If we were looking back at the past two years of Kyle Dubas and grading him on his vision, we’d probably be pretty comfortable with giving him high marks. Taking the team in an exciting, skill driven direction is something that Toronto has been afraid to do for too long. Looking at the 90s Red Wings as a model instead of getting hung up on how to bet Bruins is the right choice, even if it at times it has been a frustrating one.

As we mark the two year anniversary from when Kyle Dubas moved into the big office, it’s worth taking a moment to celebrate some of hits and misses, and acknowledge some of his strengths and shortcomings. After all, what else do we have to do?

Year one of GMing for Kyle Dubas was about finding his footing, but year two was always going to be less forgiving and it has been. The fact that we can’t point to any playoff outcomes in Year 2 certainly hinders any ability to draw conclusions. Of course, that’s boring, so we’ll try and draw a few a long the way.

One of the high marks areas for Kyle Dubas seems to be his approach to the draft. Not only does he seem quite firm in his philosophy of taking the best player available, or at the very least, skilled players, he seems to understand which players will thrive in the Toronto development system, and knows who his staff will be able to work with. Some of this might change a bit now that he won’t have Sheldon Keefe playing a significant role in the development process, but drafting players that will ultimately play for Keefe is definitely an advantage that outweighs Keefe’s move out of the development role as well.

Taking Sandin, and Robertson are easy decisions to like, but finding Der-Arguchintsev, Hollowell, Abramov, Kokkonen, and Abruzzese also are potential later round hits that the Leafs have struggled with recently.

If there’s any criticism of Dubas it might come from his trading down philosophy that can be frustrating for impatient fans like me. Highly touted prospects being available when the Leafs are about to pick and seeing the Leafs move down for someone like Sandin when we are led to believe Bokk will be star is a tough one in the moment, but Dubas has earned some trust there.

He’s also earned some trust last year by finding Robertson in the second round that we should feel a little less worried that the Leafs don’t have a first round pick for the second year in a row, thanks to the Marleau trade (much more on that later).

Provided that Dubas starts keeping his first round picks, and maybe, just maybe considers acquiring more from time to time, it’s hard not to consider drafting to be one of the strengths of Kyle Dubas and team.

We started off pleasantly by mentioning a strength of Kyle Dubas, but let’s move on to one of his weaknesses, and that’s contract negotiating. It may have taken a year but we should all be feeling better about the Nylander contract. It might not be a steal, but it certainly looks like a contract he’ll live up to or exceed his value on. It still remains baffling why this process had to go on for as long as it did, and you’d have to think that 2018-19 could have gone better for the Leafs if it was dealt with sooner, but yeah, Nylander isn’t likely to disappoint again.

The Matthews contact is what it is. It’s certainly not a discount and it’s paying one of the best players in the game what they are worth. The term is disappointing, but at the end of the day the Leafs have Auston Matthews and that’s a good thing.

Mitch Marner is an incredible hockey player, but one with a contract that is an absolute abomination. While fancy little plays off the boards that result in seemingly impossible passes to Tavares and Matthews are wonderful, it’s confusing as hell why Marner is seemingly getting paid $2.5M/yr more than he should to be making those cute little plays and not a lot else. The Marner contract contract cost the Leafs a first round pick by having to package it with Marleau to free up cap space. It resulted in the departure of Jake Gardiner, which led the Leafs to really only being able to replace his absence by bringing in Barrie instead of getting an opportunity to upgrade the blueline. And as a result meant the Leafs downgraded from Kadri to Kerfoot, and from Gardiner to Barrie as a result of overpaying Marner. A big part of the team taking a step backwards this year came from this trade, and it might be the biggest criticism of Dubas to date.

All that being said, Dubas seems to have a set philosophy of paying a premium for an elite core group and surrounding them with the most capable filler that he can muster with remaining salary. If the Matthews, Marner, Tavares, Nylander core is 100% essential and having them feel they’ve been compensated at the level they want to be is important to them being successful, than I guess we’ll have to suck that up and the pressure is on to make sure the rest of the team is filled in well.

Neither Kapanen or Johnsson’s contracts were bargains or overpayments. Justin Holl’s contract might end up being a steal if he can consistently line up in one of the top two pairings. The Engvall could be a steal if he steps up into a top nine role, and while not necessarily great, the Muzzin contract is understandable.

It’s hard not to see this as the biggest flaw for Dubas, and anytime you see a player listed as a pending free agent on the Leafs roster there is a bit of panic associated with how it will be addressed. While I think Dubas has shown that he can make things work, it feels like he makes things harder on himself than he needs to.

The man brought us John Tavares. That’s no small feat and deserves a lot of recognition.

The Jason Spezza and Tyler Ennis signings were also quite inspired, and spending the league minimum on bottom six forward skill makes a lot more sense than the $6M contract that Lou Lamoriello gave to Marleau.

Dubas’ focus on AHL/NHL tweener depth over chasing big names has also been a solid move for an organization that spent years in the habit of overpaying for underwhelming talents like Mike Komisarek, Tim Connolly, David Clarkson, and the previous mentioned Patrick Marleau (who I love, but will concede that it was a bad idea, even at the time.)

