Leafs trade wishes ahead of the deadline — The Fourth Period

As you know, this is my Christmas, my favourite time of the year. Which brings back so much joy, so many memories, so much… Muskoka Five.

~ Sigh ~

Here we go again.

Your childhood team (and trauma) and mine, ready to sell off assets because former GM Kyle Dubas and President Brendan Shanahan wouldn’t trade Mitch Marner a few years back (and by the time Dubas apparently would, the idea in part got him fired). This was followed by current but likely not future GM Brad Treliving trying and failing to trade Marner at last year’s deadline.

Time to sell, which means selling only the obvious players (UFAs), selling players with term and value, or gutting the entire deal and going for a one-two punch of either Ivar Stenberg or Rocky McKenna this year, and Landon Dupont next year.

Oh, wait, current GM Brad Treliving destroyed that as an option with the trades for Brandon Carlo and Scott Laughton that we all know and loathe. Very well then, on with the show.

Trade #1

To Edmonton:

• Bobby McMann, LW/RW

• Scott Laughton, C/LW

To Toronto:

• Andrew Mangiapane, W

• Edmonton’s 1st Round Draft Picks in 2027 and 2029 (top-5 protected)

• Either Edmonton or St. Louis’ 3rd Round Draft Pick in 2028 (whichever is better)   

• Toronto retains 50% of each contract

Nicolas Roy is now being rumoured to go to Edmonton. I’m sticking with Laughton, as Roy has term and Toronto is not going into a full rebuild. I’ll also argue that Laughton is as good as Roy (who’s having a down year this year, thank future former Head Coach Craig Berube). I went into detail on this one last week, the only change being subbing out Henrique (who has a full NMC and may not waive, for Mangiapane, who’s as good as gone and makes more than Henrique. Suffice to say, if Toronto fails to get 1st round picks for both McMann and Laughton, it will be seen as a failure to many Leafs’ fans, myself included.

Trade #2 (I’d make a “second suitor” Mallrats joke here with a link, however it’s likely not nearly PG enough to do, so feel free to search it out on your own and laugh between crying over this team that doesn’t care about any of us enough to be worth crying over, yet we still do, because as Leafs fans we’re gluttons for punishment and truculence.)

To LA:

To Toronto:

The 31-year-old Domi has a partial no-trade clause, and two years remaining after this at $3.75M per season. Kings’ GM Ken Holland, he of the Cody Ceci and Brian Dumolin signings this summer, went all-in this year with the Artemi Panarin deal, only to have the Olympics ruin the moment with the Kevin Fiala injury. So what do you do when you’re all in and flush with around $13 million in cap space? You double down, of course.

Did I mention that Quinton Byfield is out with a mysterious upper body injury? And did I mention Ken Holland?

Domi actually would shore up LA’s 3rd line, and he showed with Dallas a few seasons ago that he can play a solid 3rd line C, at least into the Conference Finals. His defensive warts weren’t as apparent during that run, though they still showed up. Vincent Trocheck is staying in the East (or Central, ahem Minnesota). I don’t think LA can swing a deal for Robert Thomas or Ryan O’Reilly (they don’t have the assets and O’Reilly likely isn’t being dealt). If they can’t or don’t want Nazem Kadri’s contract (three years after this at $7M per, and Kadri has a 13-team no trade list this year), then who’s left? Domi is affordable, a veteran, hasn’t played yet in LA (this trade would get Domi within Mike Sillinger range for number of teams), and has likely boosted his value to a veteran GM like Holland with his recent production alongside Auston Matthews. Knowing that you could put Domi with Panarin makes it easier to talk yourself into the unique hockey player that is Max Domi

Trade #3

To Dallas:

To Toronto:

Maccelli is the textbook Dallas Stars’ trade deadline acquisition: a player with some skill who is overall an incomplete player, and will absolutely make a costly mistake or two during the playoff run, playing his role in Dallas once again not winning the Stanley Cup. The holes in his game are his ability to score and his physicality, two key traits that playoff winners have. That said, his playmaking is above average and he’s quite solid defensively, not to mention is a huge upgrade on the entire 3rd and 4th lines currently dressing for Dallas.

Flush with salary cap space now that Tyler Seguin is officially out for the rest of the regular season and playoffs, Dallas has the ability to make multiple trades. Players such as Oliver Ekman-Larsson and Brandon Carlo should also be of interest to Dallas (potentially more on them later, we’ll see), though their 4th line really needs help as I noted in the article linked in the first trade.

