The Trade Deadline has now passed, and while the Leafs did offload Nic Roy, Scott Laughton, and Bobby McMann for a 2027 first, 2027 second, 2026 fourth, a conditional 2026 third, and a conditional 2026 fifth, they are still in a brutal position. They’re too good to tank, too bad to make the playoffs, too draft-pick poor to rebuild, and too prospect poor to make an impact. The Leafs are in purgatory. Let’s break it down
How did the Leafs end up in purgatory?
In a perfect world, the NHL is cyclical. Teams go from being very bad and drafting well to getting better as those players do well, to competing with their core players, then those players get older, and the core starts to break up, and the team gets worse before bottoming out and needing to rebuild again.
This isn’t how it always happens, with teams pushing their window open as long as they can to get maximum playoff game revenue. At some point, they get less competitive and then have to rebuild. Often this is a slow, gradual decline, with teams not pushing all of their chips into the middle year after year, and starting to add draft picks and young players to their group.
For the Leafs, this decline went like a rock in water, falling straight from the second round of the playoffs to being out of the playoffs this season. Losing Mitch Marner was a big part of the decline for sure, but frankly, this team’s roster construction last season and this past summer under Brad Treliving left a lot to be desired. The team got bigger and heavier, but they also got slower and older. The plan was to build a better playoff contender, but that doesn’t matter if you’re not a playoff team.
A salary cap structure built for the playoffs, destined for a rebuild
The Leafs cannot look themselves in the mirror and say this was a down year, despite what Keith Pelley said to season ticket holders. This isn’t a one-off; this is a structural issue. The team desperately needs to tear down and rebuild, but their contracts and salary cap structure are built for the playoffs.
The team has four players making more than $7M per season for at least the next two seasons. While Auston Matthews’ contract is just for the next two seasons, it’s at a whopping $13.25M, making it nearly impossible to move on its own. The contract also comes with a full no-movement clause and is almost entirely signing bonuses, making the deal virtually impossible to move.
There’s almost certainly no market for Morgan Reilly, and basically nobody has the cap room to take on a long-term contract for William Nylander, on top of his full NMC and bonus-laden contract. The only player they could move is Matthew Knies, but even then, do you really want to move your one really good young player to take a gamble on draft picks? Unlikely.
Then there are so many older veterans on longer-term deals that the Leafs are going to struggle to get out from under. John Tavares, Jake McCabe, Chris Tanev, Oliver Ekman-Larsson, and Max Domi are all over 30 and signed for at least the next two seasons. Some will have value as rentals in the final year of their contracts, but it’s hard to see a playoff team wanting any of these players with term, given their age.
Taken together, the Leafs are in a tough position. Their contract structure doesn’t allow them to effectively tear it down right now. Their assets are either too old, too expensive, or without value. That’s problem number one.
On paper, the Toronto Maple Leafs aren’t a playoff team, but they aren’t a bottom-feeder. They’re in purgatory
The Leafs with this roster are a fine team. They have several elite pieces in the lineup. In a perfect world, Auston Matthews should be a top-five player in the league. William Nylander has been a top-20 player in the league, even this season. Matthew Knies is a fantastic young player with a lot of skill and upside. He could get even better.
The problem is that this team’s roster construction has been flawed. There continues to be not enough strength down the forward group, with Mattias Maccelli and Dakota Joshua expected to be that depth. The team didn’t give Nic Roy long enough to prove he was the playoff performer that they were promised, but getting a first-round pick back was worth more in a down year.
Beyond that, the team didn’t utilize Scott Laughton on the wing to get more out of Matthews and Nylander, playing him instead in a depth centre role. They did get a good amount of production out of Bobby McMann before they moved him, but there always felt like there was a little more to give with him.
They’ve started to really tank, but might already have too many points on the board. They still sit 24th in the league with 65 points today. Looking at the teams behind them, it’s going to take a lot for this team to end up at the bottom of the standings this season, or even end up with a top-five pick, unless they win the draft lottery.
This is a major problem, leaving them in purgatory. With their draft picks, they will continue to get decent role players in the middle of the draft, with some being potentially top-six forwards or top-four defencemen. However, the true elite talent that they need will continue to elude them.
