This article was originally posted in March, and was reposted in May, 2020 as part of the Retro May look back at our work over the years on the anniversary of Kyle Dubas’s hiring.

There’s no way to open any kind of writing about the real world right now, not even trivial hockey blog writing, without mentioning the plague staring us all in the face. This is a one hell of a scary time, and we don’t know how bad the COVID-19 outbreak is about to get or what more demanding measures we’ll have to abide as we try to face it. We don’t know how bad the economic and social damage will be when it’s finally under control, and worst of all we don’t know who we’ll lose before that time comes.

There’s also not much going on in hockey now, obviously enough. The NHL was eminently right to suspend its season. I don’t know when it’ll be coming back, and in any case sports are about the trillionth most important thing going on right now. But that unimportance is the point of sports. They’re something to care about that doesn’t ultimately matter too much. They give us an outlet to ride the emotional highs and lows, or argue with friends, without real consequences staring us in the face. (Unless you bet the house on a Leafs Cup, in which case you’re a real sucker for lost causes.)

And many of the measures to deal with the novel coronavirus involve a whole lot of being pent up at home and not going out for fear of getting yourself or others sick. So while it ain’t much, the most useful service we can provide here is to gin up the odd article where you get to think about something else for a while and argue in the comments. Actually, not to brag or anything, but I’ve had several people tell me my articles “took forever to finish” or “wasted [either my or their] time”, so clearly this is my goddamn moment.

So!

Near the end of Lou Lamoriello’s reign as Toronto Maple Leafs GM, I did a move-by-move breakdown of his tenure. I did this again after the first year of Kyle Dubas’ tenure, on April 29th of last year. I’m doing this next installment of the series a little earlier than intended, but the idea is otherwise the same.

Excepting moves of a purely minor-league significance, I am including signings, draft picks, trades, and (spoiler alert) coaching changes. With one specific exception I have not tried to guess who else in the Leafs’ front office may have been influencing the moves; when you sit in the big chair, you own every decision.

The breakdown is as follows:

  • One-line summary: What it sounds like.
  • How significant was it? Did this make a big difference in impacting the team and its future prospects?
  • How difficult was it? Was it a gimme, or did it require some real management finesse?
  • How good was it? How has it turned out?/

I am enormously indebted to Cap Friendly for their GM records, which made this piece much, much easier to compile than it was when I did the Lou Lamoriello one. God bless you, CF. The article is still going to be super long, though.

May 1-7, 2019: Signing Korshkov, Mikheyev and Kivihalme

The Leafs sign prospect forward Egor Korshkov (two years), free agent forward Ilya Mikheyev (one year), and free agent forward Teemu Kivihalme (one year) to entry-level contracts.

One-line summary: A prospect and two nice free agent finds.

Significance: Moderate! They got a real NHLer out of it, likely.

Difficulty: The Leafs have done a good job wooing European free agents the last couple of years. They have plenty of advantages in doing that but I’m glad they do it.

Quality: Excellent, in my opinion. Ilya Mikheyev, before his season was cut short by a brutal laceration injury, immediately became a fan favourite in Toronto and was on his way to an excellent debut season. Assuming he returns at 100% whenever the season resumes or next year, he looks to be a solid Top 9 LW with an impressive motor and a likable personality. Korkshov will forever be considered something of a disappointment based on who he was drafted ahead of in 2016 (most notably Alex Debrincat), but he has some decent playmaking to go with good size. I think he’ll be a bottom-sixer in the NHL. Kivihalme probably tops out at the AHL level, but he looks neat there, and that’s okay.

May 30, 2019: Gordeev for a 7th

The Leafs trade prospect defenceman Fedor Gordeev to the Minnesota Wild for a seventh-round pick in 2020, conditional on Fedor Gordeev signing an entry-level contract with Minnesota. He did.

Significance: What’s the smallest number that’s still bigger than zero?

Difficulty: Good on Dubas for hunting down a taker for a player whose rights were about to expire. The Leafs weren’t going to sign him, so any return is a plus.

Quality:

June 22, 2019: The Marleau Sale

The Leafs trade veteran forward Patrick Marleau, a conditional 2020 first-round pick, and a 2020 seventh-round pick to the Carolina Hurricanes for a 2020 sixth-round pick. If the Leafs’ first falls in the top ten in 2020, the pick will turn into an unprotected 2021 first. Subsequent to this trade, the Hurricanes immediately buy out Marleau’s contract.

