Evaluating the moves Brad Treliving did and didn’t make in his first trade deadline as Maple Leafs GM

The trade deadline has come and gone. While it wasn’t earth-shaking, the Maple Leafs took a swing at addressing their two biggest needs: the defense and the penalty kill.

On defense, the Leafs not only lacked right-handed options – Timothy Liljegren was their only regular right shot – but they lacked quality, top-end players. Related to the personnel issues on defense, Toronto’s penalty kill has been an Achilles heel all season. They currently possess the worst penalty-kill ranking of any team in a playoff spot.

Every team can always benefit from additional quality on their team – look at Vegas acquiring Noah Hanifin even though they returned their Cup-winning defense from last season – but in terms of the holes that absolutely needed to be addressed in some capacity by Brad Treliving, the defense and the PK were the top two, especially for a team lacking in draft capital and hesitant to trade its top prospects.

In total, the deadline movement saw the following assets and players move in and out of the organization:

It’s not the most exciting group of additions, but this also wasn’t the sexiest of trade deadlines in general.

The defense market

Let’s start with the right-handed defense need.

Ilya Lyubushkin fits the bill, but he’s also not a needle mover, which anyone who was a Leafs fan a few years ago could tell you. There is a comfort level with the player, the coach, and his partner (which isn’t nothing). The transition has been seamless to this point – he has been solid through three games – but we’ll see how it goes in the playoffs, where Lyubushkin showed cracks the first time in Toronto.

We spoke about Chris Tanev at length over the past few months, and while I think his fit would have checked every box (right-handed, big matchup minutes, penalty-killing ability), Nick Kypreos noted this week that the Leafs’ first-rounder was on the table and Calgary went with another offer.

If the first was offered and Calgary wouldn’t accept it, I don’t think Treliving could justify upping the ante further for a 34-year-old pending UFA. If, on the other hand, the Leafs wouldn’t offer up their first, it’s fair to question the decision-making process given how well Tanev fit their needs and that the Leafs instead packaged a collection of other draft picks to acquire two less impactful defensemen as part of a defense-by-committee approach.

Outside of Tanev, the list of other right-handed defensemen who moved is underwhelming:

• Sean Walker
• Matt Dumba
• Troy Stecher
• Erik Johnson
• Andrew Peeke
• Collin Miller
• Chad Ruhwedel

I have a difficult time looking at the above list – especially after the Avalanche traded a first-round pick for Walker – and thinking there was a missed opportunity on it. Toronto needed to bring in a right-handed shot – five left-handed defensemen is not palatable at playoff time – and relative to the market, Lyubushkin is a reasonable add. Given the fit, their needs, the built-in familiarity, and the acquisition cost, I’d argue he made the most sense.

My right-handed defenseman of choice as a potential value add, Alex Carrier, remained in Nashville. The other right-handed defenseman of note who was potentially on the trade market, Colton Parayko, comes with six years left on his contract for a player turning 31 this year. He’s a nice player – and I can see the argument – but I can’t wrap my head around taking the contract on at his age and attaching it to a core still in its 20s. If it worked, Treliving would look like a genius, but if it didn’t, it’s the type of crippling contract that causes a franchise serious problems. With where their team sits today, I don’t think the Leafs needed to take that risk.

The right-handed market being what it was, the Leafs eventually turned to simply adding a defenseman in general and traded for the left-handed Joel Edmundson. We talked about it when they acquired him, but a big question mark with Edmundson is his health and the amount of gas left in his tank. He is only 30, but he has battled back issues to the point where surgery was on the table. He finally appeared to be on the upswing health-wise when he was traded in the offseason only to fracture his hand in a training camp scrimmage. He played his first game of the 2023-24 season on November 18.

Before his injuries, Edmundson was an effective defenseman capable of handling real responsibility. He was a regular – as a third-pairing guy – on the Cup-winning Blues in 2019, and he played over 23 minutes per night during the Habs’ Cup finals run. In his last fully healthy season – the COVID bubble year – he averaged over 20 minutes per game with a 54.28 percent shot share at 5v5 and Montreal outscored its opponents 45-27 with Edmundson on the ice.

It was the best season of his career, but then injuries derailed him. If he is healthy and able to adjust quickly enough in Toronto, he can be an asset. Joining a bad Capitals team a month and a half into the season and playing on the third pair while Washington prioritized their young left-handed defensemen – Rasmus Sandin and Martin Fehervary – as well as their defensemen under contract longer term (John Carlson, TVR, and Nick Jensen) is fairly irrelevant.