Once Berube started playing Maccelli, and once he left him on the left side of the ice instead of the right side (I may have written about this topic earlier in the season), Maccelli started performing up to his level. His 10-16-26 in 50 games is misleading due to not being used properly early in the season and Toronto being a mess right now. Maccelli is an RFA, which gives him value, easily enough to get their own 2026 7th round pick back (which Toronto traded at the 2024 draft to get the rights to Chris Tanev) if not more.

Trade #4

To Detroit:

To Toronto:

Lorentz was the 13th forward on Florida’s first Stanley Cup-winning team, so he brings that experience into the Red Wings’ dressing room. And while I’m sure we’re all familiar with the work of Dominik Shine (seriously, good job never giving up, very cool story), Detroit could use the depth. Lorentz has one more year on his contract at $1.3M, a very affordable number for a team $12M+ from this year’s cap ceiling.

Trade #5

To Vegas:

To Toronto:

Toronto and Vegas are recent trade partners (not going there), so it’s certainly possible for this to happen.

Here’s the Vegas surprise, having enough cap space to pull this trade off. OEL’s $3.5M cap hit this year and next year is very affordable for someone who first played their way onto Team Sweden at the Olympics, and then moved up from the 7th D slot into the rotation during the Olympic games.

Even though they’ve won their last two games, Vegas is 3-5-2 in their last 10, their goaltending is still a mess, and Rasmus Andersson has not given their D enough to stabilize things. Adding OEL gives Vegas a deep top-6, allowing them to sit Jeremy Lauzon and perhaps taking a bit of pressure off 35-year-old Brayden McNabb, who Vegas will need to play a true shutdown role in the playoffs.

It would be some serious hubris for Vegas to leave this pick unprotected, and if this was my team, that would be my push, just in case the wheels fell off the VGK wagon a couple of years from now.

You could also potentially trade RHD Troy Stecher for a 4th-7th round pick, though his play has fallen off considerably since he was first claimed on waivers, and he was benched on Monday night vs Philadelphia, so his value is likely minimal at best.

Toronto’s key asset haul from these trades:

• Edmonton’s 1st Round Draft Pick in 2027 (top-5 protected)

• Vegas’ 1st Round Draft Pick in 2028 (unprotected)

• Edmonton’s 1st Round Draft Pick in 2029 (top-5 protected)

• Dallas’ 3rd Round Pick in 2026 Entry Draft

• Either Edmonton or St. Louis’ 3rd Round Draft Pick in 2028 (whichever is better)   

Three first round draft picks with very limited protection (remember, if Edmonton got one of the top-5 picks in 2027 and/or 2029, Edmonton would keep the pick and Toronto would instead receive Edmonton’s 1st round draft pick in the next season, unprotected. There’s some upside play there, specifically with the 2029 draft pick if Connor McDavid leaves after the 2028 season.

Which brings us to the bonus section. I haven’t hit 3,000 words yet (somewhere, Dave is crying tears of joy), so let’s really open things up and get creative.

We’re going to look at two bonus trades, deals that I would consider virtually impossible, let still fun to examine. Only one of the two could happen. Which would you like more?

Better get this on the screen before Buffalo goes and does something crazy.

The Impossible Option, Part One

To St. Louis:

• Edmonton’s 1st Round Draft Pick in 2027 (top-5 protected)

• Vegas’ 1st Round Draft Pick in 2028 (unprotected)

• Edmonton’s 1st Round Draft Pick in 2029 (top-5 protected)

• Ben Danford, RD (Toronto’s 1st Round Draft Pick, 31st overall, in 2024)

• Tinus-Luc Koblar, C (Toronto’s 2nd Round Draft pick, 64th overall, in 2025)

To Toronto:

Imagine for a second, this:

Line 1: LW – Matthew Knies  C – Auston Matthews 

Line 2: LW – John Tavares  C – Robert Thomas  RW – William Nylander

The Core Four is back, baby, with a fifth to boot!

Did that sentence also make you feel, well, icky? Good, then my work here is done. Seriously though, a Matthews-Thomas one-two punch down the middle is what championships are made of. Both great offensively, both great defensively, and Thomas adds a new playmaking element to the power play. Move Tavares over to LW beside either Thomas or Matthews (if Matthews, shift Knies to RW) with far less responsibility and still rely on him for key faceoffs, give Nylander fresh blood up the middle, and you’ve got a top-5 forward group that would be the envy of most teams in the league.