One-line summary: A high but necessary price.

Signficance: The Leafs cleared $6.25M against their salary cap, money which they sorely needed considering they wound up capped out almost to the pennies. Marleau’s cap hit would almost definitely have cost the team at least one of Andreas Johnsson and Kasperi Kapanen, would have required a bridge on the other, and would have made the Mitch Marner negotiation even more of a nightmare than it became. It was important.

Difficulty: It’s worth a brief reminder what the circumstances were here. Patrick Marleau had a no-move clause and he, apparently, only wanted to play for the San Jose Sharks. The Sharks couldn’t have afforded to acquire him at his big $6.25M cap hit even if they’d wanted to, because they spent all their money building a team that immediately went out and flopped like a dying fish. Anyway: Marleau was only waiving for a team that would buy him out so he could then go sign in SJ. That meant he had to be waived to a team that could buy him out, including paying his signing bonuses, and could also stand his whole cap hit—which, as an over-35 buyout, would sit as a full $6.25M on their cap sheet, unless the Leafs retained salary, which obviously would have limited the benefit. The buy-out window would have expired in a week, and then this whole maneuver would become impossible. Short version: the Leafs were really up against it here.

Quality: Look, it’s a painful price. I don’t doubt Dubas surveyed the market as best he could and took what was available. Unlike most trades that involve players, this one didn’t really change the value of the return based on buyer. The price was Toronto's first for $6.25M in cap space. Yes, it’s not fun to give assets to fix old mistakes and it doesn’t look as good next to the David Backes/Ondrej Kase trade. But Kyle Dubas was boxed into a corner not of his own making and I think he did what he had to do to get out of it. Also, that top-ten protection on the pick was a good move.

June 21-22, 2019: The 2019 NHL Entry Draft

The Leafs draft forward Nicholas Robertson (53rd overall), defender Mikko Kokkonen (84th overall), forward Mikhail Abramov (115th overall), forward Nick Abruzzese (124th overall), defender Mike Koster (146th overall), and defender Kalle Loponen (204th overall.)

One-line summary: Gold, baby!

Significance: Drafting is important for keeping a pipeline of contract-controlled talent into your franchise. Also it gives blogs things to talk about in the summer.

Difficulty: It’s hard to draft well! Harder still when you have zero picks in the top fifty. (To be clear, the trade that cost us this first was the Jake Muzzin deal, not the Marleau trade.)

Quality: If you aren’t excited about Nick Robertson, who dominated the OHL in goal-scoring this year, you’re down with anhedonia or something. He looks like he should have been a late first-rounder at the least. Getting him at 53rd overall is terrific. As for the rest of the longshots in this draft, Mikhail Abramov has been clobbering the QMJHL and Nick Abruzzese had a good enough college year to be worth mentioning. We won’t truly know the outcome of this draft for five or six years, but one year out it looks stupendous.

(Oh, and Dubas signed Robertson and Abramov to ELCs in September and March, I figured that didn’t need another section.)

June 27-29, 2019: Signing Hutchinson, Kapanen, Johnsson, and Marincin

The Leafs sign goaltender Michael Hutchinson for one year at $700,000 AAV, forward Kasperi Kapanen for three years at $3,200,000 AAV, forward Andreas Johnsson for four years at $3,400,000 AAV, and defender Martin Marincin for one year at $700,000.

One-line summary: Not much special value, but mostly decent signings.

Significance: Two key forwards (good significance), one disastrous backup (bad significance), and one seventh defenceman (life-changing significance.) We will talk more about Hutchinson when we get to the Jack Campbell trade, so I’ll save that discussion for then.

Difficulty: I doubt anyone was bidding super hard against us on Marincin/Hutchinson, honestly.  Kapanen and Johnsson could conceivably have attracted offer sheets had this gone into July; they’re very rare, but they would have made a lot of sense. So who knows?

Quality: Johnsson and Kapanen are two solid second-line wingers, although Kapanen always seems to do best as a 3RW. I wouldn’t say either deal is solid gold, but neither is bad; if you traded either of them you’d certainly get an asset back. Michael Hutchinson tragically was abducted by aliens before he could play any games on his contract. Martin Marincin did exactly what he was paid to do, so eat it, haters.

