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.
The observation about the poor job that Hextall did and the 1st year of Dubas in Pittsburgh misses the rumors that ownership meddled and dictated quite a bit of that. It was also rumored that they blocked moves at the end of JR’s time in Pittsburgh and a reason for why he quit. When these anonymous rumors are repeated across 3 GMs, perhaps the rumors should be believed.
FSG spent a ton of money on the team and wanted to enjoy a winner instead of rebuilding, while being judicious on spending. It was only after multiple years of failing at competing and when the need to rebuild was obvious did ownership allow for it.
Since Pelley and MLE appears to be acting the same as FSG, the Penguin failure arc seems to presage Toronto’s future.
They started losing 1 or 2 games too late. With the 5th draft slot before the lottery, the pick will likely end up with Boston. The Panthers did a better job ensuring they were in the top 10 and keeping their pick by having Barkov stay out all season. Somehow he’s now able to play for Finland in that tournament though.
One thing alot of failing clubs need to change is, STOP HIRING FORMER PLAYERS WITH ZERO EXPERIENCE FOR EXECUTIVE POSITIONS.
Yes, hire me, not a former player with zero experience. I’ll do my best. Promise.
Spezza for GM
Sundin and Gary Roberts AGMs
as a fan of the other 31 teams that would be great!
Give us Ivar please. We have the Swedish connections.
Even when they suck, it’s all about the Maple Leafs.
Excellent article. Thanks.
Caps and Pens both managed to find coaches who took seemingly hopeless rosters into the playoffs. But that’s as far as it went. No coach would win the Cup with these rosters. So is it even worth trying to go this route?
It’s better to admit that the window of opportunity has closed on this roster and start a full-blown rebuild. This situation presents an excellent opportunity for that:
1. Both Matthews and Nylander are at the peak of their value and will fetch a nice starting capital of futures.
2. The current situation around the team is so bad that both will likely wave their NTC’s.
3. With all retention slots available, the Leafs should be able to buy more futures by retaining on these players.
4. Weaponizing the available cap space can buy even more futures.
For this strategy to succeed, it is crucial to take no prisoners and avoid half-measures. Everything and everyone should be made available at the right price.
I agree. It’s rare that a team that looks like it needs a rebuild has a superstar & another star player in their prime that can be moved. The leafs are in a good spot if they decide to go that route.
That’s a vast amount of “ifs,” though. There’s no indication whatsoever that Matthews or Nylander are inclined to wave their NMCs, twelve teams have more cap space than Toronto does this coming season (six with more than $30 MM free), and “futures” only work if they turn into legit NHL players.
Goals sell merch. Defense is an omnishamble and they haven’t had a franchise goalie since Felix Potvin.
Belfour, Cujo, and Andersen were excellent goalies
They were screwed when Shanahan wouldn’t let Dubas trade Marner before his NMC kicked in. Running back the same four that ate up half their salary cap was clear that it wouldn’t work before they came to that deadline.
Canucks say, hold my double chi latte
The Leafs has big big big problems. They seem not able to focus on playing hockey and most importantly compete with other clubs , I call them the champions of distractions.
There’s always something off Ice going on that deminishes the overall team gameplay. Coach pointing fingers at players by name after a loss is really not helping. There’s so many things they are not doing well, the worst I think is the Political shaming the fans gave to Austin Matthews after winning gold medal. It’s that kind of things that is very destructive for the team chemistry. This team is ready to blow from inside out at any time given. The fans and management are at fault. It’s mindset issues.
The draft lottery?…Lol! It wouldn’t surprise me if Toronto ends up in the top 5 in the draft so they don’t lose their pick to Boston. It’s not a lottery really. Let’s be real here, everyone (or at least should) know the so-called “lottery” is practically rigged as the NHL will dictate who ends up where in the draft order when it comes to teams outside the playoffs.
As for Toronto itself, that organization has been a mess for some time. It’s not going to change anytime soon. The organization, the management, the culture, and list goes on are just inefficiently eroded and toxic. No organization needs more of an overhaul than Toronto in practically every aspect.
You truly believe the lottery is “practically rigged…”? Why would you even continue being a fan if that were the case? Why are you ok with the league rigging it? You’re a good guy, I’m not trying to be snarky. I just can’t understand how you believe this with no proof whatsoever.
It will never be mentioned but this is one of the worst run franchises in all of sports. Money means nothing if you do not spend it properly
Just like the Cowboys. Of course they would never be mentioned as a poorly ran franchise as they are a crown jewel
Sadly this is the only team that has its very own show on NHL Network radio on Leafs Lunch. Also worst fans in the sport. According to them. Every player wants to sign there. All the other players will get traded there for a 7th round pick in 2056.
Sadly players are not stupid. Not many who get UFA status say. Hey honey. Let’s move to Toronto so the media can follow us around. The fans can bother us whenever we go outside and god forbid we lose. Sounds great right
There are so many players with the Leafs on the NMC/No Trade lists.
I know the actual organization takes excellent care of the players but when the media and fan base is the issue what can they do.
Matthews is gonna bail as soon as he can. The Leafs are holding back his true talent But of course he cannot be considered a generational talent because he is not from Canada
Toronto will have to share the short bus with Vancouver.
” … would it even make sense at this point to add to a core group of players who have won exactly nothing in ten years …”
Y’know, if we apply that standard, then four-fifths of the league suck. Only seven teams have won Cups in the last ten years. Eighteen teams haven’t won a Cup in twenty years or more. Eleven teams have NEVER won one.
Yep, Toronto had a suckass year, no error. But describing this as a franchise that’s Uniquely! Ruined!, after coming off a five year stretch averaging 50+ wins per 82, just strikes me as the same hyperbolic “Scotiabank Arena is the center of the hockey universe” garbage that’s the REAL millstone hanging around this team. A number of teams would gratefully accept such a terrible long term record.
Do they have roster problems? Yes. Have they handed out way too many NTCs/NMCs? Yes, although that seems to be a disease spreading league-wide. Is it an aging team? Yes, although it’s tough to claim that the likes of Tavares or OEL were the problems this year.
But it seems that the biggest problem the Leafs have is morale, and the crushing weight of expectation under the microscope. NO trade’s going to solve that, NO winning streak, NO top-shelf goalie. I’ve long wondered whether the smartest thing Leafs ownership could do is publicly welcome a second team in the GTA: Hamilton, York, Mississauga, wherever, just to ease off on that terrible perpetual spotlight.