Heading into the deadline, a healthy Leafs defense shaped up like this:

Rielly – Brodie
Benoit – McCabe
Giordano – Liljegren
Lagesson

Coming out of the trade deadline, it appears to be something along the lines of:

Brodie – McCabe
Rielly – Lyubushkin
Edmundson – Liljegren
Benoit

It’s not a great defense, but it’s at least more logically built and the team has options. They could reunite Brodie-Liljegren, Rielly-Brodie, or Benoit-McCabe at any point. It’s going to be defense-by-committee, and it will be on Sheldon Keefe and Mike Van Ryn to find the right mix among the group of seven.

Outside of Tanev, the only other impact defenseman who was traded this deadline was Noah Hanifin, who wanted to return to the United States. There’s not much the Leafs could do about that one. Jakob Chychrun didn’t move, either, and neither did Adam Larsson or Jamie Oleksiak.

If they couldn’t pursue Hanifin with any chance of signing him and the first-round pick wasn’t accepted for Tanev, the Leafs were left with these types of options. We can quibble with who they opted to acquire, but there were only so many possibilities to choose from. The blue line is patched together for the time being, and Brad Treliving will have to properly address it in the 2024 offseason instead of taking a flier on a John Klingberg type as he did last summer.

The Connor Dewar acquisition

At forward, Treliving added Connor Dewar, a prototypical fourth-line forward who is a good checker and penalty killer. He’s also only 24 and is an RFA this summer, so they own his rights beyond the end of the season.

After an October 29 loss to the Nashville Predators, Sheldon Keefe said, “In a lot of ways, we are trying to manufacture penalty killers here. We are giving guys opportunities that they haven’t had before, whether it is Knies — who is new to the league — or other guys we have talked about who haven’t killed a lot. It is going to take some time.”

To this day, the Leafs are still trying to manufacture penalty killers. In the last game in Boston, Bobby McMann was seeing regular penalty-killing time. Pontus Holmberg has been a part of the units lately. They have more or less been forced to give Nylander and Matthews penalty-killing shifts.

In the offseason, Treliving didn’t bring in anyone who could penalty kill at forward. He signed Domi and Bertuzzi while promoting young forwards Knies, Robertson, and Holmberg. The lack of experienced options has been felt all season long on the PK.

I like Dewar’s speed and ability to disrupt plays on the PK, and as a forechecker, he brings some jam at five-on-five. If he can pick up the Leafs’ PK system (which has been successful up until this season) and help the team trend in the right direction shorthanded as a regular PKer, the acquisition cost of a fourth in 2026 and Dmitry Ovchinnikov isn’t worth second-guessing for a moment. It would also make Dewar more than a mere depth addition; the penalty kill is a fundamental issue that will be difficult to overcome in the playoffs if this continues.

As always, it comes down to the stars 

If the Leafs can push the penalty kill to a respectable level and the defense can be cobbled together into three reasonable pairs, this team’s fortunes are really going to come down to the same group of core players as always.

There’s only so much we can debate about the Leafs’ three NHL roster adds. Can they plug holes in the defense, offering upgrades over what they already had? Can they help the penalty kill (Dewar included)? If so, Treliving didn’t give up much to do it. If not, it’s a waste of picks, even if they are mid-to-late rounders. But most of it is futile if the top guys don’t deliver anyway. We all know they heavily lean on their top forwards in ice-time and salary cap allocation.

The idea that because Matthews is pushing for 70 goals in the regular season, the Leafs should throw all inhibition to the wind and sacrifice significant future assets to try to win this year is a bizarre notion. This kind of thinking seems to ignore that these core forwards have enjoyed amazing regular seasons before only to come up empty when it matters most.

We just came off a week featuring two rivalry games in which David Pastrnak outplayed all three of the Leafs’ top players by a significant margin in both contests. The Leafs aren’t adding more players of the upper-echelon calibre now. They are adding players to help support that calibre of player, and if the stars come up empty, it’s all moot.

More good players certainly help their odds, but it doesn’t mean much if the big boys shrink. We saw this movie play out last spring after the Ryan O’Reilly acquisition. This year, Tyler Toffoli is a really good player and would have helped – so is Elias Lindholm – but again, none of it really matters if the big guns are no-shows.