July 1, 2019: The Zaitsev Trade

The Leafs trade winger Connor Brown, defenceman Nikita Zaitsev, and prospect Michael Carcone to the Ottawa Senators for defenceman Cody Ceci, defenceman Ben Harpur, and forward Aaron Luchuk. The Leafs clear $5.875M in cap space for 2019-20 on the transaction, later reduced to $1.375M once Ceci is signed (more on that later.)

One-line summary: We’re free of the Zaitsev contract!

Significance: Lou Lamoriello signed two really bad deals in the course of his time running the Leafs. One was the Patrick Marleau deal, and the other was the Nikita Zaitsev extension, which had a whopping five years left on it at this point. Dubas disposed of one and then the other in the course of ten days, clearing considerable cap space, and got back only unsigned RFA Cody Ceci and some spare parts.

Difficulty: It’s always good to find those teams that want players with bigger cap hits than salaries. Since Brown ($500,000) and Zaitsev ($3,000,000) both had signing bonuses that were payable on July 1, 2019, the Leafs were able to keep some of the actual dollar amount while dealing the full cap hit to the cash-strapped Senators. Even granted Ottawa loves those contracts, I was impressed Dubas unloaded the Zaitsev contract without paying a punitive cost to do so. That wasn’t a given.

Quality: Carcone and Luchuk don’t really matter for NHL purposes, and thankfully the Leafs had the sense to leave Ben Harpur in the AHL (also, the Leafs traded away Luchuk and Harpur for different AHL players last month.) So it comes down to giving up Connor Brown to get rid of Zaitsev’s contract, with Ceci as a depth guy and contract makeweight. Connor Brown isn’t a bad winger, but he was down the depth chart for Toronto—yes, he’s since had a very productive year for the Sens, but that’s partly because he gets more ice-time than any other forward on the team, and $2.1M was simply too much money for where he likely would have been used. I think this deal looks very solid.

July 1st, 2019: The Kadri/Kerfoot/Barrie Trade

The Leafs trade centre Nazem Kadri, defenceman Calle Rosen, and a 2020 third-round pick to the Colorado Avalanche for defenceman Tyson Barrie (50% salary retained), forward Alexander Kerfoot, and a 2020 sixth-round pick.

One-line summary: Well, it was worth a try!

Significance: Kyle Dubas had one major asset that seemed primed for trade in Nazem Kadri, and he used it here to get his 3C of the future and his 1RD of the next year—or so it was hoped. This remains the biggest trade of his tenure so far, at least in terms of names involved.

Difficulty: Well, for one, Kadri employed his limited no-trade clause to block a previous trade to the Calgary Flames, so it’s not like Dubas had the whole league to deal with on this. Second, Dubas had to simultaneously try to upgrade at 1RD, find a replacement at 3C, and stay within the salary cap. In light of those intermingled goals, it’s understandable that the solution wasn’t perfect, and it’s arguably impressive that he managed as well as he did. This trade was one of the defining ones of the year for Toronto.

Quality: Hoo boy. To start off with, the Leafs likely knew they were giving up the best player in the deal here, and that certainly seems true in hindsight. Kadri remains a quality 2C on a good deal for a couple of years to come. Alexander Kerfoot has had a good year for the most part, even if current coach Sheldon Keefe is a bit ambivalent about playing him at 3C and not 2LW. Tyson Barrie, in my opinion, has been a disappointment. He looks to me like an excessively shot-happy 4/5 defenceman who puts up points without contributing real value commensurate to the totals he gets. He’s not unplayable or anything, but I expected more, and I certainly don’t want to be the franchise signing his next deal. The loss of pick value from a third to a sixth is not all that big a deal and we actually got Calle Rosen back later, so that’s about the size of it. I think I am still narrowly all right with this deal, because I like Kerfoot, but we didn’t improve as much as I would have hoped we would have in giving up a very good player.

July 1st, 2019: Leafs Sign Spezza, Shore, Agostino and Gravel

The Leafs sign sign forward Jason Spezza (one year at $700,000), Nick Shore (one year at $750,000), Kenny Agostino (two years at $737,500 AAV), and Kevin Gravel (one year at $700,000.)

One-line summary: Boy, Kyle had a busy Canada Day, eh?

Significance: Spezza has been a very solid depth contributor for the Leafs all year, on and off the ice. The rest didn’t matter too much to NHL fans.

Difficulty: I doubt Kyle strained any muscles on these.

