Why the Maple Leafs had to finally end the Shanaplan

In the end, the legacy Brendan Shanahan leaves after 11 years as the Toronto Maple Leafs president is a complicated one.

When he was hired in the spring of 2014, theres no question the organization had fallen to laughingstock status, having missed the playoffs in eight of nine seasons and alienated fans and alumni alike.

Advertisement The decision to finally bottom out and rebuild, properly, through the draft beginning in earnest in 2015-16 when a last-place finish resulted in getting Auston Matthews first overall was a game-changer for a franchise that had long pursued misguided shortcuts.

There were skeptics when Shanahan was first hired by then-Maple Leaf Sports & Entertainment CEO and president Tim Leiweke.

Shanahan hadnt worked for a team.

His main credentials were a decorated Hall of Fame career and his tenure at the NHLs head office in New York, where he served as the league disciplinarian.

But those concerns melted away fairly quickly, as Shanahan won over the fan base and, most importantly, MLSEs board of directors.

He was charismatic and fearless in those early years, and the team finally started to win on the ice, making the playoffs in nine consecutive seasons.

The bar for professionalism in the organization had been on the floor, and he quickly raised it, using MLSEs considerable resources to build out an expensive staff full of big names and up-and-coming innovators.

In hindsight, however, the Shanaplans high point may have come early on, when a plucky young Leafs team with seven rookies on the roster unexpectedly made the playoffs in 2017 and pushed a star-studded Washington Capitals team to six games in a hard-fought first-round series.

For once, there was unbridled hope in Toronto, with a core group built around teenagers Matthews, Mitch Marner and William Nylander who seemed like they could bring sustained success.

It hasnt worked out that way, to the disappointment of the sports largest fan base.

Which is the biggest reason why it was not a surprise on Thursday when the Leafs announced Shanahans contract would not be renewed.

The No.

1 criticism he will face in the wake of the Leafs embarrassing Round 2 elimination last weekend is that he committed to an unsuccessful core group of players for too long.

Toronto had lost in the first round seven times in the previous eight years before this season, and there was never a true shakeup at the top of the roster.

Its best players were always sheltered, never facing consequences or accountability.

In fact, they all received raises, to the point the Leafs were the most top-heavy team in the NHL for the past six years.

This season, they had four players making $10.9 million or more in a league where only a dozen players make that much.

Shanahan has to own their failings in particular, as he was the Leafs biggest advocate for keeping that group together, year after year.

In fact, when he fired former GM Kyle Dubas in April 2023, he immediately reached out to his top players and assured them they were safe from being dealt.

This was before he had brought in Dubas replacement, Brad Treliving, who is remaining in place as GM.

Advertisement That decision to back all of his core players without a GM in place was emblematic of how Shanahan ran the team behind the scenes, however.

Multiple executives said he had final say on everything and had, over the years, nixed key decisions made by those under him.

That was part of what ultimately led to a falling out with Dubas that became public when the GM was offered a contract extension and then subsequently fired.

Over time, as the playoff disappointments piled up, the organization became a dysfunctional place, according to multiple members of the front office.

Different departments felt siloed off from one another, and Shanahan hired his own staffers whose roles were unclear to others.

Some of that confusion is likely due to the Leafs bloated organization chart, with various hires from previous regimes still in place among a staff of some 100-plus people.

Toronto currently has, for example, an NHL-high five assistant GMs on staff, as well as special adviser to the GM Shane Doan.

How the Leafs got here is at least in part related to Shanahans inexperience building an organization, which helped create a rotating door of squabbling coaches, GMs and other executives that followed their early exits over the years.

In 2015, for example, he hired head coach Mike Babcock on a record-breaking eight-year contract without having a GM in place.

He also placed inexperienced executives Kyle Dubas and Mark Hunter in charge of running the draft and hockey operations department, but they were at odds with one another.

Lou Lamoriello was hired later that summer to oversee the organization for the next three years, but he made some poor signings including Patrick Marleau and Nikita Zaitsev and his somewhat authoritarian style meant little mentorship of those under him was taking place.

Advertisement That ultimately led to more infighting and staff turnover.

In 2018, Dubas, then 32 years old, took over as GM under those less-than-ideal circumstances, which resulted in more glaring mistakes such as trading away the teams 13th overall pick in 2020 in order to dump the Marleau contract.

(The Carolina Hurricanes later landed star forward Seth Jarvis with that pick.) The Leafs front-office upheaval kept coming.

Hunter quit after Dubas was promoted.

Dubas and Babcock butted heads almost immediately, which led to the coachs firing early in an ugly 2019-20 season in which Toronto could have missed the playoffs if not for the pandemic shutting down the year.

Along the way, the Leafs continued to add more staff and executives, building out, among other things, the largest development and analytics staffs in the NHL.

Treliving, for his part, hired Doan and assistant GM Derek Clancey when he joined the organization two years ago while retaining Brandon Pridham, Hayley Wickenheiser, Darryl Metcalf and Ryan Hardy in senior leadership roles.

One key challenge facing MLSEs new CEO and president Keith Pelley who will take over Shanahans duties above Treliving, at least for now will be rebuilding this Frankenstein-like front office on the fly.

Pelley has said in the past he values culture and chemistry in organizations he has run, and both slipped over time under Shanahans watch.

More cuts are expected for the hockey operations department this offseason, adding to the 80 layoffs MLSE made earlier this year in other parts of the company.

The decision-making process will be streamlined, too, from what it became under Shanahan.

The Leafs face a daunting task in attempting to improve their roster this summer and have greater playoff success next spring while also likely losing star winger Mitch Marner for nothing to free agency.

Advertisement Treliving will have plenty of money to spend but also plenty of holes to fill, especially up front.

With the NHLs salary cap climbing dramatically, the Leafs wont be alone in their ability to add big contracts, which will drive up prices league-wide.

And other than Marner, the NHLs UFA class is underwhelming this year.

The degree to which Treliving succeeds in this new structure over the coming weeks will likely have a bearing on how the Leafs front office is shaped and whether or not Pelley decides he needs to add another layer above his GM.

Shanahan deserves credit for taking the organization out of the dark ages, bringing in star players, building a consistent playoff team and honouring the teams alumni and 100-plus year history.

But he has also left the Leafs with significant challenges to surmount, on the roster and behind the scenes.

Whats clear is that it was definitely time to move on from the Shanaplan.

Eleven years in one place is a long time for any executive in the NHL, longer than all but three GMs have been in place around the league.

Eleven years without going deep in the postseason, meanwhile, is an eternity.

(Top photo: Steve Russell / Toronto Star via Getty Images).

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