The rumour, as reported by Chris Johnston on CBC during the March 3rd outdoor game, is that Lou Lamoriello will not be the General Manager of the Toronto Maple Leafs next season. He might be pushed upstairs into an advisory role. He might surprise us all and stay on.

But as the trade deadline has now passed, it’s possible the Tomas Plekanec trade was the last major move Lou made in his tenure running Toronto. In that time he’s seen the Leafs rise from dead last to a playoff team to a fringe Cup contender. How much of that is Lou’s doing? How should we evaluate his time running the franchise?

We’re going to look at every significant trade, signing, and draft, and rate them on three categories:

How significant was it? Did this make a big difference in impacting the team and its future prospects?

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?

Was it a gimme, or did it require some real management finesse? How good was it? How has it turned out?

Some preliminary notes:

Lou Lamoriello was hired on July 23, 2015, not long after the Leafs made a big trade unloading Phil Kessel. It’s worth noting that the rest of the modern Leaf braintrust—President Brendan Shanahan, coach Mike Babcock, assistant GMs Mark Hunter and Kyle Dubas, and Assistant to the GM* Brandon Pridham—was already there waiting for him when he arrived. How much of any given decision was impacted by these other five men is very difficult to say, since we weren’t in the room for any of the Leafs’ discussions. As the Leafs’ GM, I have assumed Lou Lamoriello is ultimately responsible for every decision, since he ought to have final authority on these decisions.

(*Yes, this is his actual title, I’m not making an Office joke.)

In the interests of brevity (lol), I have not included deals that seemed to have exclusively AHL significance, such as trading Viktor Loov or extending Colin Greening. Beyond that, everything is here, as far as I can manage.

Finally: this is meant to cover every NHL transaction, and also I wrote it, so it’s very long. If you’d rather just get to the conclusions, scroll all the way down and I’ll tell you what I took away from this.

September 17, 2015: The Michael Grabner Trade

The Leafs trade F Carter Verhaeghe, F Taylor Beck, D Tom Nilsson, D Matt Finn, and G Christopher Gibson to the New York Islanders for F Michael Grabner.

One-line summary: Leafs get contract slots and a winger.

Significance: Not a ton, but the Leafs did clear a bunch of SPC slots and acquire a quite useful player. The Leafs were tanking this season and Grabner walked in the summer, so they didn’t have too much enduring benefit from winning the trade.

Difficulty: The stakes were pretty low, but it was a creative little deal. Five-for-ones aren’t all that common.

Quality: Good. The Leafs got a quite good winger for five low-end prospects, and cleared SPC space. Beck, Nilsson, and Finn are in the KHL, SHL and ECHL respectively; Gibson is a third-string goalie at best and would be fifth or sixth with the Leafs. Carter Verhaeghe is the only one of the five with any NHL hopes left, and even then, he’s a pretty good AHLer at 22 right now with the Syracuse Crunch. It’s hard to object to any trade where we gave up so little and got any kind of benefit.

October 6, 2015: The Frank Corrado Waiver Claim

The Leafs claim D Frank Corrado on waivers from the Vancouver Canucks.

One-line summary: Here. This is where it began: the saga of Frank Corrado.

Significance: In reality, very little. On Leaf Twitter, somewhere between the Industrial and French Revolutions.

Difficulty: Zero.

Quality: Why not? I think CF% overrates third-pair defencemen, but I don’t mind taking a flier on them in a down year. Surely no one will get carried away with this player, right?

January 3, 2016: The Richard Panik Trade

The Leafs trade F Richard Panik to the Chicago Blackhawks for F Jeremy Morin.

One-line summary: Something for nothing, but not a lot of either.

Significance: Not much.

Difficulty: Not much.

Quality: Not great. Panik was scuffling but had something of an NHL track record already. Since the deal, Panik has played 167 NHL games, and had a surprising 22G-22A-44P season with the Blackhawks in 2016-17. He got a big raise off that year (from $875K to $2.8M), came back to Earth this year, and wound up traded to Arizona. He’s a playable NHLer of some variety, but I’d bet that 44-point year is going to be his career high, and at 27, he is what he is by now.

At the same time, Jeremy Morin played 0 NHL games after we got him and is now in the Swiss League. So we gave up a minor NHL winger for a non-NHL winger. Can’t quite spin that as a win.

February 9, 2016: The Dion Phaneuf Trade

The Leafs trade D Dion Phaneuf, F Matt Frattin, F Casey Bailey, F Ryan Rupert, and D Cody Donaghey to the Ottawa Senators for D Jared Cowen, F Colin Greening, F Milan Michalek, F Tobias Lindberg, and a 2017 2nd-round pick.

One-line summary: Leafs pay in the short term to save huge cap space in the long term.

Signifcance: Huuuuuuge. This was one of the foundational deals of the rebuild, and we would be greatly lamenting Dion Phaneuf’s contract—which would still have three years on it at $7M AAV—going into next year if Lou hadn’t made it.