Quality: Spezza is an excellent addition. I liked the Nick Shore pickup, and while he was very uneventful in his 21 Leaf games, he showed enough that the Winnipeg Jets claimed him on waivers and they’ve been playing him a bunch. Agostino has been a great AHL player and might still pop up in the NHL in the second year of that deal, Gravel is depth. Not bad.

July 4, 2019: Leafs Sign Kerfoot and Ceci

The Leafs sign restricted free agents Alexander Kerfoot (four years at $3,400,000 AAV) and Cody Ceci (one year at $4,500,000.)

One-line summary: It’s mostly fine.

Significance: I think the Kerfoot deal is good and I like it, despite his middling production this season. The Ceci deal did constrain us cap wise, so let’s briefly mention why.

Difficulty: Cody Ceci had been extended a qualifying offer of $4.3M by the Ottawa Senators. A qualifying offer is the amount necessary to keep a player’s rights, and the Sens were caught by the fact that they’d previously signed Ceci to a very bad contract; the QO was determined by that previous deal and so the offer was a lot. The offer remained open at the time Ceci was traded to Toronto and wouldn’t have expired until after this extension was taken. Ceci was free to take it at any time, with no further action by the Leafs, and the QO would have become a one-year deal at $4.3M.

Ceci could have elected arbitration, but there was an excellent chance that if he did so and got a meaningful raise the amount would have been one that the Leafs could walk away from, thereby letting them wash their hands of his deal altogether. So in his pursuit of a little extra money, he might have accidentally thrown away $4.3M, a salary I’d be surprised if he ever makes again because his stock has fallen around the NHL. Assuming Ceci and his agent were behaving rationally, he should have made certain to get the $4.3M, no matter what. Even if the Leafs threatened to press box him and demote him and say mean things to him on instant messenger, he ought to have made certain to get that bag.

Now, did the Leafs have to offer the extra $200,000 to give Ceci $4.5M a year? No.

Quality: It looks like the Leafs made a goodwill offer because they wanted Ceci to be happy and also because they intended to play him as a 4/5 defender. The Leafs were capped enough that $200,000 could have really mattered, but a series of injuries that helped the team stay cap compliant throughout the whole season up to the recent suspension of play meant they were never quite that desperate for the extra cap. So it looks to me like a mistake, but a minor one in terms of its impact.

Oh, yeah, and the Kerfoot deal was good.

July 23, 2019: Leafs Trade For Clarkson

The Leafs trade backup goaltender Garret Sparks for unofficially retired forward David Clarkson.

One-line summary: Be honest, this trade confused the hell out of you when it happened.

Significance: It confused everyone, including me. It was expected Garret Sparks’ time in Toronto was done, given his season ended pretty disastrously. But no one foresaw David Clarkson coming back. The short version of why the Leafs did it is that because they were already going to be using LTIR at the start of the season—with Nathan Horton, whom they originally acquired for this very same David Clarkson—it was beneficial for them to be as close to the cap as possible before using it. It would not have benefited them to acquire any more permanent LTIR contracts and it would not benefit them to get any such contracts for next season, when they shouldn’t have any permanent LTIR deals at all.

Difficulty: Leafs’ assistant GM Brandon Pridham is a goddamn wizard.

Quality: Dandy. It’s nice to have smart people run your team.

July 24, 2019: Leafs Sign Pontus Aberg And Some Other Guys

The Leafs signed another bunch of players but the only one of them that has much NHL significance so far is Pontus Aberg (one year at $700,000.)

One-line summary: Sure, cool!

Significance: Exceedingly modest!

Difficulty: Exceedingly low!

Quality: Pontus Aberg looks like an odd tweener player who doesn’t quite play a complete enough game for NHL coaches, but who produces reasonably there and very well in the AHL. I’m certainly happy taking a shot on those guys even if it’s mostly an AHL signing.

September 13, 2019: The Mitch Marner Extension

The Leafs sign winger Mitchell Marner to a six-year deal at $10,893,000 AAV.

One-line summary: He’s a very good player and it’s just too much money.

Significance: Mitch Marner is an outstanding young winger and a core player on this team. He was the last of the Big Three young players the Leafs sought to sign, one of their Crown Jewels, the last “we can” to turn into a “we will.” He puts up points like nobody’s business, and without him this team is much, much worse. He also signed for the third-highest RFA AAV in history, behind Connor McDavid and Auston Matthews.

