After 11 years of tumult, progress and plateauing, the Brendan Shanahan era in Toronto came to a close Thursday as the Toronto Maple Leafs parted ways with the Hall of Famer who had served as the team’s president and alternate governor since 2014.
The exit came days after the Maple Leafs were ousted in the second round of the Stanley Cup Playoffs, bounced by the Florida Panthers for the second time in three seasons. But the path that led to the end of ‘The Shanaplan’ began much earlier, years ago, as the club descended into a pattern of run-it-back, hope-for-the-best seasons that yielded little in the way of improved results.
The Mimico, Ont., product leaves the Maple Leafs having authored a significant chapter in the club’s history. It was Shanahan, in the early years of his tenure, who tipped the team into a scorched-earth rebuild that wound up netting Auston Matthews and Mitch Marner, beginning a new era for the blue and white. Behind the scenes, it was Shanahan who repaired the bridge to the organization’s past, re-establishing a connection to the club’s storied alumni.
But it’s the last half-decade of his Toronto tenure that set Shanahan and the organization on the path to parting ways thanks to a string of repeated first-round playoff exits and the club’s stubborn adherence to going all in on a core of four highly paid forwards.
Shanahan was instrumental in taking Toronto from the playoff fringes back to the spotlight. But the inability of the group he built to get any further than that, to transition beyond mere playoff participant, brought the need for a new voice.
As his tenure in Toronto comes to an end, here’s a look at the best and worst of the Maple Leafs’ Shanahan era.
THE HITS
Bringing great expectations back to the Maple Leafs
While there are plenty of misses and missteps to cover, the bigger picture here can’t be ignored. Before Shanahan arrived in Toronto, the Maple Leafs had made the playoffs once in the previous decade. They finished sixth in the Atlantic Division and missed the post-season the year before he was hired — before that, they’d finished outside of their division’s top three in six of eight seasons, their only playoff appearance ending in the infamous ‘It was 4-1’ Game 7 heartbreak.
In Shanahan’s third season at the helm, Toronto returned to the playoffs. It’s qualified every year since, finishing top-three in its division for the past eight years and winning it twice. While the Maple Leafs haven’t yet managed to transition into the next echelon — from making the post-season to going on deep playoff runs, hanging banners — Shanahan’s guided the club to a place where those lofty expectations are both warranted and realistic. For a long time before his arrival, that wasn’t the case.
Drafting Matthew Knies, the second-round gem
The list of quality young talents the Maple Leafs have drafted over the past decade — outside of the core — isn’t lengthy. But Shanahan and his front office hit big on one at the 2021 NHL Draft when they selected Matthew Knies in the second round, 57th overall. The young winger has emerged as a key member of this club’s new core, and has already shown potential to be a great Leaf for years to come. Though he heard his name called at No. 57, to this point Knies has been a top-10 talent among his draft class, having amassed the sixth-most goals, ninth-most points and ninth-most NHL appearances of anyone selected in 2021.
Trading for defender Jake Muzzin, the Maple Leafs’ ‘conscience’
At the time, it seemed a crucial step forward for Toronto. In 2019, the Maple Leafs acquired Jake Muzzin from Los Angeles in exchange for a first-round pick, Sean Durzi and Carl Grundstrom. Muzzin was only a few years removed from lifting the Stanley Cup with the Kings and from helping Canada win the World Cup of Hockey on Toronto’s ice. He emerged as the Maple Leafs’ best defenceman, and more importantly, became the team’s “conscience,” as Sheldon Keefe described it — one of the few Leafs who was willing to hold the club accountable in the tough moments. If not for key injuries at key times, particularly in the post-season, the veteran might’ve made an even greater impact during his tenure.
Signing netminder Anthony Stolarz, the new No. 1
It’s perhaps a sign of the issues at play here that some of Toronto’s best moves came just this past off-season. After Shanahan brought in Brad Treliving to replace Kyle Dubas, the new GM hit some quality shots in his second season on the job, particularly in signing netminder Anthony Stolarz. The backup for Florida’s 2024 Cup run, Stolarz came in and seized his opportunity, posting a league-leading .926 save percentage and helping lead Toronto to a division title. Like Muzzin, injuries derailed his chance to have an even more significant impact, as he was sidelined after Game 1 of the Leafs’ second-round loss to Florida.
Rebuilding the Maple Leafs’ blue line, starting with Chris Tanev
As made clear by Toronto’s recent run, there might not have been a more impactful recent addition for the club than veteran defender Chris Tanev, who not only played incredibly well himself since joining the blue and white, but did so with an honest, hard-nosed approach that spread to the rest of the blue line corps, too. Beyond Tanev, Treliving and Co. managed over the past couple off-seasons to build what was clearly the best defence corps of the Shanahan era, acquiring Brandon Carlo and inking Simon Benoit and Oliver Ekman-Larsson, too. It was primarily because of this solid blue-line group that the Maple Leafs faithful went into these playoffs with renewed hope (before it was squandered once again).