Difficulty: It was facilitated by Ottawa’s desperation to save some short-term money, so part of the thanks goes to the Sens organization. But Lou moved a contract I would have thought was untradeable except for another bad term contract. Instead, the Leafs are out of the Dion Phaneuf deal with no negative cap consequences, while the Phaneuf deal itself expires in 2021.

Quality: In case you haven’t guessed, this was one of the best trades the Leafs have made this century. Dion Phaneuf had a cap hit of $7M until the end of the 2020-21 season, when his play was at the level of maybe a second-pair defenceman. The Leafs took on some short-term bad deals (Greening, Michalek) and unloaded a bunch of non-NHL players to have their worst cap albatross off the books. Yes, this was undoing an error of the old regime—tearing down rather than building up—but it’s an incredible one.

February 21, 2016: The Shawn Matthias Trade

The Leafs train F Shawn Matthias to the Colorado Avalanche for F Colin Smith and a 2016 4th-round pick.

One-line summary: Trade deadline sale.

Significance: Meh.

Difficulty: Meh.

Quality: Sure, works for me!

February 22, 2016: The Roman Polak Trade

The Leafs trade D Roman Polak and F Nick Spaling for F Raffi Torres, a 2017 2nd, and a 2018 2nd.

One-line summary: The Sharks loaded up on depth and way overpaid for it.

Significance: Moderate!

Difficulty: How the hell did he pull this off?

Quality: HE GOT TWO 2NDS FOR ROMAN POLAK AND NICK SPALING.

February 27, 2016: The James Reimer Trade

The Leafs trade G James Reimer and F Jeremy Morin for G Alex Stalock, F Ben Smith, and a conditional 4th-round pick (the condition was that the Sharks make the 2016 Cup Final; they did, so this pick upgraded to a 3rd.)

One-line summary: The Leafs gave the Sharks a goalie rental for a pick.

Significance: Modest.

Difficulty: Probably not that hard, tbh.

Quailty: This is a fine return. A lot of people felt it wasn’t because of what James Reimer meant to this team, and I understand that. But James Reimer was a goalie rental. Goalie rentals tend to go for about a 3rd-round pick. I argued this pretty exhaustively here. Given that it was the same two teams trading within the same week, you might also feel justified in linking this with the robbery return for Polak and Spaling.

February 28, 2016: The Winnik-Carrick Trade

The Leafs trade F Daniel Winnik and a 2016 5th for Connor Carrick, Brooks Laich, and a 2016 2nd.

One-line summary: The Leafs offered the Caps some cheap depth and took away Laich’s bad contract in exchange for a prospect and a 2nd.

Significance: Reasonably big for a deadline sale.

Difficulty: Not huge, but it did involve a nice leveraging of cap space—a theme in many of Lamoriello’s deals for the Leafs. It’s a lot easier to do in Toronto, who have money to burn, but some other teams with money haven’t used it with as clear an eye on the rebuild.

Quality: Excellent. Carrick is currently the second-best RHD in the Leafs organization, even if that isn’t saying a ton, and a 2nd for a depth rental is pretty nice too. You can wish they’d sold the last couple of wingers—P.A. Parenteau and Michael Grabner—but I think Lou did a pretty excellent sales job for futures and got a nice return doing so.

April 13, 2016: The Nazem Kadri and Morgan Rielly Extensions

The Leafs extend RFA C Nazem Kadri and RFA D Morgan Rielly for six years each. Kadri’s AAV is $4.5M and Rielly’s is $5M.

Significance: Foundational. There are six current Leafs who can, I think, be called core players, and Kadri and Rielly are two of them.

Difficulty: Extending RFAs is by and large, not that hard; teams have all the leverage, as nobody does offer sheets anymore. Kadri was also coming off a year where his shooting percentage was in the sewer, which likely helped.

Quality: Phenomenal. I honestly cannot believe how favourable the Nazem Kadri contract is. Rielly’s is closer to in line with his value, but still quite good for the calibre of player. This may have been easier, but the Leafs are going to benefit for years from Lou nailing these extensions.

May 2, 2016: The Nikita Zaitsev ELC

The Leafs sign RD Nikita Zaitsev away from CSKA Moscow to a one-year ELC. For the record, the length of the ELC is determined by Zaitsev’s age and the CBA, it’s not a choice thing.

One-line summary: The Leafs work the European FA market to land one of the best KHL defencemen.

Significance: Considerable.

Difficulty: The Leafs have clearly been putting a lot of work in to scout and pursue European free agents in recent years, a luxury of being a richer team. In a recent interview, Kirill Kaprizov mentioned that Russian players had noticed the work Toronto put in to woo Zaitsev, and I think the Lamoriello front office deserves a lot of credit for this.

Quality: Outstanding. Whatever you think of his extension, which we’ll get to, getting Zaitsev on an ELC was a coup. He’s the best RD in the organization right now, warts and all.

June 16, 2016: The Jared Cowen Buyout

The Leafs bought out Jared Cowen, earning themselves a cap credit in 2016-17 and a mild cap hit the year after that. Cowen contested the buyout. Cowen lost. Do not challenge Lou.

