrazek, stability in net remained elusive. Goalie inconsistency was a theme during Shanahan’s time, and that falls on team management.

Changing the culture off the ice

Where Shanahan made perhaps his biggest mark was in reshaping the Leafs’ organization from top to bottom.

He brought in Lou Lamoriello, then Kyle Dubas, and invested heavily in scouting, analytics, and player development. That front-office investment paid off with smarter drafting and a stronger prospect pipeline. Toronto also became a place top players wanted to go.

Hiring rookie GM Kyle Dubas and AHL coach Sheldon Keefe was a gamble, blending new-school thinking with NHL realities. There were growing pains—long negotiations with players like Marner, and questions about accountability—but the Leafs became a team that played fast, skilled hockey and stayed in the playoff mix.

The Leafs did well drafting stars like Matthews, Marner, and Nylander. But they struggled with asset management further down the lineup.

Prospects like Mason Marchment and Trevor Moore were let go too early, only to thrive elsewhere. Trades for short-term help—like Nick Foligno—cost Toronto young talent and draft capital without delivering playoff wins.

The Seattle Expansion Draft was another misstep. The Leafs chose to protect defenceman Justin Holl, leaving forward Jared McCann exposed. McCann broke out with Seattle, while Holl remained steady but unspectacular in Toronto.

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Brendan Shanahan smiles and jokes with reporters during a media scrum in 2024 (Photo by: NHL.com)

Wins beyond the scoreboard

If success was only measured in playoff rounds won, Shanahan’s tenure would look like a disappointment. The Leafs made the playoffs in seven of his 10 seasons but won just one series—against Tampa Bay in 2023. The collapses in 2018 (vs. Boston) and 2021 (blowing a 3–1 lead to Montreal) still sting.

But Shanahan didn’t just take over a hockey team—he took over a broken franchise. When he arrived, the Leafs hadn’t won a playoff series in over a decade and were a punchline in much of the hockey world.

His leadership changed that. The Leafs became a playoff team year in and year out. That wasn’t the norm before. Expectations shifted—fans now expected wins, not just appearances. The Leafs became one of the most talked-about teams in hockey, and that attention was no longer negative.

Behind the scenes, the team invested in modern training facilities, analytics, nutrition, mental health, and diversity programs. The Leafs became a first-class operation and a model that other teams looked to.

A legacy still evolving

Brendan Shanahan leaves Toronto with one major box unchecked: the Stanley Cup. For many, that’s the only thing that matters.

But his decade in charge brought stability, identity, and relevance to a team that had none. He made mistakes—big ones—but also helped raise the bar. Under Shanahan, the Leafs stopped being a sideshow and became a contender.

Whether that foundation leads to the Cup someday isn’t just up to him anymore. But his impact will be felt long after his exit. In the toughest market in hockey, Shanahan didn’t end the drought—but he made the Maple Leafs matter again.

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