Difficulty: It sounds like this negotiation was a nightmare. Darren Ferris played hardball commented through the media, and generally—sorry—did a hell of a good job for his client. It did burn some goodwill with this fanbase, perhaps, but Mitch did extremely well out of it and still has endorsement deals with seemingly every business in Toronto. Whether you resent him negotiating hard for every dollar is your call (I don’t), but it seems to have worked. Anyway, Marner apparently did solicit offer sheets and was in talks with Columbus for one, but they couldn’t agree on term and Marner did want to stay in Toronto. Just not enough that it saved us much money.

Quality: I really want to hammer two points here: Mitch Marner is a really great player, and his contract is an overpay. People, on both ends of this argument, tend to argue against one point to prove the other, and that doesn’t work since they’re both true. He’s one of the most gifted playmakers in the NHL, and players with assist rates like his at his age have a way of winding up in the Hall of Fame. Is he worth an extra $1.64M a year more than Mikko Rantanen, who signed two weeks later for the same number of years? No. Is he worth so much more than Brayden Point (three years at $6.875M) or Matthew Tkachuk (three years at $7M) that the extra three years of term make up for the ~$4M extra a year in AAV? No. And as good as Marner may yet become, all of those contracts were signed in September 2019. The Leafs had the biggest overpay of the bunch.

This certainly could have ended up worse for Toronto. Maybe Marner would actually have signed an offer sheet, and that might well have wound up costing the Leafs even more money, or worse, losing them the player. I’m glad we avoided those outcomes. But Marner won this negotiation, and the Leafs lost it.

November 20, 2019: Leafs Fire Mike Babcock, Hire Sheldon Keefe

The Leafs dismiss head coach Mike Babcock and replace him with Sheldon Keefe, who is immediately signed to a three-year contract.

One-line summary: Kyle Dubas gets his man in charge.

Significance: Pretty huge. Dubas dismissed the highest-paid coach in the NHL with three and a half years left on his deal, a coach who still had a very impressive resume, and hired his own chosen candidate without any further searching. This might be his biggest move of the year. Oh, and Babcock’s firing led to revelations about his coaching style and that of others throughout hockey, in a chain reaction that engulfed the hockey world for a time.

Difficulty: I think this might actually have been impossible, at one point. It is not clear whether or not Kyle Dubas had full authority to fire Mike Babcock last spring, when it was discussed internally. It’s possible that Brendan Shanahan wouldn’t allow it, and only the team’s early struggles in October and November changed Shanahan’s mind. It’s also possible Dubas simply didn’t reach the point where he was comfortable making such an enormous move.

Quality: I think it was past time to fire Babcock, as it turns out, and that seems to have been the consensus. Whether you judge Dubas for not doing it sooner depends on whether you think he could have. The early returns on Sheldon Keefe as Leafs’ head coach have been positive, but there are still plenty of bumps in the road and much remains to be written. I would call this a good move from where I’m sitting today.

December 31, 2019: The Justin Holl Extension

The Leafs sign defenceman Justin Holl for three years at $2M AAV.

One-line summary: A decent 4/5 RD, of which the Leafs have several, but Holl might be the most reasonably paid.

Significance: I wouldn’t say he’s a core piece or anything, but Holl has been leaned on pretty heavily this season and has, in my opinion, been good enough to be useful. He and Jake Muzzin might be called upon to be a no-doubt-about-it second pair next season. That’s big.

Difficulty: Not a ton, I’m assuming.

Quality: Holl’s deal seems reasonable to me for what we rely on him to do, and it doesn’t seem out of proportion to comparables like the Greg Pateryn or Nick Jensen contracts. Holl had a limited NHL track record, but so far it’s good enough that I like this deal.

January 10, 2020: Leafs Extend Martin Marincin

The Leafs sign franchise defenceman and star of my heart Martin “Marmar” “Marv” “The Gangster” Marincin to a million-year extension at a trillion dollars per.

One-line summary: Fine, it was one year at $700,000, whatever.

Significance: Infinite.

Difficulty: Heroic.

Quality: Unimpeachable.

February 5, 2020: The Moore/Campbell Trade

The Leafs trade forward Trevor Moore, a third-round pick in 2020, and a conditional third-round pick in 2021 to the Los Angeles Kings in exchange for goalie Jack Campbell and forward Kyle Clifford (50% retained.) The condition on 2021 the third is that it becomes a second if one of two conditions are met: Kyle Clifford signs an extension with Toronto OR Jack Campbell wins six or more games while the Leafs make the 2019-20 playoffs. At the time the season was suspended, Clifford had yet to sign and Campbell had won three games. What might become of this condition if the season is canceled before the playoffs, I do not know, though I think the Leafs would have a strong argument it was not met.