June 20th, 2016*: The Frederik Andersen Trade and Extension

The Leafs trade a 2016 1st and a 2017 2nd for G Frederik Andersen. In a separate transaction on July 8th, the Leafs send Jonathan Bernier to Anaheim for a conditional pick. The Leafs then sign Andersen for five years at $5M AAV. The conditional on the pick was never triggered and no pick was ever moved.

Normally I think it’s bad evaluation to link two trades and a signing like this, but the Leafs traded Bernier for essentially nothing: the conditional pick would have basically required Bernier to become the Ducks’ starter and take them to the Cup Final. But the Bernier trade happened after Bernier’s signing bonus was paid July 1st. This was, in effect, a way to retain real salary without using a retention slot. The Leafs extended Andersen on arrival, so we might as well take this all in one go.

One-line summary: They pay full price, but the Leafs get their starting goalie for the rest of the decade.

Significance: Huge.

Difficulty: More creative work here with the signing bonuses.

Quality: It looks fantastic now. Of all Lou’s work, I think this was the move I was really wrong about; I thought it had potential to work out well but was too big a gamble. Now it looks brilliant. Worth noting here that the 1st was the one we acquired in the Phil Kessel trade and, since the Pens had won the Cup, it was known to be 30th overall at the time of the deal, so it’s a different proposition than selling a 1st well in advance.

June 24-25, 2016: 2016 NHL Entry Draft

The Leafs drafted: Auston Matthews (1 OA), Yegor Korshkov (31 OA), Carl Grundstrom (57 OA), Joseph Woll (62 OA), Jordan Greenway (72 OA), Adam Brooks (92 OA), Keaton Middleton (101 OA), Vladimir Bobylev (122 OA), Jack Walker (152 OA), Nicolas Mattinen (179 OA), Nikolai Chebykin (182 OA.)

Significance: This draft was pretty easily the most significant thing to happen to the Leafs in this century.

Difficulty: Drafting Auston Matthews first overall was likely the easiest decision of Lou’s career. Anyone can do that. After that, it’s a lot harder. Drafting is no joke.

Quality: Again, Matthews by himself outweighs everything. But some of the choices here were a little hard to fathom; Yegor Korshkov is doomed to be complained about every time he comes up because he was picked over Alex Debrincat, Sam Girard and others. Keaton Middleton and Nicolas Mattinen are both big defencemen who had minimal production and iffy speed. Carl Grundstrom is shaping well, but the remaining nine picks apart from him and Matthews may not produce any NHL players. It’s early yet, still, but some guys are pretty clearly not going to make it.

June 25, 2016: The Kerby Rychel Trade

Minutes after the draft ends, the Leafs trade D Scott Harrington to the Columbus Blue Jackets for F Kerby Rychel and a conditional 5th-round pick. The condition was that if Harrington were waived and claimed by another team, the the Jackets would get the pick; otherwise, no pick would move. The condition was not triggered, so it’s just Harrington for Rychel in hindsight.

One-line summary: A defenceman the Leafs weren’t going to play for a winger the Blue Jackets were tired of.

Significance: Very minor.

Difficulty: Eh.

Quality: It’s fine? Scott Harrington is a depth LD and Kerby Rychel is a power forward who just can’t quite seem to stick in the NHL. Rychel is now gone to Montreal after a year and a half with the Toronto Marlies.

July 1, 2016: The Matt Martin Signing

The Leafs sign unrestricted free agent F Matt Martin for four years at $2.5M AAV.

One-line summary: The Leafs wanted a good player to be both a locker-room presence and an on-ice enforcer.

Significance: Less than the amount of chatter it’s received, but at the same time: Martin cost probably $1.5M more than an equivalent player annually, he got term into years where the Leafs will want all the cap space they can get, he led to the Leafs protecting him in the draft over maybe-an-NHLer Brendan Leipsic, and he blocked other wingers who might have benefitted from playing on the fourth line. They may unload the cap hit this summer, it’s fair to note; the deal is structured so that in the last two years much of the salary is paid in July 1st signing bonuses.

Quality: The things that are easily quantifiable that Matt Martin does are not worth his contract. The benefits of an enforcer, sorry, are mostly make-believe. He’s a decent 12th forward.

Beyond that? He was a good guy and I think he helped out, but if you let them, people will spin you tales about how without Matt Martin and Matt Martin specifically, Matthews and Marner would have started skipping practice to do heroin. I think the simple answer is the Leafs expected to be bad for a few years, and they were therefore okay paying a premium for good-in-the-room guys on a bad team. I get that. I don’t like the deal, but I get it.

July 2, 2016: The Roman Polak Signing

The Leafs sign UFA D Roman Polak for one year at $2.25M.

One-line summary: Polak back.

Significance: Not a ton. It’s a lot of money for a 3RD, but as with Martin, I don’t think the Leafs thought they would be making the playoffs in 2016-17, and they had the money to spare. Polak is a good player, good man, does it right every day and so on, so you can see why Babcock liked having him on a young squad.

Difficulty: Surely no one was bidding this high on Polak, right?

Quality: Maybe better than it seemed like? Polak was actually kind of effective down the stretch (his shot results were better than you may think in the second half of the year.) I complained about him a lot at the time, but with hindsight, this deal doesn’t seem that bad. Possibly because the guy he was displacing was Frank Corrado.

August 22, 2016: The Jhonas Enroth Signing

The Leafs sign G Jhonas Enroth for one year at $750K.

One-line summary: Leafs sign a cheap backup goalie.

Significance: More than I would have liked. Backups tend to matter a lot only when they do really poorly. Unfortunately, that’s what happened to Jhonas.

Difficulty: None.

Quality: Honestly, it was a totally reasonable gamble. It just didn’t work out. Enroth made it into six games and finished with an .872 save percentage, the worst of his career. We wound up trading him (see below) and now he plays for Dynamo Minsk in the KHL. Fun fact: Minsk had Ben Scrivens and then Jhonas Enroth as its starting goalies in successive years.

October 24, 2016: The Ben Smith Waiver Claim

The Leafs claim C Ben Smith on waivers from the Colorado Avalanche.

One-line summary: The Leafs get a quality AHL centre who can take faceoffs, because they don’t trust Peter Holland at 4C (see next transaction.)

Significance: More than it should have had but less than it seemed like. Ben Smith played 36 games for the Leafs, had four points, got slaughtered in CF%, and made people mad.

Difficulty: Waiver claims are easy. I could do a waiver claim if you told me where to send the form.

Quality: I mean, it’s a waiver claim, so eh, and centres don’t grow on trees. I didn’t love it, though; it just made it easier for Babcock to turf Peter Holland. But oh well.

December 9, 2016: The Peter Holland Trade

The Leafs trade F Peter Holland to the Arizona Coyotes for a 2018 conditional sixth-round pick. The condition was that the Coyotes re-sign or trade Peter Holland. They did neither, so the Leafs wound up with nothing.

One-line summary: The Leafs trade a depth C their coach wouldn’t play for a chance at a pick.

Significance: Very minor.

Difficulty: I’m pretty sure this is the best they were gonna get.

Quality: Something for nothing is not a great trade, though the Leafs were pretty well boxed in when Mike Babcock made it clear he preferred AHL C Ben Smith as his NHL 4C over Holland. You can argue Lou did well to wind up with at least a chance at another asset rather than just losing Holland on waivers. Holland is also kind of an NHL/AHL tweener, so he’s not a huge loss, but I’ll allow myself a little bias here. I don’t like this trade.

January 11, 2017: The Jhonas Enroth Trade

The Leafs trade G Jhonas Enroth to Anaheim for a 2018 7th-round pick.

One-line summary: The Leafs’ backup crashed and burned, so they got a low pick for him and replaced him with a guy off waivers.

Significance: Meh.

Difficulty: You probably have noticed by now that Lou likes to get something for every asset, by God. From an asset management perspective, this is a willingness to make sure you don’t lose an opportunity at a pick ever, and as a consistent practice it’s a little impressive.

Quality: Enroth wasn’t going to do any more in Toronto, so getting anything for him is fine.

January 11, 2017: The Curtis McElhinney Waiver Claim

The Leafs claim G Curtis McElhinney on waivers from the Columbus Blue Jackets.

One-line summary: Out with the old backup, in with the new backup.

Significance: It wound up being pretty key! Curtis McElhinney famously came in in emergency relief of Frederik Andersen in the game the Leafs clinched a spot.

Difficulty: Well, it’s sort of in conjunction with the Enroth thing, but it’s just a waiver claim on its own.

Quality: It’s hard to argue with the results. McElhinney has been as good a backup as the Leafs could have hoped and they got him for an SPC slot.

February 4, 2017: The Alexey Marchenko Waiver Claim

The Leafs claim RD Alexey Marchenko on waivers from the Detroit Red Wings.

One-line summary: The Leafs claim a 7D; simultaneously with this, they waive Frank Corrado, who Mike Babcock clearly did not trust to play NHL minutes.

Significance: Very little. Marchenko was RD injury insurance, but it would have taken two Leaf D injuries to get him into a high-leverage game. During the playoffs, the Leafs lost first Nikita Zaitsev and then Roman Polak when Zaitsev came back, and Mike Babcock elected to play Martin Marincin and Connor Carrick over Marchenko. Marchenko is now in the KHL; he recently won an Olympic gold in men’s hockey as one of the Olympic Athletes from Russia.

Difficulty: Zero.

Quality: Eh, I think it was worth doing. The Leafs had an RD Mike Babcock was not interested in playing, so they brought in one he knew from the Red Wings (Marchenko did play 11 regular season games for Toronto down the stretch—more than Corrado did all year.) It was low risk, low reward, but I’m fine with it.

February 27, 2017: The Brian Boyle Trade

The Leafs trade F Byron Froese and a 2017 2nd for F Brian Boyle.

One-line summary: A surprise playoff contender, the Leafs pay for their dream 4C as a rental.

Significance: Maybe less than it seems like, but for a team 10 months out of finishing last to be buying a depth rental is a pretty wild change.

Difficulty: I suspect the Bolts were pretty happy with their rental return.

Quality: From an asset management standpoint, not great. The Leafs paid for a rental in a year they were iffy for a playoff spot and likely to lose in the first round, and then they made the playoffs and lost in the first round. Then Boyle signed in New Jersey. But...Boyle unquestionably improved the Leafs fourth line, he helped them make that series, and he gave this team and these players a taste of the playoffs. I can’t quite condemn this one.

March 1, 2017: The Frank Corrado Trade

The Leafs trade D Frank Corrado to the Pittsburgh Penguins for F Eric Fehr, D Steven Olesky, and a 2017 4th.

One-line summary: Inexplicably, the Leafs trade franchise defenceman Frank Corrado for a bad contract, an AHL defender, and a 4th.

Significance: Well, it helped people stop talking about Frank Corrado. Really this was a lot like the Leafs taking on Fehr’s contract for a 4th, and Corrado was just sort of there.

Difficulty: Judging by the fact we waited so long to trade Corrado, maybe a lot? But this is a pretty normal return. Corrado had previously cleared waivers, it’s worth noting, which helped.

Quality: Fine? The Leafs got a pick for a guy they weren’t using, they could afford Fehr, and then they turned Fehr into another pick. Works for me!

May 2, 2017: The Nikita Zaitsev Extension

The Leafs extend their own RFA, RD Nikita Zaitsev, for seven years at an AAV of $4.5M.

One-line summary: The Leafs’ most controversial signing, likely, as they pay a premium to lock up their guy.

Significance: Potentially a lot. Potentially a lot in a bad way.

Difficulty: The thing is, Lou Lamoriello knows how to leverage RFA status, but he was in a spot here for two reasons. One, it would be very easy for Zaitsev to return to the KHL, and two, the Leafs were absolutely barren in right-shooting defencemen after Zaitsev. On the one hand, they paid a premium here, on the other, this would have been thinning out the exact position they most needed to add to. You can easily see why they did what they did.

Quality: The Lamoriello front office has prized flexibility greatly. Zaitsev is signed two years longer than anyone else on the team, and he’s not coming cheaply. It’s worth noting that at some point Zaitsev might return to Russia and the contract would disappear (and that the deal should avoid any recapture penalty), but you can’t sign a guy to a seven-year contract for a lot of money and expect he isn’t going to collect it. I’m not sure the Leafs could have realistically let Zaitsev go, but this is the deal that worries me. If he’s struggling in a second-pair role and we can’t fix that, well, this contract will haunt us.

June 18-20, 2017: The Vegas Golden Knights Expansion Draft

The Leafs chose to protect: F Tyler Bozak, F Connor Brown, F Nazem Kadri, F Leo Komarov, F Josh Leivo, F Matt Martin, F James van Riemsdyk, D Connor Carrick, D Jake Gardiner, D Morgan Rielly, G Frederik Andersen. The Vegas Golden Knights claimed F Brendan Leipsic.

One-line summary: Pretty much the sole controversy in this list was to protect Matt Martin as opposed to Leipsic, a forward prospect who had been doing well with the Marlies.

Significance: Right now, it doesn’t seem like much. The Leafs have a huge log-jam at wing right now, and Leipsic has thus far only been a fringe NHL player. Vegas wound up dealing him to Vancouver at the deadline.

Difficulty: Just a choice of who to lose, really.

Quality: I hate to belabour the Matt Martin thing, but I would rather have Brendan Leipsic than Matt Martin’s contract even if I thought Martin were more useful, and I don’t. I don’t think this is a crippling error or anything, but it’s a follow-up to the Martin signing.

June 23-24, 2017: 2017 NHL Entry Draft

The Leafs drafted: D Timothy Liljegren (17th OA), D Eemeli Rasanen (59th OA), G Ian Scott (110th OA), F Vladislav Kara (124th OA), D Fedor Gordeev (141st OA), F Ryan McGregor (172nd OA), D Ryan O’Connell (203rd OA.)

One-line summary: The Leafs pick the year’s big faller in round one and continue their preference for big defencemen.

Significance: Potentially immense!

Quality: It’s way, way too early to tell. I will say I loved the Liljegren pick at the time, as did pretty much everyone I know, and I’ve been very pleased with his development since. Some of the picks were a little more confusing (Scott and Kara) but I give a lot of room to the scouts, as ever. Also, Gordeev is cool.

May 16, 2017: The Borgman and Rosen Signings

The Leafs sign Swedish free agent defenders Andreas Borgman and Calle Rosen to two-year ELCs.

Significance: Borgman might be something. Rosen has, to my sorrow, not really made the jump, but you never know.

Difficulty: Another case where the Leafs’ efforts in Europe paid dividends. Encouraging to see.