St. Louis is apparently asking for three top-15 pick-level assets, and since Toronto doesn’t have that, they lottery gaslight and volume St. Louis into submission, since apparently the Blues are very open to the idea of trading Thomas. Danford, 6’2”, 200 lbs gives St. Louis their next potential shutdown RHD. He didn’t show great for Canada at this winter’s World Junior Championships, however the fact that he was chosen speaks volumes for his defensive acumen and hockey IQ. Add to that his leadership qualities (wore the “C” for 1+ seasons in Oshawa of the OHL before a trade to the Hyman family-owned Brantford Bulldogs).

Koblar is 6’3”, 198 lbs, fast, and was a high-upside play by Toronto last summer. Reports this year are that Koblar is playing well in his first year in the Swedish Elite League with Leksands, scoring at a 3rd-line rate as an 18-year-old.

Will this happen? No, but I’m sure you’ll hear on the Monday after the trade deadline how “Treliving was in on everything”, as he apparently always is. There’s a difference between being in on something, and doing something, which is part of why Toronto is in this mess. This trade does something, in that it keeps Toronto’s contender window open and gives Matthews plenty of reason to re-sign here (yes, somehow, we’re coming up on that again soon).

The Impossible Option, Part Two

To Boston:

• Any three of O E-L, Carlo, McMann, and Laughton they want, with 50% retention on both forwards.

To Toronto:

So, Don Sweeney wants to build his Bruins up. Well, Toronto is here and happy to help.

Yes, you could make this trade the same way as the St. Louis trade, however Boston is currently in the 2nd Wild Card spot in the East, 4 points up on Columbus (who only has one game in hand). Any GM worth their contract who is going to make this trade is going to take 3-4 pieces that would help their team this year (and in the case of the D, next year as well) to make a surprise run at the Cup right now. What’s that, you’d argue that any GM worth their contract isn’t making this trade in the first place? I don’t think it’s that simple. What’s worth more, Toronto’s pick, which unless they win the lottery ends up in the 5-8 range, where you’re getting a good player but no guarantee of a superstar or even a star, or the ability to take a real run at the Stanley Cup this year while shedding fat and setting yourself up better for next year as well?

A team can hold up to 50 contracts at any one time. Boston only has 44 contracts, so zero issue there.

On Toronto’s side, the potentially acquired assets from these three players is a lot of volume to give up in order to rectify a mistake. It’s likely though that we’re taking late-first round pics though, and the reality there is no one is trading a top 5-8 draft pick for a 29th and a 32nd pick, so it would take three picks/assets to make this work. Also, since this reverses the Defenseman for 1st round pick aspect, it’s not as bad as it the media would make it out to be. Yes, Minten is gone, but he’s a sunk cost, let it go. The Toronto draft pick wasn’t as valuable last year because Toronto was still projected to be a playoff team without Marner. That context really matters here. The reality however is that Toronto won’t make the playoffs, and that has raised the value of this draft pick. This allows Boston to leverage that value to make a run at the Cup, and let Toronto save some face in return. All deadline trades involving major assets are risks taken willingly by teams. Boston still likely wins this deal, which is why it’s worthwhile for them to explore this.

Boston is looking for an RHD to replace Andrew Peeke, and either/both Toronto D here would be a strong step up on any of Peeke/Henri Jokiharju/Andrew Harris

Cap implications – who else gets added to the deal?

Boston currently has just over $1.1M in available cap space, not enough to add any of these players on their own. This is why Toronto is retaining half of both forward contracts in this deal, which they can do as they currently are not using any of their retention slots. In this exercise, we’ll give Boston the trio of Laughton, McMann, and Carlo (he’s a known commodity, much easier for both him and the team to acclimate, is younger, safer defensively, and slightly less cap hit).

Boston has the leverage here, so this is a fat-cutting exercise for them. They don’t have to go for it with an 8th seed, they can make $9-15 M in gross revenue from 2-3 playoff games, lose in the first round, and keep Toronto’s pick. If they’re choosing not to, then Toronto will take the players that Boston gives them in order to secure that draft pick. As such, the trade would look like this: