The headlines about the Maple Leafs over the past 12 months have been largely negative, and for good reason. The team hasn’t been good since being knocked out of last year’s playoffs in the second round, and they’ve been a circus off the ice as well.
But a team that just a few years ago had quiet, steady confidence has become a tsunami of chaos wrapped in a corporate blanket. The Maple Leafs are in trouble, not the kind that can be “fixed” in a season or two – as we’ve seen in Pittsburgh or Washington – but the kind that can lead to a decade of futility.
Before diving too deep into the rabbit hole, a quick caveat. If the right lottery balls fall and Toronto turns this boondoggle of a season into the first overall pick, Gavin McKenna, then all the points that follow could become moot.
However, if the lottery balls fall the other way and Toronto ends up with a non-top-five pick that will be sent to the Bruins, it would lead to a more disillusioned fanbase and more toxicity around an organization that has watched a once-promising rebuild completely unravel in just a few years.
Some might argue that it all came apart in the last 12 months, and there is a good case for that, given that Toronto saw its biggest year-over-year point decline in 109 years. But the truth is that the seeds of this tree of woe were planted years ago, and they’ve been soaking up water for the last couple of seasons, only to emerge as the Maple Leafs’ first playoff absence in ten years.
The issue for the Maple Leafs isn’t a single item on a checklist. It’s a systemic issue that has filtered down from the top and has culminated in this week’s news from The Athletic that Maple Leafs Sports and Entertainment president Keith Pelley has become deeply involved in roster construction, something he’d never done before.
The Athletic piece (subscription required), written in partnership by Jonas Siegel, Chris Johnston and James Mirtle, delves extensively into the Maple Leafs’ past season and pulls no punches in its depiction of their fall. History is littered with empires that fell, but for the Maple Leafs, the empire they were supposed to become when they emerged from a rebuild ten years ago never materialized.
How they turn things around at this time is incredibly unclear. There is perhaps only one quick fix: the aforementioned McKenna lottery ball going their way.
Outside of that, the road back to relevancy is paved with speed bumps, and at the moment, there isn’t an obvious candidate in the organization who can lead them to the promised land. There isn’t exactly a litany of candidates outside the organization, either, who could undo all the damage that’s been done to their roster.
Lots of names will get tossed around, but there aren’t many free-agent managers available who have built perennial Stanley Cup contenders, with the exception of Stanley Cup winner Peter Chiarelli, who is probably not high on Toronto’s list of candidates due to a litany of other roster construction blemishes on his record
Some have mentioned Mark Hunter of the London Knights as a potential candidate to take over, but Hunter had a somewhat sour experience with the Maple Leafs earlier in his career as an assistant GM, passed over for promotion in favor of Kyle Dubas, and may not want to leave the stability of the OHL Knights for the chaos of the Leafs. However, money can heal a ton of wounds, and if Toronto wanted to, they could probably find enough to mend fences with Hunter.
That is what Toronto will have to try to do if it wants to turn its current luck around in a hurry and flex its financial might. There is no cap on management, scouting, and player development, and it is an area where Toronto could invest heavily again to quickly retool or rebuild its roster. However, based on the story from The Athletic, it appears that Maple Leafs ownership has plans to move in the opposite direction, though they might not have a choice given the state of their roster and prospect pool.
When Toronto’s lineup is fully healthy, it’s not exactly a group that will strike fear into many opponents. There are significant gaps throughout, and not much toughness to speak of.
The biggest hole is on defense, where the team lacks a true number one defenseman who can run the power play, kill penalties, and play a solid two-way game at five-on-five. Many fans hoped Morgan Rielly would fill that role, but his game is all offense at this point, and that offense has been drying up in recent years.
The good news for Toronto is that they have plenty of cap space this summer ($22.2MM, with just three roster players to sign, per PuckPedia). However, the bad news is that there isn’t much available in free agency, and Toronto doesn’t have many draft picks or prospects to trade.
There are a few future pieces they could deal, but would it even make sense at this point to add to a core group of players who have won exactly nothing in ten years and have now gone through several management groups with almost no variation in results? The constant during that time has been Auston Matthews, William Nylander, and Rielly, who have all been on this ship while the deckchairs have shuffled around them year after year.
Is it time to move one of them? Can Toronto even move any of them, given their contracts, no-trade clauses, and last season’s struggles?
The core players have said they want to run things back in Toronto and give it another shot, which seems foolish at this point, given the track record. A new GM who comes in and tries to build around Matthews and company could be in for a fool’s errand, throwing good money after bad as they fall victim to the sunk-cost fallacy.
Make no mistake, every GM falls victim to it, throwing good assets out the window to undo previous errors. It usually doesn’t end well and can ultimately lead to a reduction in the contention window, which is exactly what happened in Toronto and elsewhere.
Many teams have done this before, burning through draft picks and prospects in pursuit of a playoff berth, only to miss and have nothing to show for it. The Penguins notoriously let Ron Hextall burn through assets in an attempt to save his job in 2023.
He traded a second-round pick for Mikael Granlund, who had the worst run of his career in Pittsburgh before the Penguins missed the playoffs. Hextall was fired shortly after the season, and Dubas came in and immediately made the same mistakes as Hextall, trading good assets for aging ones, before realizing his errors and pivoting to a retool.
Dubas then systematically moved out the Penguins’ veterans who didn’t fit the plan and moved on, recouping tons of young assets in the process. He also took on bad contracts along with draft picks to help teams that were strapped against the cap.
Some might look at the Dubas strategy and think it could work for Toronto, and who knows, maybe it could. But the issue is that it took Dubas two years to see results from those moves, and we haven’t fully seen those results yet.
Many of the draft picks Dubas acquired are in upcoming drafts. That strategy takes time, a lot of time, and time is something Toronto doesn’t have, given that Matthews has just two years left on his deal now.
Another issue for Toronto in deploying the Dubas strategy is that there simply aren’t as many teams up against the cap as there were a year or two ago, when Dubas made his moves. This means teams may be more inclined to simply bury bad contracts rather than trade them for an asset to get rid of them.
It was still painful for Pittsburgh, as they missed the playoffs for three straight years before making it this year. Retools take time; even when most of the moves work out well, there is no quick fix, only trade-offs. Toronto’s management has to decide which trade-off they are comfortable making before making management hires and pointing this team in a different direction.
Whatever direction is ultimately chosen, the road will be bumpy, but any team that finds success has to endure adversity, some more than others. And for the Maple Leafs, if they do eventually find success, they will have endured more adversity than any other team.