Quality: Given these were both very low-risk gambles, I don’t see how you can be anything but pleased with these signings. Borgman has shown flashes in the NHL of being a physical, effective defenceman and there’s some chance he could eventually be top-four calibre. Rosen is currently in the AHL and may wind up back in Sweden, but betting on defenders who can skate is always fine by me.

July 1, 2017: 2017 NHL Free Agency

The Leafs sign veteran LHD Ron Hainsey as a UFA, for two years at a $3M AAV. They add Dominic Moore for one year at $1M and sign Patrick Marleau for three years at $6.25M AAV. They extend backup goalie Curtis McElhinney for two years at $850K.

Four-line summary: The Leafs don’t find a big acquisition to their liking, so they shore up their defence on a budget (Hainsey). They get a bargain-bin 4C at a low price (Moore). They pay quite heavily for an old but quick star LW in Patrick Marleau. And they go with their faithful backup option in McElhinney.

Significance: High. Hainsey has played top pair for us most of this year and, while that’s not ideal, he may end up doing so again if we can’t upgrade this summer. Moore has been mediocre and the Leafs paid to replace him, but he’s a better bet than Frederik Gauthier and he was extremely affordable. Patrick Marleau is now the Leafs highest-paid player (!)

Difficulty: It’s only money, darling.

Quality: Hainsey: pretty good. Hainsey’s shot results have fallen off recently and playing an aging LHD as your top right defenceman is not ideal, but he’s done fine for a reasonable price and will likely do so again next year. We ought to make an acquisition to bump him down but I don’t have a problem with this deal at all.

Moore: fine. He was a reasonable acquisition for a reasonable price.

Marleau: I...don’t know. Marleau is still a good player (he’s already got twenty goals this year) and I didn’t mind getting him. But the fact remains he is making a hell of a lot of money and he probably isn’t about to get any better at age 38. If the Leafs don’t need his cap space in the third year or they find some way to unload it, this will be okay. The contract may have been structured with this in mind—Marleau gets a big signing bonus to start the last year and then remaining actual cash owing is $1.25M for the final season. But keep in mind Marleau is almost superhumanly healthy, he has a full NMC, and the Leafs don’t benefit from either buying out or Marleau retiring out of a 35+ contract. This one may sting come free agency 2019.

McElhinney: I was a little worried about this and honestly I was worried for nothing. McElhinney has defied his career norms and put in an excellent backup year. Does he look like, as Jared put it, a wacky inflatable tube man and Dominik Hasek are fighting for control of his body? Yes! But it works. If we replace him with Calvin Pickard next year, whatever, his salary is no obstacle.

Summer 2017: The Zach Hyman and Connor Brown Extensions

The Leafs extend RFA wingers Zach Hyman and Connor Brown. Hyman gets four years at $2.25M AAV; Brown gets three at $2.1M.

Significance: Pretty meaningful. Having an affordable, but effective, supporting cast is important for a team that’s going to have multiple expensive deals before long.

Difficulty: As said before, RFA negotiations favour the team strongly. Not a freebie, but still.

Quality: I think the Zach Hyman deal is excellent for what he brings. The Brown deal isn’t a problem or anything, but I don’t love his numbers quite as much. Still, I’m fine with these contracts.

October 6, 2017: The Calvin Pickard Trade

The Leafs trade Tobias Lindberg and a 6th-round pick to the Vegas Golden Knights for G Calvin Pickard.

One-line summary: The Leafs trade minimal futures for a good goalie who had already cleared waivers.

Significance: Potentially more, down the road.

Difficulty: Probably not a lot, but nice touch getting Pickard after he cleared waivers and getting more certainty on the asset; it meant the Leafs could demote Pickard to the AHL risk-free.

Quality: Excellent. Pickard looks like a legit NHL backup, or maybe better, and he’s doing very well in the AHL. Lindberg has since already been traded again, and I don’t think he’s going to do much.

October 23, 2017: The Roman Polak Signing, Mk. II

The Leafs sign UFA D Roman Polak for one year at $1.1M AAV.

One-line summary: Polak back again.

Significance: It made Mike Babcock happy and many bloggers sad. In the grand scheme of things, not a ton.

Difficulty: No one was bidding against us and he was already practicing with the team.

Quality: Polak is a 7D now. I strongly suspect this signing was at the behest of Mike Babcock. I think maybe people blow this one a little out of proportion—he has okay PK stats and his expected goals percentage at 5v5 is 49.4% adjusted, which is really not bad for a third-pair guy. But he takes too many penalties and I’d rather play Connor Carrick. Still, I don’t think this signing was necessary.

November 7, 2017: The Josh Leivo Extension

¯\_(ツ)_/¯

February 15, 2018: The Nikita Soshnikov Trade

The Leafs trade F Nikita Soshnikov to the St. Louis Blues for a 4th.

One-line summary: After extensive roster shenanigans, the Leafs finally get a return for a player who was approximately their 14th forward.

Significance: Not a lot.