Bringing in veteran talent to guide the young core
For a club whose success was so unavoidably tied to the development of three young, marquee talents, the organization did well in providing them quality veteran mentors. There were surely some misses — Joe Thornton, Nick Foligno, paying Patrick Marleau upwards of $6 million per year — but there were hits, too. Marleau might’ve been overpaid, but he turned in a 27-goal campaign. Jason Spezza joined the club after a quality half-decade in Dallas and gave Toronto some good years on a bargain deal. Max Pacioretty did the same this past season, and came up with some memorable post-season moments, including a series-clincher.
There’s no question the most impactful veteran addition up front, though, was John Tavares. Back in 2018, landing Tavares seemed like a coup for the Maple Leafs, a critical step forward. He was a two-time Hart Trophy nominee, a perennial All-Star. He gave Toronto a bona fide one-two punch down the middle, and seemed to represent a step forward for the young core. The hometown boy put up 47 goals and 88 points in his debut season in Toronto, went on to serve as a dutiful captain for the franchise and amassed nearly 500 total points in a Maple Leafs sweater. For his part, it’s tough to argue No. 91 didn’t deliver what was asked of him.
But bigger picture, signing Tavares in 2018 might’ve been the first crack in the Shanaplan. First, there was the question of whether the centre was truly what Toronto needed, given the potentially elite young talent it already had up front. There was an argument to be made that you could never have too many top-end forwards — but the lack of meaningful post-season success that’s followed seems to undercut that. More importantly, though, were the ripple effects of the decision to sign Tavares to a massive seven-year, $77-million deal, and the impact that would have on the hefty extensions to come. Which brings us to our next section.
THE MISSES
Mishandling crucial contract negotiations with The Core
Rewind back through the years, and you can trace much of what’s ailed this Maple Leafs era to the negotiations with the club’s young core forwards — William Nylander, Mitch Marner and Auston Matthews. In all three cases, fans were left with the impression that the front office capitulated to its players’ demands and allowed the young stars to max out financially, leading to a cap situation that’s hampered this club’s ability to build a winning team.
It’s primarily the negotiations with Nylander and Marner to which fans point, the sense that both players held the organization’s feet to the fire and ultimately saw the club cave. Both players held out for a spell when negotiating their first big-ticket extensions, and in the end, seemed to max out on their potential value. Matthews had more leverage as a first overall pick and an elite scorer from the jump, but there’s still the fact that his current deal allowed him both a cap hit that made him the league’s highest-paid player and a term of only four years, rather than the eight years that contemporaries like Nathan MacKinnon, Connor McDavid and Leon Draisaitl opted for.
What resulted from that front-office approach was a Maple Leafs squad with four forwards earning upwards of $10 million per year, a unique situation compared to the rest of the league, and one that has seemingly made building a complete team around even more difficult.
Trading away Nazem Kadri, and watching him become a winner
If you imagine precisely the type of player Toronto currently covets — that Sam Bennett-Brad Marchand type, the playoff dog who can mesh elite skill with on-the-line bite — you can already picture what it would look like in a Maple Leafs sweater, because Toronto had it in Nazem Kadri.
A seventh-overall pick for his boyhood club, Kadri’s 10-year tenure with the Maple Leafs descended into one of annual fanbase and front-office frustration over repeated playoff suspensions. So, in 2019, Toronto shipped him off to Colorado in exchange for a package highlighted by Tyson Barrie and Alex Kerfoot. Neither Barrie nor Kerfoot managed to make a meaningful impact in Toronto, while Kadri emerged as a key piece for the Avs, playing a pivotal role in their 2022 Stanley Cup run.
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Letting Zach Hyman walk and become a 50-goal scorer in Edmonton
Speaking of hometown talents who were pushed out the door, there’s the mishandling of Zach Hyman, too. If not for how it ended, Hyman would’ve been a clear win for the Shanahan era, having acquired him in exchange for Greg McKegg back in 2015 and developing him into a promising NHLer.
But when Hyman hit unrestricted free agency in 2021, the Maple Leafs decided against giving the two-time 20-goal-scorer too hefty a raise on his $2.5 million annual salary. Instead, the winger signed with Edmonton for $5.5 million per year. He scored a career-high 27 goals in his first season as an Oiler, a career-high 36 the next and a career-high 54 the year after that. Now, he’s currently in his second straight deep post-season run with Connor McDavid and Co.