You could make the argument that a lot of Dubas’ decisions to be stingy on free agents comes from the lack of flexibility he has left himself from the internal contracts, but that ignores the aggressive acquisition of John Tavares and the somewhat underwhelming 2019 summer free agent pool. Knowing that the Leafs presently look to be backed into the corner for cap space and will probably be for the foreseeable future, it will be interesting to see in some new found creativity emerges.

Hoooo doggy. Is it safe to say that every GM is a mixed bag in this regard, and leave it at that? No? Okay, let’s do this.

This should be celebrated as a win, as the Leafs added a good defenseman, on a good cap hit, and the price of two B prospects and a 1st round pick seems pretty darn reasonable. Having those prospects and pick end up in a different conference is also nice, and then having Dubas hit a home run in the second round by selecting Nick Robertson made the quiet first day of the draft sting a lot less. Having Muzzin re-sign is also a nice little bonus out of the deal, although we might feel less good about that in a couple of years.

Adding Jack Campbell and Kyle Clifford is decidedly less exciting than Muzzin, but so far Jack Campbell looks to be a solid backup on a reasonable cap hit, and Kyle Clifford is a pending free agent, who really hasn’t shown much that would make us want to keep him as a Leaf (playoffs might significantly change that.) Giving up a 2nd for Clifford and Campbell would have been reasonable, the 3rd round pick that has the potential to turn into a 2nd if the Leafs re-sign Clifford is a bit steep.

If Campbell provides good security in net, the steep price will be tolerable.

The Leafs needed a shake up. The Leafs needed a right shooting defensemen. The Leafs would need someone to replace Kadri. This deal seemed like it addressed a lot of things, but ignores the fact that trading Nazem Kadri was a bad idea. Neither Kerfoot or Barrie gave the Leafs enough that this deal ever sat right, and while on paper it still seems like a reasonable move, and possibly a win for the Leafs, it has been anything but.

I have to believe that there would have been a better option than this over time. Someone somewhere would have paid Marleau’s low salary and loved to had his $6.25M cap hit. His No Movement Clause certainly complicated things, and the forced need of a buyout. The fact that no one is available to do Kyle Dubas any favours speaks to his outsider standing with the old boys club, and that will be one of his challenges to overcome until there is more front office turnover around the league. It’s not something to blame Dubas for, but going into a second year without a first round pick, and watching the Leafs struggle this season, this trade leaves a sour taste in the mouth.

It’s hard to imagine acquiring Ben Harpur and Cody Ceci and considering a trade a win, but here we are. The Sens also got the best player in the trade in Connor Brown, but the Leafs escaping Zaitsev’s contract was a win and makes the future a little brighter. It’s also trades like this that give us hope that some more unconventional moves can be made to help keep the Leafs from falling back into a decade of despair.

So the big one here is getting rid of Mike Babcock. Not an easy thing to do, but the absolute right decision. Arguably it was the right decision a year earlier. It was the right decision after the last playoff exit, but politically this couldn’t have been an easy move to sell the organization on, nor one that Dubas can take a lightly as a part time hockey blogger does.

Bringing in Sheldon Keefe makes a ton of sense as well. Whether or not he is the best coach. And whether or not you are now wishing Bruce Boudreau could take over isn’t important. There is a huge benefit from the coach and GM being on the same page and that’s what is happening now. They’ve won together. They know the value in what they bring to the table, and they know what players are going to be brought in and how they are going to be played. This is comforting and will probably be even more comforting after the next training camp.

As for the assistants. That will be interesting situation. McFarland has already left, and it’s hard to imagine that Hakstol is in the long term plans for the Leafs either. Though it will be nice to see a decision being made where both the coach and GM seem to be in agreement.

Beyond that, Dubas seems to have made the most of the unlimited funds at the disposal of MLSE and he has made sure the Leafs have the best people working in all areas of development, research, and sports science.

When it comes to the other stuff, I think we’re back to blindly praising Dubas. He’s got a vision for an exciting, fast paced team that markets itself as fun and removes a lot of the stuffy tradition more befitting of a team that isn’t over 50 years removed from success. He’s taken the best parts of the Lamoriello mentorship, by making sure the organization remains tight lipped about it’s actions, the ability to maneuver league rules creatively, and done away with the unnecessary rules about low numbers, facial hair policing, and not letting players have an identity.

He’s made sure the talent pipeline stays flowing, even when the organization is without a first round pick, and has established a core roster that should keep the playoffs a reality for Toronto for at least the next half decade. Generally Dubas has been a success.

A big part of him being a success is his vision, even if it’s a rather slow moving vision. And it’s hard to imagine we’ll even get a concrete understanding of where we are at the end of this season, which could lead to exploring what the Leafs have today before showing an interest in tweaking his approach. His patience can be frustrating, but it’s probably more of issue with where he’s managing than anything else.

Being ready to win a championship within two years is a ridiculous ask, but unfortunately for anyone in charge of Toronto it’s going to be perceived as the organization already burning through 53 years of time getting to where we are today. The Raptors winning a championship recently doesn’t help with the amount of pressure on Dubas either.

So perhaps what we can take away from the first two years of Dubas is that for the most part we should be happy with where he’s taken the team. We should feel comfortable that he’s a GM not afraid to make bold moves and think differently. We should recognize that like any GM, Coach, Player, Mascot, Fan, he’s going to do frustrate us from time to time, but ultimately he seems to be good for the Leafs, and it’s safe to remain optimistic about what will come next.