Difficulty: Another case of Lou waiting as long as possible to get a return on assets; some of the stuff with Soshnikov sure looked like the Leafs were using injured reserve to evade waivers. Rules are for other teams.

Quality: Honestly, I think this was the best the Leafs were likely to do for a player they couldn’t play who had a 0.2 points per game in the NHL for his career. Some people seem to have expected more based on how much they liked Soshnikov and their idea of his potential (keep in mind he’s already 24), but I don’t think that was realistic.

February 20, 2018: The Eric Fehr Trade

The Leafs trade F Eric Fehr to the San Jose Sharks for a 2020 7th-round pick.

One-line summary: Eric Fehr was already almost all the way out of the Leafs organization, considering he was loaned to another AHL team, but Lou got a pick for him anyway.

Significance: Almost zero.

Difficulty: See what I mean about the guy scooping up late-round picks for fringe assets? I’m surprised more of the nerds don’t love Lou, because he’s relentless in chasing some kind of ROI for every player he can.

Quality: More than happy with this.

February 25, 2018: The Tomas Plekanec Trade

The Leafs trade F Kerby Rychel, D Rinat Valiev, and a 2018 2nd-round pick to the Montreal Canadiens for F Tomas Plekanec and F Kyle Baun. The Canadiens retain 50% of Plekanec’s salary.

One-line summary: For the second straight year, Lou pays a 2nd for a 4C rental, this time with a bit of AHL flavour mixed in.

Significance: So-so.

Difficulty: Centres aren’t cheap and Plekanec is luxury depth, but the Habs were primed to sell. Renting 4Cs every year is a bit of an awkward habit to get into, and yet I don’t blame Lou for riding with Dominic Moore in the summer.

Quality: Okay, once again. Valiev and Rychel, as an LD and a wing, were both thoroughly blocked in the Leafs’ organization, while Baun is AHL depth with a cool name. Plekanec definitely makes the Leafs better; whether you’re happy paying a 2nd to make a moderate improvement in a year the Leafs have maybe the seventh-best chance at a Cup is a philosophical thing.

Conclusions

Lou has read the rulebook: They’ve extensively used LTIR and injured reserve, they fought and won the Cowen buyout, and above all, they’ve taken their sweet time. Brandon Pridham is, I’m sure, invaluable at this, but Lou is the Godfather, and he’s gotten away with all of it. The closest the league game to acting against Toronto was the Lupul LTIR evaluation, which the Leafs passed easily.

They’ve extensively used LTIR and injured reserve, they fought and won the Cowen buyout, and above all, they’ve taken their sweet time. Brandon Pridham is, I’m sure, invaluable at this, but Lou is the Godfather, and he’s gotten away with all of it. The closest the league game to acting against Toronto was the Lupul LTIR evaluation, which the Leafs passed easily. Lou is clearly big on asset management: did you notice how many trades the Leafs made for seemingly low-value assets where they got a late pick back? Fehr, Enroth, Soshnikov, Corrado, and a hope of one with Holland? In several of those cases, Lou hung onto the players even with no intention to play them for months; in Soshnikov’s case, he stretched the use of injured reserve to the limit to do it.

did you notice how many trades the Leafs made for seemingly low-value assets where they got a late pick back? Fehr, Enroth, Soshnikov, Corrado, and a hope of one with Holland? In several of those cases, Lou hung onto the players even with no intention to play them for months; in Soshnikov’s case, he stretched the use of injured reserve to the limit to do it. Lou likes his options: My description of Lou’s management ethos is “give me optionality or give me death, or a third alternative to be named later.” He definitely is willing to wait and to keep as many options as possible in hand when dealing with players.

My description of Lou’s management ethos is “give me optionality or give me death, or a third alternative to be named later.” He definitely is willing to wait and to keep as many options as possible in hand when dealing with players. Related point: I don’t know if this means much, but given Lou’s tendency to work the system: the three most potentially troublesome signings the Leafs have are Martin, Marleau, and Zaitsev. The former two are constructed so they’re easier to trade at the end (if Marleau will waive his NMC) and the latter may potentially disappear if Zaitsev goes back to the KHL. Hmm.

Lou worked very aggressively to acquire picks early in his tenure. He’s less fixated on that now, naturally enough, but Lou deserves some credit for finishing the tear-down portion of the rebuild in pretty much complete fashion. He also cleared out the Phaneuf trade.

He’s less fixated on that now, naturally enough, but Lou deserves some credit for finishing the tear-down portion of the rebuild in pretty much complete fashion. He also cleared out the Phaneuf trade. Taken together, I think Lou did a good to excellent job finishing the first stage of the rebuild. His drafting work is mostly TBD. but I think Lou’s first season (July 2015 to June 2016) was close to the ideal rebuild season.

