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Much has been said about the Maple Leafs’ decline this season, and rightly so. The team has shifted from a serious Stanley Cup contender just three years ago to a potential lottery pick this year.

Along the way, several targets have drawn criticism from Leafs fans and the media alike. From former head coach Mike Babcock to ex-GM Kyle Dubas and current captain Auston Matthews, no one has escaped the fans’ wrath or the media glare.

Still, amid all the turmoil, it’s unclear what specific factors brought about the end of an era that started with great promise and finished with a whimper this season.

Noticeably missing from the paragraph above is the name Brendan Shanahan, the man who sparked this entire era from the moment he was hired in April 2014. Shanahan was appointed president and alternate governor at the time and oversaw all Maple Leafs operations.

Some may forget, but back then, questions arose about whether Shanahan had the experience for such a role. Fair or unfair, those questions were valid since he was only five years removed from his last NHL game and lacked prior executive experience with an NHL team.

Shanahan did have executive experience, working at the NHL’s head office after his playing career. He was hired in December 2009 as the league’s vice president of hockey and business development and served in that role for just over a year before succeeding Colin Campbell as the senior vice president in June 2011.

Much of Shanahan’s role involved issuing suspensions for illegal hits and plays, and Shanahan modernized this system by introducing videos in which he narrated the plays in question. While this was relevant experience for an executive role in an NHL club, it is fair to question whether Shanahan had the appropriate experience to make management, coaching, and player personnel decisions and oversee the entire operation.

Ultimately, Shanahan was responsible for many of the key figures involved in this era of Maple Leafs hockey. Shanahan brought in figures like Babcock, Dubas, Lou Lamoriello, and eventually Brad Treliving. These men played major roles in shaping the team, from the coaching staff to the backup goaltender.

It’s impossible to know who made the final decisions on every move, but since Babcock, Dubas, and Lamoriello all exited at different times, it’s fair to say Shanahan held the overall authority and was accountable for nearly everything that occurred under his leadership.

So, what actions did Shanahan take when Lamoriello was in charge? There were certainly some good and bad decisions, but overall, they didn’t lead to the downfall this piece suggests.

Lamoriello attached the Maple Leafs to some problematic contracts during his time as general manager. Nikita Zaitsev received a seven-year, $31.5MM extension that proved disastrous and led to his trade, along with forward Connor Brown.

Patrick Marleau was signed as a free agent to a three-year deal worth $6.25MM per year. Toronto had to trade Marleau’s contract along with a first-round pick in 2019 because of salary-cap pressure.

There was also a four-year deal for veteran forward Matt Martin at $2.5MM per season, another far-from-ideal contract that took up valuable cap space. Although these contracts weren’t great and cost assets to unload, none of this was catastrophic, and Lou was out of Toronto before any serious damage was done.

Moving on from Lamoriello to Dubas, much of his work has been criticized as the downfall of the Maple Leafs. Dubas became a popular target for Maple Leafs fans, blamed for the decline of this era of hockey in Toronto.

It’s hard to judge if these criticisms are fair, considering we don’t know how much power Dubas actually held or how much veto power Shanahan exercised. It’s also fair to look at Dubas’ record in Pittsburgh and wonder if he learned from his mistakes in Toronto or if he is now benefiting from full autonomy in his new role with the Penguins.

But was the Dubas era in Toronto really that bad?

Dubas was responsible for the large contracts awarded to the Big Three after their entry-level deals expired. He signed William Nylander to a six-year deal, Auston Matthews to a five-year contract, and Mitch Marner to a six-year agreement. He also signed UFA John Tavares to a seven-year, $77MM deal, which many felt was unnecessary because it led to the departure of fellow center Nazem Kadri, who was traded to the Colorado Avalanche in a move that didn’t work out for Tyson Barrie.

The Kadri trade is probably the biggest blemish on Dubas’s resume, although some fans might argue that other moves by Dubas, such as the Morgan Rielly extension, the Petr Mrazek signing, and the subsequent trade that saw Toronto give up a first-round pick to rid itself of his contract, are also questionable.

Signing the big four essentially meant the Maple Leafs had to spend nearly $40MM of their cap space on four players, and there is a fair argument that this forced Dubas to tighten the budget elsewhere on the roster. While that’s true, Dubas managed to find affordable depth over the years, with Michael Bunting being a good example.

There was also significant criticism of Dubas’ handling of several trade deadlines, during which he traded away many assets for short-term rentals. Despite these additions late in the season (such as Ryan O’Reilly, for example), Toronto was never able to get past the second round, and in most cases, they couldn’t win a single series.