The Toronto Maple Leafs are nearly out of draft picks
While the Leafs did get a first-round pick back next year, it’s from Colorado, meaning the pick is likely a very late first-round selection. You’re not getting much in the way of elite talent from a pick that late in the first round.
Beyond that, the team is out two of their next three first-round picks, between the Brandon Carlo and Scott Laughton trades. While there is some protection should the Leafs finish with a top-five or top-10 pick, respectively, it only delays the inevitable that two first-round picks are out the door in the Leafs’ rebuilding era. That’s really bad news.
They are also out a second-round pick next year, a third in 2027, and a fourth next year and in 2028. It really is death by a thousand cuts.
The Toronto Maple Leafs’ prospect pipeline is empty
Looking backwards, the Leafs have been competitive, meaning they have been trading their picks away from strength at the time, but even with the picks they had, they couldn’t get much value. Since the Matthews draft, the team has had six draft picks play more than 100 games in the NHL: Timothy Liljegren, Rasmus Sandin, Sean Durzi, Pontus Holmberg, Nick Robertson, and Matthew Knies. Only one of those players is a top-six player, and that’s Knies.
The team has made 17 picks in the last three drafts, which, on paper, is nearly the full seven per season. The problem is that there are two first-round picks, one second-round pick, one third-round pick, and one fourth-round pick. Twelve of the 17 picks are in round five or later. Those are real lottery picks, with few, if any, projected to be NHLers. At that point, you’re hoping to get lucky, not actually having a strategy.
The lone exception in there is first-round pick Easton Cowan, who looks to be a heck of a player, but to go 1/17 is really brutal odds. But he’s already in the NHL, with 48 games under his belt. He’s not going to be considered a prospect by year’s end if he keeps playing.
You may get games out of Ben Danford, and don’t count out Tinus-Luc Koblar, but the rest look like swings and not hits.
How do the Toronto Maple Leafs get out of purgatory?
Frankly, it’s probably going to get worse before it gets better. This isn’t going to be like the 11 drafts between 2006 and 2016 inclusive, when the Leafs had seven picks in the top half of the first round, including Matthews, Nylander, Mitch Marner, and new member of the Colorado Avalanche, Nazem Kadri. Expect the next three years to be painful as the team begins to slowly bottom out.
Then the team will likely need to actually rebuild around 2029 or 2030 for a few years before turning it around in 2032 or 2033.
In there, the team will need to make some tough choices around the future of Matthews, Nylander, and Knies. Being able to move them for a package of picks and prospects would do wonders to speed this up, but with the way the first two contracts are structured, it’s hard to see that happening.
The other part is whether GM Treliving is even the right man for the job. Having steered the Calgary Flames firmly into a death spiral from a playoff spot, it’s time the organization part ways with the son of the founder of Boston Pizza. His moves and inability to derive real value from this trade deadline should be enough to send him packing.
There needs to be a reset and understanding in the organization. They need to reset on what they are and come to a common understanding about their future. This team needs to prepare for pain, begin the tank, and start to build a new core.
The only way out is to begin again. Invest heavily into a couple available GM level execs. and half a dozen new head scout quality advisors. Get rid of Pelley and Treliving. Tank this year by using as many prospects as we can find. Including overseas. Demote everyone we dont need including Mathews. We developed a core with 4 high 1st round draft picks. Let’s get 5 or 6 good picks from trading the core and finishing last for a few years. Watch prospects for a couple years. And cut the prices of tickets by half until you’re relevant again.
Where are you going to put all the players on the roster and in the lineup now? Are you going to put Matthews, Nylander, Knies, Maccelli, Robertson, Tavares, OEL, McCabe on waivers?
I’m not buying into the entirety of the gloomy picture depicted here but do concede that things are not looking great at the moment. However, one aspect of this team that is often overlooked is that this is a squad that can be improved, however marginally, by simply subtracting bodies.
There are also some trade assets that could be returned by a goalie trade, possibly even before the draft.
After the draft how about reducing the list of smallish left shooting players from four to just one? Keep a still developing Easton Cowan but don’t qualify pending RFAs Nick Robertson and Mattias Maccelli, then buy out Max Domi. This is as a worse case scenario if one or more of these players cannot be dealt for even modest returns but the goal has to be to free up the roster spots they currently occupy. Then ship out one of either Steven Lorentz or Dakota Joshua.