His drafting work is mostly TBD. but I think Lou’s first season (July 2015 to June 2016) was close to the ideal rebuild season. Lou’s work in the two years since has mostly been more cautious and is more ambiguous. What stands out is what’s not there: there’s no trade for a top-pairing D. The Leafs didn’t trade for any of their top nine forwards (when healthy) nor any of their top four defencemen as currently constituted. We’ve heard strong suggestions they pursued some defence candidates—Travis Hamonic, Chris Tanev, Ryan McDonagh—but they never closed any of the deals. As Lou transitioned the team to the second stage of the rebuild, he’s been more hesitant to make a big trade. All we have are rental 4Cs and FA signings. The positive spin is that Lou has only done two things that are even potentially big mistakes—the Zaitsev and Marleau signings—and neither of those is a capital-B Bad Contract of the kind that the Leafs have had in the past.

Let’s break it down by type:

Trades: Lou has made 19 trades in his Leaf tenure and, while most of them were minor, the worst of them is probably Panik for Morin, which is pretty trivial. His biggest trades—the Phaneuf and Andersen deals—stand as clear successes. Unless you strongly object to the 4C rentals, and I see why you might, I think Lou’s trade record is very respectable. (He got two seconds for Polak and Spaling!)

Lou has made 19 trades in his Leaf tenure and, while most of them were minor, the worst of them is probably Panik for Morin, which is pretty trivial. His biggest trades—the Phaneuf and Andersen deals—stand as clear successes. Unless you strongly object to the 4C rentals, and I see why you might, I think Lou’s trade record is very respectable. (He got two seconds for Polak and Spaling!) Drafting: The Leafs’ draft record under Lou is ambiguous, and you can complain about individual picks. On the other hand, the picks that haunt you the most are missing with your first-rounders, and both Matthews and Liljegren are just dandy for where we got them. But if the Leafs wind up without much from the sixteen picks after the first round that they’ve made under Lou, some of his lustre will dim a little with time. (Or people will just blame Mark Hunter, idk.)

The Leafs’ draft record under Lou is ambiguous, and you can complain about individual picks. On the other hand, the picks that haunt you the most are missing with your first-rounders, and both Matthews and Liljegren are just dandy for where we got them. But if the Leafs wind up without much from the sixteen picks after the first round that they’ve made under Lou, some of his lustre will dim a little with time. (Or people will just blame Mark Hunter, idk.) European FA Signings: I think these deserve their own category. It’s a bit of a playing-with-house-money situation here since these are low-risk ELCs, but I think the Lamoriello regime deserves credit for cultivating European pro players and landing them. Zaitsev and Borgman’s initial deals are great additions.

I think these deserve their own category. It’s a bit of a playing-with-house-money situation here since these are low-risk ELCs, but I think the Lamoriello regime deserves credit for cultivating European pro players and landing them. Zaitsev and Borgman’s initial deals are great additions. RFA Signings: Mixed bag here. Some of these are so, so good (Kadri and Rielly), some are good (Hyman and maybe Brown) and one of them is Zaitsev (tension mounts.) I still think the Zaitsev deal is more of a potential problem than a present one, and I still have some hope that his results can improve to match his obvious skills. The Zaitsev deal stands out especially because Lou has done so well with his other extensions.

Mixed bag here. Some of these are so, so good (Kadri and Rielly), some are good (Hyman and maybe Brown) and one of them is Zaitsev (tension mounts.) I still think the Zaitsev deal is more of a potential problem than a present one, and I still have some hope that his results can improve to match his obvious skills. The Zaitsev deal stands out especially because Lou has done so well with his other extensions. UFA Signings: I don’t like the Martin deal and I worry about the end of the Marleau deal, but Lou has generally been cautious about giving term deals with big cap hits to UFAs, and as a result he’s mostly stayed out of trouble on this front. Big, lengthy UFA contracts (see Clarkson, David) are a time-tested way to wreck your cap sheet, and Lou hasn’t had one. Of course, the real temptation to sign one is going to come when the Leafs seem close to real contention...

I don’t like the Martin deal and I worry about the end of the Marleau deal, but Lou has generally been cautious about giving term deals with big cap hits to UFAs, and as a result he’s mostly stayed out of trouble on this front. Big, lengthy UFA contracts (see Clarkson, David) are a time-tested way to wreck your cap sheet, and Lou hasn’t had one. Of course, the real temptation to sign one is going to come when the Leafs seem close to real contention... Development: We’re getting into murkier territory here, and yet it does matter how the team develops its players. It’s hard to know how to apportion credit or blame to Lou for this, and you could just as easily say Lou had very little work to do in developing the prodigious talents of Matthews, Marner and Nylander, or that the credit there goes to Babcock. But at least so far, Lou has headed an organization that appears to work cohesively and that has done well with its key players. There are also signs of clear investment at every level, even to the point of sending specific coaches like Stephane Robidas and Barb Underhill to work with junior prospects like Keaton Middleton and Eemeli Rasanen. These things, and many others, are made easier by the Leafs’ ample resources, but it nonetheless is creditable that Toronto is leveraging those resources to the full. At the least, Lou’s FO passes the test of “apparently better developmentally than the Oilers.”

So after this long, long survey:

One-sentence summary: I think Lou Lamoriello has done a good job.