The Leafs aren’t asking their top guys to carry it all on their own. There are legitimate contributors on this roster who can support the stars if they rise to the occasion and lead the way. The coaching staff should be able to assemble four solid forward lines and three respectable defense pairings. They also have three goalies, one of whom stole them a playoff series last spring.

The Leafs’ power play, led by their top players, has routinely let the team down in the playoffs. They are clearly taking steps to address the penalty kill, but we will see if the attempted improvements actually pan out.

If Treliving failed to address the penalty kill adequately and it continues to haunt the Leafs throughout the playoffs, it is a failure on his part. If the defense is so weak that they cannot rotate through three pairings and set the table for the high-scoring attack, this would also be a failure on Treliving’s part.

Otherwise, all eyes are on the stars and whether they can finally slay the dragon with a dominant playoff run.

Final notes on the Leafs’ trade deadline: Treliving holds onto his top futures, Edmundson’s experience, the loss of Lagesson, and the physical factor

–  Fans have lived the history and failures of the team for years – if not decades – but Brad Treliving walked into the job ahead of a 2023 draft in which the Leafs owned a total of three picks. In the next three drafts, he doesn’t have any second-rounders or his first in 2025. The Leafs have put together a good but not great season so far, and the trade deadline saw a bunch of rentals move without new contracts in place with their new teams (Guentzel, Hanifin, Tanev, Lindholm). I think it’s pretty reasonable for Treliving to hold on tight to his first and top prospects given the circumstances.

–  Since the 1989 Calgary Flames won the Stanley Cup, no NHL team has won a championship without a previous Cup winner on the roster. Experience is an important asset in some capacity. Joel Edmundson is the only player on the Leafs’ roster who has won a Cup, and it is handy to have players with experience in those high-stakes situations. Luke Schenn was much better than people expected, and if Edmundson can provide anything along the lines of what Schenn contributed, it would be a very welcome addition.

–   I would have been surprised if William Lagesson cleared waivers. He’s put together a respectable season, has shown he can play on the left and right side, has flashed a little jam and penalty-killing ability, and he’s still only 28 years old. It turns out he didn’t make it past the third-worst team in the league in the waiver priority order (and I would wager a few others filed a claim as well).

He’s a serviceable NHL defenseman, and as Treliving noted when he acquired Lyubushkin, a team simply can’t have enough of those. That said, for this loss to be felt, the situation on the blue line would have to really spiral. There were at least eight defensemen ahead of Lagesson when healthy, and arguably, Conor Timmins is as well by virtue of his right-handed shot. Lagesson was either ninth or 10th on the depth chart.

The pending unrestricted free agent will go down as a minor footnote on this team’s season, but when they battled a collection of injuries in November, Lagesson stepped in and helped calm the waters. It was only a few weeks ago that he was pairing off with Morgan Rielly. It would have been nice if he remained in the organization, but the Leafs more than got their money’s worth on their bargain-bin summer signing.

–  Most of the trade action happened in the West this year. In the East, it has been the same group of buyers every year for the better part of a decade, and it shows in how few of them owned real trade assets to play with this year. The Panthers have made the playoffs for four straight years. Seven for the Bruins. Six for Tampa. Seven for the Leafs. Five of the last six years for Rangers. Five for Carolina. Buying every year catches up to a team eventually.

–   Much has been made about the Leafs adding several physical players, but it’s worth noting the opponents they are likely to square off against in round one, be it the Bruins or Panthers. A certain level of physicality and violence is required against these teams. In just five games against the Panthers last playoffs, Bennett ended Knies’ season, crosschecked Bunting in the head, and ran Tavares. Tkachuk rabbit punched Marner in the face repeatedly, and Kampf got hammered by Gudas. There was no response at any point from the Leafs.

There were many reasons why the Leafs lost the series, but Florida’s physical bullying was one of them. Toronto is better equipped to handle the physicality this spring and probably even initiate some of it rather than always being the reactive party. Again, though, it’s still the same players at the top of their lineup, and we’ll see how much of a difference this makes.

Further Listening: In the post-trade deadline edition of the MLHS Podcast, Nick Ashbourne and I discussed Brad Treliving’s first deadline as GM of the Maple Leafs and the recent losses to the Bruins.

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