The Toronto Maple Leafs were eliminated from the Stanley Cup playoffs in a sudden-death, winner-take-all deciding game of a playoff series yet again.
Claiming “if the Leafs don’t win this series, there will be major changes” has become such a tired phrase in the media circles surrounding this team, uttered so often but never true. Yet this time it is likely true. After this defeat, a 6-1 loss to the Florida Panthers in Game 7 of the second round, team President Brendan Shanahan, the architect of the past decade of Leafs hockey, will likely not see his contract renewed. Mitch Marner, one of the team’s most recognizable star players, appears more likely than not to depart in free agency.
With it would come the end of the “Core Four” era, launched the day John Tavares signed on July 1, 2018, seven years ago. To some, it stretches back further, to the fall of 2016 when Auston Matthews and Marner made their NHL debuts. This core group of players — those two, plus William Nylander and Morgan Rielly — has been together for nine seasons. With John Tavares included, it has been seven seasons. A period of infinite promise that seemed destined to finally bring the Stanley Cup back to Toronto will not do so. It may happen with some of these players in the future, but not with this iteration of the team. The Core Four and the Shanaplan, as we knew it, failed.
How did it all go wrong? What could have been different with more effective management? Today, we will walk through it all with one last history and farewell of the Core Four-era, Shanahan-led Toronto Maple Leafs:
The Early Years of the Shanaplan
The strangest thing about the first few years of the Brendan Shanahan era (Shanahan was hired in April 2014) is that the Maple Leafs were in a rebuild that ostensibly worked like a charm, yet mistakes were made that haunted the team down the road.
What worked about the 2014-16 rebuild is that the Maple Leafs drafted three times in the first round and, on paper, hit a home run all three times. William Nylander, Mitch Marner, and Auston Matthews are all All-Star forwards who are among the most offensively talented to ever wear the blue & white. These are three phenomenal, all-world players. They are the kind of players every team undergoing a rebuild dreams of acquiring with their top picks.
Those three young forwards were productive almost immediately after arriving in the NHL. The Leafs plugged them into a team that wasn’t as bad as it seemed, jumping from worst in the NHL in 2015-16 to a playoff spot in 2016-17. How well the Maple Leafs did in the first round of those rebuild drafts powered their rapid turnaround and quick ascension out of a rebuild, an outcome that escaped contemporary and future rebuilding teams like Buffalo, Ottawa, and Detroit.
Yet we can also look back on the rebuild years and find warning signs or at least areas of debate. For one, the Maple Leafs didn’t bottom out as hard as they could’ve. While they sold off some pieces, they held on to players like James van Riemsdyk and Nazem Kadri, who could’ve returned a decent package of draft picks. Compared to teams like Chicago and San Jose, who are currently in rebuilds and stripped it down to the absolute studs, the Leafs didn’t tank that aggressively. Indeed, the year they finished last in the NHL (2015-16), they did so with 69 points. In 2022-23, a 69-point season would’ve been sixth-worst in the NHL. It wasn’t the world’s most aggressive or elongated tank, but they took advantage of a year when few teams in the NHL were slashing the tires.
The decision not to burn it all down meant there were fewer bullets in the chamber in terms of draft capital. Still, the Leafs possessed sizable draft capital overall, picking 26 times between 2014 and 2016, and one of those drafts (2015) is considered one of the deepest and most talented in NHL history. The Leafs proved unable to fully take advantage of so many picks, trading down in the draft to stockpile picks but unable to turn those selections into much of note.
In the 2015 Draft, the Leafs traded out of the first round (they held 24th overall from Nashville in the Cody Franson trade) in exchange for later picks. The three picks they received were spent on Travis Dermott, Jeremy Bracco, and Martins Dzierkals. The pick they could’ve kept was used by Philadelphia to take Travis Konecny, a two-time All-Star.