While this isn’t entirely Dubas’ fault, he bears most of the criticism, since it was technically his decision to go all-in at these deadlines. He also left the Maple Leafs with many assets missing when he was dismissed.

Without delving too much into the drama surrounding Dubas’s departure, it seemed to be something that wasn’t part of Shanahan’s plan and ultimately led to the hiring of Treliving as general manager. Despite some of the flaws on Dubas’ résumé, it was difficult to argue at the time that moving to Treliving was an upgrade for Toronto. Treliving had just left his role as GM in Calgary, leaving the Flames with an aging, costly core that wasn’t a playoff team and needed a rebuild.

Treliving arrived in Toronto and enjoyed a fairly good first summer with the Maple Leafs as he signed Max Domi and Tyler Bertuzzi to one-year contracts. These moves provided the Maple Leafs with some flexibility, but that suddenly diminished when Matthews signed a four-year extension in August 2023, making him the NHL’s highest-paid player at that time with a $13.25MM AAV.

A few months later, Treliving managed to sign Nylander to an eight-year deal worth $92MM. This was the first time the Maple Leafs had secured a member of the original Big Three with a maximum-length contract. Neither of the contracts for Matthews nor Nylander was particularly egregious; however, they fully committed Toronto to this core, a group that had not reached the third round of the playoffs.

Treliving didn’t do too badly in the UFA market, although signing Domi to a four-year extension after his first season in Toronto was a risky move that hasn’t worked out. Another tough contract to evaluate now is the six-year deal with defenseman Chris Tanev, which still has four years remaining after this season.

Those two deals essentially committed Toronto to $8.25MM in salary for two veteran players whose best years are behind them. This pattern reflects a tendency Treliving has often shown throughout his career as a GM.

Treliving’s first two seasons with Toronto were mostly decent, as the Maple Leafs made the playoffs and even won the Atlantic Division in 2025. The pivotal moment in his tenure occurred in the summer of 2025 when it became evident that Marner was planning to leave Toronto.

The star forward headed to Vegas, and although Treliving managed to acquire Nicolas Roy in a trade for Marner, what followed revealed a GM who was unprepared for the situation. Treliving’s moves after Marner’s departure didn’t make a significant difference and did little to replace the scoring loss.

Dakota Joshua, Matias Maccelli, and Roy were brought in, and it was assumed these three could fill Marner’s scoring gap. He couldn’t have been more wrong. Not only did they fail to replace Marner’s scoring, but they also left the Maple Leafs with a roster that was ineffective defensively.

Now, Treliving is left in Toronto as the de facto last man standing from a management regime that will likely be criticized for decades for squandering a golden opportunity to bring a Stanley Cup to Toronto. Folks will point fingers and blame the hierarchy from Shanahan to the backup goaltender, but the truth is this: The Maple Leafs’ downfall was not immediate; it was built on bad hires, bad trades, bad signings, and bad bets.

While it’s hard to narrow ten years down to one defining moment, there is a key two-month period that occurred in 2023.

The two moments that stand out as the beginning of Toronto’s decline are the firing of Dubas in May 2023 and Mitch Marner’s no-move clause kicking in on July 1, 2023. It’s long been speculated that Dubas wanted to reshape the Maple Leafs roster if he remained in the GM role, but he was fired before he could do so, and Toronto let Marner’s no-move condition trigger in his contract.

Dubas’ firing led to the hiring of Treliving and to the recent three seasons of moves in Toronto (including Marner’s departure). Now, most people will compare Treliving’s record to Dubas’s and claim Treliving has been more successful as a GM.

However, Dubas inherited a complete mess in Pittsburgh, as the Penguins were old, stagnant, in cap trouble, and lacked prospects. Treliving, on the other hand, inherited a top team in the Eastern Conference and kept it competitive for two seasons. It’s an apples-to-oranges comparison between Dubas and Treliving; however, one crucial fact remains: Dubas put the Penguins on the upswing, while Treliving has overseen the Maple Leafs’ decline.

Then there is Marner, who was never traded until the summer of 2025, and fetched only Roy in return for the Maple Leafs. Losing a top NHL player and failing to recoup the asset were major cases of disastrous asset management.

Sure, the Maple Leafs got two extra years of Marner, but not trading him in 2023 would have allowed them to acquire a haul of players back then and give Matthews, Tavares, and Nylander more depth.

That eight-week period in the spring of 2023 was a turning point, and for Maple Leafs fans, it’s hard not to look back and wonder what would have happened if Dubas had stayed in Toronto and Shanahan had been the one to depart.

We’ll never know, and for Maple Leafs fans, it doesn’t do any good to speculate; the era is over, and what comes next is unknown.

Photo by Nick Turchiaro-USA TODAY Sports