One-line summary: The Leafs finally get a backup goalie.

Significance: So, you likely remember this, but throughout the season, the Leafs were struggling mightily with backup goaltending from Michael Hutchinson that just wasn’t adequate (and their starting goaltending was hit and miss, too.) Jack Campbell has been much better than Hutchinson in limited work for the Leafs, while Kyle Clifford has been the fourth-line energy player he’s been advertised to be.

Difficulty: Good question! Was the market so unforgiving and impossible that Dubas couldn’t make this deal earlier? Did he just not want to until he had no choice (the price in picks was probably a little steep for the value, unless Campbell keeps blazing and turns into a starter)? It’s hard to say. Dubas knew Campbell from the OHL, so it’s quite possible he had his eye on Jack for some time.

Quality: It’s a bit expensive, but the early returns looked good. The question was why it took so long. Hutchinson did have a miniature resurgence under Sheldon Keefe before falling back again, but the Leafs left a lot of points on the table through bad backup goaltending. If you’re going to criticize this move, I think my criticism might be more that it became necessary: the Leafs didn’t have any response when Michal Neuvirth proved too injured to play after a pre-season try-out and Hutchinson fell apart. They were left floundering for a period and lost points doing so. That’s not great.

February 12, 2020: The Engvall Extension

The Leafs sign forward Pierre Engvall for two years at $1.25M per.

One-line summary: I, for one, welcome our new giraffe overlord.

Significance: Engvall has been one of the more pleasant Leaf surprises this year. A recent point slump notwithstanding, he looks like he’s an NHL player with a knack for penalty killing, good speed, and a long reach. Locking up such players is a good idea, as the Leafs continue to surround their stars with value contracts.

Difficulty: Nil, I figure.

Quality: I’m pleased with it. Engvall is older than you might think (he’ll be 24 in May) so I don’t know that there’s a ton of growth left there, but I’m willing to accept the slight risk of having to bury $300K for the chance of having a 3LW on a quite reasonable contract.

February 19, 2020: Marchment for Malgin

The Leafs trade forward Mason Marchment to the Florida Panthers for forward Denis Malgin.

One-line summary: A fringe NHLer for an AHLer.

Significance: Not enormous, although Malgin has played as high up as the second line at times in Toronto.

Difficulty: I mean I hate to say it, but taking a player in a PDO slump from a team run by Dale Tallon is a bit like taking candy from a baby.

Quality: Some people responded to this one with an eye roll for yet another small forward, but I think this is a fine piece of work. Marchment is a nice kid and big, but he doesn’t look like an NHLer to me and in June he’ll be 25. I don’t think it’s likely to happen. Malgin looks like he can at least contribute in the NHL, notwithstanding his lack of points in blue and white thus far, and he just turned 23. Even if Malgin just turns out to be Seth Griffith 2.0, this is the kind of trade I’m happy making.

February 24, 2020: Hutchinson for Rosen

The Leafs trade goalie Michael Hutchinson for defenceman Calle Rosen.

One-line summary: To be honest the above line is about it.

Significance: Very minor.

Difficulty: Rosen wanted to come home, Hutchinson was done in Toronto. Natural fit.

Quality: Rosen is a fringe-y NHL defenceman, but that’s something and Hutchinson was more or less finished as an NHL goalie. This is very debatably an NHL deal, but Rosen has played for Toronto since being acquired, thanks to injuries, so it counts. He’s a credible enough 7D who can skate.

February 24, 2029: The Leafs Buy A Draft Pick

This is a three-way trade, but the Leafs were a facilitator in a deal that was really happening between the Chicago Blackhawks and the Vegas Golden Knights. So from that perspective:

The Chicago Blackhawks trade goalie Robin Lehner (retaining 50% of his cap hit, or $2.5M out of his $5M AAV) and prospect forward Martins Dzierkals to the Vegas Golden Knights. In exchange, the Hawks get goalie Malcolm Subban, defence prospect Slava Demin, and a 2020 second-round pick.

On his trip from Chicago to Vegas, Robin Lehner stops off in Toronto long enough for the Leafs to retain 44% of his remaining salary—keep in mind this is after the Blackhawks already retained half of it, so the actual impact is Toronto retaining a $1.1M cap hit for the rest of this season, while Vegas winds up with $1.4M on a contract that originally had an AAV of $5M. For their assistance in eating some of this salary, the Leafs get a fifth-round pick.