For as well as the Maple Leafs did with their first-rounders from 2014-16, they got little out of their other selections. Of the 23 picks the Leafs took outside of the first round, they produced few players of consequence, only one of whom is still on the Leafs. Only five players out of the 23 played 50 NHL games: Pierre Engvall, Dakota Joshua (who never signed with the Leafs), Travis Dermott, Joseph Woll, and Carl Grundstrom. If you’re counting at home, that is four bottom-of-the-lineup sort of players and Woll, a goalie with frequent injury issues who took seven years to become an NHL mainstay. Meanwhile, players such as Roope Hintz, Sebastian Aho, Brandon Carlo, Rasmus Andersson, Vince Dunn, Anthony Cirelli, Nick Roy, Conor Garland, Niko Mikkola, Troy Terry, Vladislav Gavrikov, and Matt Roy were taken outside the first round in just the 2015 draft alone.
The end result of these draft shortcomings was leaving the Leafs light on other young, talented players to support the core, or lighter than they could have been. There were other useful players around at that point, like Kasperi Kapanen (acquired in the Kessel trade), Andreas Johnsson, Connor Brown, and Zach Hyman. But there could have been more in-house support with stronger drafts, particularly in the net and on the blue line. To the latter point, the Leafs spent just eight of the 26 picks they made between 2014 and 2016 on defensemen. Unsurprisingly, they made little progress on a home-grown blue line.
The 2016 trade for Frederik Andersen, shipping out a first and second rounder for an NHL goalie while the team was still rebuilding, showed a habit of accelerating the rebuild. That continued in 2016-17 when the Leafs traded their own second-round pick for Brian Boyle, a veteran who played a total of 27 games (regular season + playoffs) for the franchise. For a team not yet a contender with several rookies on the roster, it was a bold decision to burn picks on rentals. The 2017 draft saw them select once in the first round at 17th overall, selecting D Timothy Liljegren, a frustrating player who took a long time to reach the NHL and was never truly trusted as a playoff defenseman in Toronto. They also made six other selections in that draft, none of whom reached the NHL.
The 2018 draft was the final one to happen when the core was young and still on entry-level deals, before the routine of trading first-rounders for win-now players began. They picked once, at 29th overall after a trade back, and eight more times the rest of the draft. There was better success with this draft, but first-round pick D Rasmus Sandin ultimately never lasted with the franchise, dealt away to Washington five years later after he, like Liljegren, was not trusted to play playoff hockey. The second most promising player in that draft, D Sean Durzi, was traded away within a year for Jake Muzzin, and only one other player from the draft played more than 10 games in the NHL, forward Pontus Holmberg.
In total, over five crucial drafts from 2014-18, the Leafs selected three future superstars in the first round and unearthed relatively little else to support them. A few players, like Dermott, Sandin, and Liljegren, were around for several years but ultimately failed to materialize into mainstay performers. Many others never made a splash at all. When we consider how many times the Maple Leafs selected and how talented some of those draft classes were, it is an underwhelming yield. Had one of Marner or Nylander turned out to be a bust, the whole rebuild project may have failed with such little organic support in the pipeline. But they hit such breathtaking home runs in the first round, and had enough existing talent at the NHL level, that the Leafs returned to the postseason anyway.
The Birth of the Core Four
The 2014-18 rebuild drafts are a crucial part of the story that laid a shakier foundation underneath the top-end talent, a part of the story told before it all changed in July 2018, when John Tavares signed with the Leafs. The homecoming story of a superstar player who was a finalist for the Hart Trophy sent Leafs Nation into a frenzy. The concept of the “Core Four” — Matthews, Marner, Nylander, and Tavares — was born.
There was only one problem: Matthews, Marner, and Nylander were all unsigned long-term. Matthews and Marner were eligible for extensions with one year remaining on their entry-level contracts, while Nylander entered restricted free agency without a contract. Arguably, signing Tavares before taking care of the other contracts established an “internal cap” structure and a culture of paying top dollar for talent. Moreover, the young core could compare themselves to Tavares and drive up their own price.
However, the Leafs should have been more grounded and acknowledged that Tavares was a UFA and their core players were RFAs, making any comparison misguided. But they didn’t seem prepared to dig in and wield their leverage to win the negotiations, especially not after what happened with Nylander’s negotiation. Nylander held out and missed the beginning of the 2018-19 season, a holdout that led to Nylander posting career-worst numbers after signing, unable to find his groove after missing training camp. Perhaps out of a desire to avoid two future holdouts, Toronto’s management bowed down by handing Auston Matthews more than Tavares annually, five years at $11.64 million — less than Connor McDavid, but not the same length of commitment as McDavid gave the Oilers.
But the contract saga that really epitomized it all was the battle between Mitch Marner and the Leafs. Marner’s camp held up the Tavares comparable, as well as Matthews’ deal, and drew a hard line in the sand. They demanded similar money, even though the true comparisons for Marner’s production and the stage of his career were nowhere close to what he was demanding. After weeks of working the media, leaking to Darren Dreger and other insiders that an offer sheet with Columbus was coming or even that Marner could defect to play in Switzerland, the Marner camp got everything they wanted, as GM Kyle Dubas caved under pressure.
Marner signed a six-year contract with an average value of $10.9 million, a deal that is still outrageous to this day. Compared to fellow RFAs who signed around the same time, such as Mikko Rantanen and Brayden Point, Marner’s deal was ridiculous, which was clear at the time. He was paid more than the comparable players for fewer years and with more trade protection, something that would loom larger later on. There was no precedent for the deal Marner got, the work of a green GM for whom the lights were too bright.
By the beginning of the 2019-20 season, the culture was set, with immense power for the players and very little control for management. Players could name their price, management was going to cave, and the Leafs wound up with one of the most expensive collections of four players in the league. Between Tavares, Marner, Matthews, and Nylander, the Leafs were set to pay these four players $40.5 million, roughly half of a then-$81.5 million salary cap. Resources for depth additions were strained, making it extra useful to have young players and prospects ready to arrive in the NHL and provide quality production on the cheap. Unfortunately, as mentioned previously, inadequacies with drafting and developing meant that much internal help wasn’t going to arrive.
Building Around the Core Four
Once the Core Four era was locked in, difficult decisions had to be made about how to maximize the available remaining space. This problem was exacerbated when the COVID-19 pandemic froze the salary cap artificially for years on end, a problem no one could’ve seen coming and disproportionately affected the Maple Leafs, who shelled out for large contracts just months beforehand, banking on the cap perpetually rising. Instead, over the life of the six-year contract handed out to Marner, the cap rose just $6.5 million, from $81.5 million to $88 million.
Leafs brass had to be smart in their quest to build around the Core Four but proved only mediocre at it. Early errors were made by GM Lou Lamoriello, who signed Nikita Zaitsev to an ugly seven-year, $31.5 million contract. Also regrettable was the three-year deal handed to Patrick Marleau with an average value of $6.25 million per season. Marleau, besides ostensibly representing the worst possible veteran to mentor young players, given how his San Jose Sharks were defined by choking and underperforming (and Marleau losing the captaincy), also was not very good at hockey anymore. He turned 38 before the contract even began and had scored only 46 and 48 points the prior two years.
Marleau’s high cap hit became a major problem after signing the Core Four, since the soon-to-be-40-year-old version of Marleau was a highly replaceable player making a sizable salary. Rather than buying Marleau out or biting the bullet of stomaching one last year before it was over, Dubas (who had succeeded Lamoriello) traded a first-round pick to Carolina so the Hurricanes could swallow just a single year of the contract. It was one of the highest prices paid over the next five years to unload a single year of a contract, but the mismanagement of the contract negotiations for the Core Four also put Dubas in a difficult spot. To add insult to injury, the pick Dubas traded ended up landing in the lottery after Toronto’s 2019-20 season went off the rails and ended in a “qualifying round” bubble defeat at the hands of Columbus. Carolina got their hands on 13th overall and selected Seth Jarvis, who has since become an excellent player.
Another folly made around the same time was the trade of Nazem Kadri to Colorado. Kadri had been repeatedly suspended in the playoffs for dirty hits, and the common public sentiment was that he could no longer be trusted and must be traded for someone who could contribute in the playoffs. In spite of the baggage, Kadri was still a highly talented, gritty, and cost-controlled 28-year-old who played a premium position. Dubas dealt Kadri to Colorado in exchange for Tyson Barrie and Alex Kerfoot, a disastrous trade. The Leafs flipped a multi-time 30+ goal center who would win a Stanley Cup as a 2C in Colorado with three years left on his contract for a replacement-level, undersized, pass-first winger and a rental power-play specialist defenseman.