Giving away depth scorers for seemingly no reason
Trading away Kadri for help on the blue line was one thing, but other instances of asset mismanagement seemed to take potential offensive help off the roster without reason. In 2020, there was the trade that sent Mason Marchment to Florida. Toronto had signed the undrafted Marchment to an AHL deal half a decade earlier, developed him with the Marlies and given him brief shots in the big leagues. But before truly seeing what he could do at the NHL level, the Maple Leafs traded him to Florida for Denis Malgin. Malgin played only eight games for Toronto during that stint, failing to record a point. Meanwhile, Marchment went to Florida and established himself as a quality depth piece before signing as a free agent in Dallas for $18 million.
The next year, there was the Jared McCann situation. Acquired from Pittsburgh in a bargain deal, McCann came to Toronto having just scored at a 25-goal, 60-point pace with the Penguins while seeing time on Sidney Crosby’s wing. Still, the Maple Leafs left him exposed in the 2021 Expansion Draft, where he was selected by the Seattle Kraken, instead choosing to protect Kerfoot and oft-maligned defender Justin Holl. McCann put up 27 goals in his first season with the Kraken, and 40 goals the next. Meanwhile, Toronto’s continued to search for depth at left wing.
Missing out on drafting quality young talent due to unforced errors
The Maple Leafs were far from the only club who took on a win-now approach and shipped out first-round picks to try to land deadline game-changers. The first-rounders given up to bring in the likes of Ryan O’Reilly and Nick Foligno might’ve been misguided in hindsight, but the motivation was clear. Less understandable were the first-rounders given away in pursuit of correcting the club’s own errors.
In 2022, Toronto traded a first-round pick to Chicago as a means of convincing the club to take netminder Petr Mrazek off their books. The Maple Leafs had signed Mrazek to a three-year, $11.4-million deal a year earlier (the same summer they let Hyman walk). A few years before that, in 2019, Toronto traded away a conditional first-round pick along with Marleau to Carolina in a deal made to provide the Maple Leafs with much-needed cap relief. It was perfect storm for the Dubas Era — Marleau had arguably been overpaid on his initial deal, the club had signed its core to hefty deals of their own, and now they were forced to lose a first-round pick to move out Marleau so they could re-sign the likes of Kasperi Kapanen and Andreas Johnsson, both of whom were traded the next year.
The Canes used the Maple Leafs’ first-round pick acquired in that Marleau deal to select Seth Jarvis, who’s since posted two 30-goal campaigns in Raleigh and helped Canada win gold at the 4 Nations Face-Off.
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Standing pat for too long, as evidence mounted that change was needed
Above all else, the primary misstep of the Maple Leafs’ Shanahan era was the club’s hesitance to make any significant changes, even as it became clear that some measure of change was needed. In the beginning, Shanahan did well in ushering in a new chapter for the franchise, bringing in a wave of young, elite talent who could lead Toronto back to the promised land. But when they hit a wall, stumbling through year after year of disappointing first-round exits, the Maple Leafs refused to adjust their approach, opting to keep running it back with the Core Four, hoping the same group might eventually find different results.
But it extended off the ice into the front office, too. After he took over as GM in 2018, replacing veteran Lou Lamoriello and beating out fellow assistant GM Mark Hunter for the job, Dubas oversaw four straight first-round exits — including particularly disappointing losses to Columbus and Montreal. He was ultimately let go after Toronto broke through that first-round wall only to get immediately bounced by Florida. The same went for Keefe, who was there for much of that run — rather than moving on from the coach the same summer the club parted ways with Dubas, when it seemed clear a new voice and a new direction was needed, Keefe was signed to an extension. Another first-round exit the next year led to his eventual exit, too. The result was a growing perception among the fanbase that the organization seemed to be resigned to complacency, allowing the same decision-makers to guide the same group, even as meaningful results eluded them.
Now, as Shanahan’s tenure comes to a close, that aversion to change has led to what might wind up the greatest failing of this front office’s era — losing Mitch Marner for nothing.
In the wake of a Leafs chapter defined by an unyielding belief in the Core Four, Toronto arrives at the 2025 off-season with Marner looking likely to walk away as an unrestricted free agent. That marks another perfect storm of this tumultuous era — a product of Shanahan’s front office falling short in building a winning team around him, of not getting him signed to extension before it reached this point, of refusing to trade him when a change seemed needed, and of turning over the front office when the timing for such a trade seemed right before the no-move protection in Marner’s contract kicked in.
As a result, the Maple Leafs seem poised to lose a premier asset for nothing — a 100-point, Selke Trophy nominee, a highlight-reel talent who sells jerseys and tickets and who surely could’ve fetched a sizeable package on the trade market. Or, No. 16 will return, sign a new deal and Toronto will run it back all over again.
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