One-line summary: They bought a fifth-rounder.

Significance: Not huge. Fifths are what they are. But you’d rather get them then not.

Difficulty: Once MLSE was willing to spend the money, not a ton. I like that the Leafs are keeping open to these transactions and taking action when the opportunity strikes.

Quality: Es bueno.

February 24, 2020: The Jake Muzzin Extension

The Leafs sign defenceman Jake Muzzin to a four-year extension at $5.625M AAV, kicking in next year.

One-line summary: The Leafs lock up their best defensive defenceman, even though he just turned 31.

Significance: If the Leafs hadn’t kept Muzzin, they would likely be trying out Rasmus Sandin as their 2LD next year, or else shopping in what is shaping up to be a wildly unpredictable free agent market with some iffy defencemen. Or they’d be making a trade. So he’s a key piece; at the same time, they’ve tied up a lot of cap in Muzzin’s declining years.

Difficulty: Muzzin seems like he wanted to stay. It is worth noting the Leafs, as is their habit, loaded the deal with signing bonuses. They also had the no-movement clause drop to a no-trade in year two, and then a modified no-trade in year four. This means the Leafs don’t have to shield Muzzin in the expansion draft with Seattle if they don’t want to, and should they decide to trade Muzzin for the fourth year of his contract, his real salary will be much diminished—something you may recall made the Nikita Zaitsev deal more appealing to Ottawa in a trade.

Quality: I’ve been on the fence about this one, but in the end, I like it. It does have downside risk, and when age comes for players after 30—especially players with a physical style, like Muzzin—it can come very quickly. Still, he remains a very solid second-pair defenceman, and if he can keep providing that value for at least the next two seasons and still be respectable in Year 3, this deal is probably enough of a win. Our team is trying to win now, and replacing Muzzin would have been extremely uncertain.

Conclusions

  • Let’s start with the best part: Dubas’ drafts, at this early date, look excellent. Rasmus Sandin and Nick Robertson already seem like clear steals for their draft spots, and there are interesting players up and down the board.
  • Nothing that Dubas has done has seemed indefensible to me. When Dave Nonis signed the David Clarkson contract, it was a disaster on Day 1 that only got worse. Dubas has made no trade or signing that I thought was deeply flawed in its conception.
  • The Ceci-Zaitsev trade looks like a clear win for the Leafs to me, and the Kadri trade is painful but respectable, as is the price we paid to deal Marleau.
  • Dubas probably did not capture exceptional value on his RFA deals with Kerfoot, Johnsson, Kapanen, and (lol) Ceci. I also don’t think he wasted any inordinate amount of money, and you can argue he shielded Johnsson and Kapanen from any potential offer sheets, insofar as those are a concern. The Ceci deal looks like a waste of $200K. More’s the pity.
  • He overpaid Mitch Marner. If you want more on that, I reacted here at the time.
  • He arguably waited too long, or at least did not come up with a sufficient alternative, on the backup goaltending. I go back and forth on how much blame that’s worth assigning, and I think reasonable people can argue there. His eventual trade to resolve it has had good early returns.
  • His coaching change looks pretty good so far.
  • Dubas continues to do lesser moves well, such as picking up Ilya Mikheyev and Jason Spezza or grabbing a fifth-rounder to facilitate the Lehner deal. This may seem like damning with faint praise, but for a team that has much of its core in place, finding value wherever you can is important. One of the things that encourages me most about Dubas is those small deals.
  • The Leafs under Dubas continue to operate like a smart front office. They make creative deals like the Sparks/Clarkson one and the Lehner deal; they don’t wade foolishly into unrestricted free agency (and for the record, I will stand by the Tavares signing forever.)
  • In the end, if there’s a knock on Dubas, it’s that this mix of defensible missteps and clever upgrades has not netted out to a real, substantial improvement. The Leafs have not yet managed to become the top-tier team that we’d want them to become. It is possible as they mature and get more used to Sheldon Keefe that internal growth will take them the rest of the way. It is possible Dubas will pull a rabbit out of a hat to upgrade the roster, or that his good drafting will finally put them over the top. It’s possible it won’t and that in a few years Dubas’ tenure ends without significant playoff success.
  • But as it stands, right now, he’s the person I want doing the job./