Those were major errors that further sapped Toronto of any quality depth around the Core Four, but I don’t want to make it out to be a total failure on the part of Dubas to accentuate the core. There were some big wins, including the trade for Jake Muzzin, who was a rock for the Leafs on the back-end. It did cost Dubas a first-rounder and Durzi, but Muzzin gave Toronto several great years of production. The addition of TJ Brodie, while not a world-beater, made the Leafs steadier on defense as well for a time. The aforementioned Frederik Andersen was generally strong in net, although with playoff hiccups. Dubas acquired Jack Campbell in a trade with Los Angeles, adding a cheap goalie who could fill in once Andersen’s Leaf career was beset by injuries.
But for the most part, it was on the Core Four (or five if you include Rielly) to deliver. The problems developing players (trading Mason Marchment for Denis Malgin didn’t help, either) and the contract picture that placed the Leafs tight against the cap meant it was on those key players to deliver.
Early playoff heartbreaks against Washington and Boston were painful, but some believed it would harden the Leafs’ core for the better. That belief began to fray after the team was stunned by Columbus in the 2020 bubble, but once the NHL announced that the Canadian teams would compete in the same division for the 2021 season — taking the Leafs out of the brutal Atlantic Division and giving them a clear path to the final four — hope and be-leaf began to rise again. Matthews, Marner, and Nylander were now aging towards their mid-20s, the peaks of their power. They just had to do it now.
What followed over the next five years was a hockey version of Waiting for Godot. If there is one line to sum up the Shanaplan and why it failed, it is that Brendan Shanahan went to his figurative hockey management grave believing that this core group of players were special, and every year they proved they weren’t when it mattered most.
Under both Kyle Dubas and the successor GM Brad Treliving, the Shanahan regime saw so many changes to the supporting cast. Jake Muzzin and TJ Brodie aged out, so Jake McCabe and Chris Tanev were brought in. The goalies changed, from Andersen to Campbell to Ilya Samsonov to Woll and Anthony Stolarz. Complementary top-six players changed, with Zach Hyman leaving in free agency, to be replaced by Michael Bunting and later, Matthew Knies. Depth forwards also changed; Ilya Mikheyev, Alex Kerfoot, and Pierre Engvall were replaced by the likes of Bobby McMann, Scott Laughton, and Pontus Holmberg.
The Shanahan regime tried different veteran leaders, signing Joe Thornton and Jason Spezza, and later adding Mark Giordano via trade. They made splashy win-now trades, bringing in Nick Foligno in 2021 and Ryan O’Reilly in 2023 in exchange for expensive packages of draft capital, hoping that those moves could lift them over the top. The Leafs went through three coaches to try and find a different mix: Mike Babcock, Sheldon Keefe, and now Craig Berube.
But the one thing that never changed was the core players, the Core Four plus Rielly. That was Shanahan’s abiding belief: Some combination of coaches and supporting cast would give the core what they needed to raise their game and take the Maple Leafs to the promised land, just as Shanahan himself had done alongside Steve Yzerman, Sergei Fedorov, and Nick Lidstrom in Detroit two decades earlier. The core never changing was the one overriding constant of the Shanaplan.
It’s not like there weren’t opportunities to do so. The first obvious one was after the loss to Montreal, when the Maple Leafs choked a 3-1 series lead to a team they were massive favorites over. The Leafs failed to start on time in either Games 5 or 6, before furious rallies sent the games to overtime, which Montreal won both times. Then, in Game 7, a timid start gave way to a lifeless effort and a 3-1 defeat, a late goal only serving to break the indignity of a Game 7 shutout.
The loss to the Habs was the most obvious sign that maybe this group didn’t have it. Maybe it was time for a change, to explore different possibilities of configuring the core. Some argued against it, suggesting it would be too reactionary to throw in the towel when Marner and Matthews were not even 25 yet. Shanahan and Dubas seemed to agree, defending the failure of the core in an offseason press conference, continuing to cement a culture that seemed to lack a degree of accountability. This would pop up again in later years, when even mild criticisms (or benchings) of core players by Sheldon Keefe were walked back and apologized for in short order. Or when Keefe attempted to cushion the blow of a playoff loss with “respect in the handshake line.”
The Tampa Bay series in 2022 that prompted Keefe’s infamous handshake line comment was so close that the one-goal loss in Game 7 was forgivable. Which is why 2023 is the moment, in hindsight (and to some, at the time), when change should have happened. Despite getting arguably outplayed by the Lightning, the Leafs finally won a first-round series by defeating Tampa Bay, ending the Eastern Conference dynasty. The Leafs were heavy favourites over Florida in the next round, and the Passion in the fanbase was at an all-time high. The curse was broken, and the deep playoff run was about to begin.
Instead, it never started. The Leafs were stunned on home ice twice by Florida and were completely unprepared for Game 3, hanging around a game they didn’t deserve to be in before losing in OT to fall down 3-0. They won Game 4 but were felled in Game 5 at home, ending their playoff run.
Faced with the big question of whether to more seriously consider significant changes, Kyle Dubas had until July 1, 2023, to trade Mitch Marner before his full no-movement clause kicked in. But just days after Dubas’ press conference, he was fired by Shanahan as part of a feud that remains somewhat murky to this day. Shanahan, in his most memorable “pulling back the curtain” moment, rushed to inform the Core Four as fast as he could that no matter who the new GM would be, none of them would be traded. To anyone who thought it was only Dubas behind the eternal defense of the Core Four, that moment in time should’ve revealed the real inner workings of the front office.
Brad Treliving replaced Dubas, and while the philosophy of roster-building around the Core Four changed, the defense of them did not. Matthews and Nylander were both extended during the first season of Treliving, and thus the Core Four would persist, now facing Boston in an odd series where both Matthews and Nylander missed significant chunks with injury, making the seven-game defeat more swallowable.
Even as late as the middle of this season, the defense of the Core Four continued, with Shanahan and Treliving tendering Marner a contract extension rumoured to be eight years in length and with a cap hit exceeding $13 million. Marner declined to sign such a deal, and now backed into a corner, management finally explored trading him to Carolina in exchange for Mikko Rantanen. Marner refused to waive his no-movement clause, and the trade never materialized.
It’s somewhat amazing to imagine a world where Marner signed the offered contract, if he had an eight-year deal yet to start after the 2025 Panthers series unfolded. Toronto surprisingly managed to go up 2-0 in the series and were up 3-1 in Game 3, only to lose three in a row, including an embarrassing blowout in Game 5. They rebounded in Game 6 to play a magnificent defensive game on the road and even the series, only to lay the greatest egg of them all in Game 7 on home ice back in Toronto.
Maybe the core was never the right one
As someone who follows and analyzes this team, I have spent many days thinking about all the what-if scenarios of the Maple Leafs over the past number of years, and how the years with this core could have played out differently. Many of the events mentioned in this piece are part of those thoughts. What if the Leafs had done a little better in those early drafts and had a home-grown defense corps to support the core? What if COVID hadn’t frozen the salary cap right when the Leafs most needed it to rise? What if the Marleau contract and trade hadn’t happened, and the Leafs hypothetically had Seth Jarvis on their team? What if the Leafs were in the Metropolitan Division and were handed easier playoff matchups early on, instead of repeated clashes with the greatest teams of the era?
I could go on forever about all the possibilities, but as time has passed, I have increasingly come to believe that none of these hypotheticals really matter. Why? Because this core was almost certainly never the right mix of players to begin with, and nothing could have changed that. Not when the problems are so repetitive and so deeply ingrained. That no matter what changes with the supporting cast, it is always the same story. Something far deeper and far more inherent to this specific group of players seems to be ailing them.
What stands out the most is how predictable it’s all become. So many Leafs fans predicted a victory in Florida in Game 6, when most outside observers felt the series was over, because the most Leafs way possible for this all to go was to win Game 6 and bring hope back to the fanbase, just to crush it one more time. Of course, this is exactly what happened. The problems year over year are so similar, none more obvious than the power play. No matter how good the Leafs’ power play is in the regular season and no matter how much salary they commit to the players on it, it can never perform consistently well for an entire playoff.
Indeed, time has felt like a flat circle in this Core Four era. The coaching and roster were always tinkered with, yet we’d get to the end of the season and conclude that the Leafs had never seriously tried other line combinations to break up Matthews/Marner if the going got tough. Most of all, we’d see the entire team fail to score at the end of a playoff series. Like clockwork, the Leafs were always capable of scoring early in a series, especially Marner, before the offense would inevitably dry up. From 2019-2025, the Leafs played in six winner-take-all games (Game 7s, or Game 5 in 2020) and scored one or zero goals in all six.
Brendan Shanahan always believed in Marner, Nylander, and Matthews manufacturing one dominant playoff run where they put it all together and rewarded his faith. History will show that he was wrong in his belief. It’s hard to know why, other than acknowledging that there are great players throughout NHL history who struggle to elevate their games in the playoffs. Joe Thornton may be the most famous, but similar discussions have followed everyone from Paul Kariya to Artemi Panarin to Tony Esposito. It’s hard to pinpoint why other than to recognize it as an absence of greatness in the big moments, as Justin Bourne put it in a good piece last week.
Maybe Mitch Marner was never a good fit to play in his hometown, too aware of/affected by the pressure. Maybe Auston Matthews is too laid back off the ice to have the killer instinct on it. Whatever the reason is, these players have been consistently unable to elevate their games to deliver the superstar playoff moments, the kinds that Leon Draisaitl and Connor McDavid have delivered on past runs for the Edmonton Oilers, or the ones that Rantanen has delivered for Dallas this playoffs. They haven’t taken over a playoff series, or even a game if it’s later in the series. Their games become too timid, too defensive, and they need others to carry the mantle instead.
Occasionally, that has been Nylander, but not consistently enough. In reality, there is no one else to carry the mantle because these core players are the team’s stars. Your best players must be your best players to win the Stanley Cup. Since the Leafs’ cannot raise their game to play elite hockey in the playoffs, maybe they are players who needed to be the stars on a team with three strong lines, an iron-clad D core, and a star goalie in order to win a Cup.
If that is the case, maybe someone should have told them at contract negotiation time that there wouldn’t be any cap space left to build the necessary depth. That is the ultimate irony of the Core Four era: the salary structure necessitated by the bloated contracts they squeezed the Leafs for put even more pressure on the shoulders of players who couldn’t handle the pressure. And thus the final memory of the Core Four era is of that team losing to a Florida squad built around immense depth, thanks to star players signed to below-market-value contracts — a team that made bold, core-altering trades along the way. One could say a culture of winning won out over a culture of losing.
Ultimately, the culture of losing was built by a team president who believed up through his final days on the job that this group of players he drafted would deliver. It turns out they couldn’t. Shanahan went out of his way to protect the core from consequences when they messed up in the playoffs. He coddled them far past their infancy in the league and shielded them from public accountability. Shanahan placed all his trust and belief in Marner, Matthews, and Nylander. They ultimately repaid him for that belief by likely handing Shanahan his walking papers.
I suppose it’s a cautionary tale in making sure the players you’re drafting have their heads on right; that they’re good fits to play in the market, while recognizing the difference between the regular season and playoffs. And a lesson that simply drafting uber-skilled players who produce in the regular season does not guarantee that a Stanley Cup is in your future. It’s a story of failing to adjust your priors as new information came along, that maybe the fabled core of your team isn’t all it’s cracked up to be. A story of a team president so focused on sticking to a plan and not being a reactionary that he failed to react at all.
Whatever it was, it’s the final page of a peculiar epic with little parallel in NHL history. A nucleus of players so promising and talented, but who didn’t have the winning juice, so to speak. You could argue that the greatest sign of all that the Toronto Maple Leafs are cursed is that only they could draft two of the most talented players in franchise history, just for them to turn into the two biggest playoff underachievers of their generation. Of course, it wouldn’t have hurt to build around them a little bit better.
Now, all that is left is the empty feeling in Leafs Nation. The knowledge that the Stanley Cup will never come to Toronto in this form. The faded memories of the joys of the early Matthews/Marner era, when they were a band of young pups exceeding expectations, and fans were blissfully unaware of what was to come next. The Core Four and the Shanaplan, as we knew it, are likely finished, the most underwhelming chapter in the franchise’s century-long history. One long on raw talent that even the Pat Quinn teams lacked, yet so short on heart and fight.
We don’t know what comes next, although some members of the core will still be around to lead the next iteration of the Toronto Maple Leafs. Hopefully, they will have more of the dawg in them that this bunch lacked. Hell, it’s hard to have less.
