I hope this post finds you on your way out the door to enjoying the summer and not hyper-fixated on the Maple Leafs and how they can still make moves X, Y, and Z to be Stanley Cup favourites by September 1st. I’m not even sure the hockey operations department is putting in the hours that some fans do to find these solutions. Margaritas at a waterfront patio is a great way to not shift focus from the fact that one of Nylander, Domi, Holmberg, Kampf, or Minten will be the Leafs’ third line centre this season and there is no money left to replace Tyler Bertuzzi. Shift focus from these distinctively mid-July thoughts instead…

I’m thinking back to when it was well established that Lou Lamoriello had several signings completed but they weren’t announced until August. In a copycat league, it seems entirely possible we see something like that again. Lou might be the most outward example of that practice though the Leafs themselves had plans in place for their pro try out players Noah Gregor and Zach Aston-Reese before they arrived at training camp.

I guess what I’m saying is that the best of who is left in free agency might already be spoken for and while not being huge losses, there are a handful of players still worth considering.

Daniel Sprong is the best offensive talent available if Nick Robertson intends to move on and not sign in Toronto. Sprong is a pretty straightforward replacement. He’s achieved more than Robertson with a few more years experience but lacks the upside of the Leafs winger. If Toronto wants to go the safe route, Sprong could be it.

Tyler Johnson is a player that Craig Berube would have seen a lot of in the Central Division and know how much is left in Johnson’s tank as well as how to possibly deploy him. Johnson should probably be used primarily as a winger but he is another rainy day centre option that the Leafs could use more of.

Oliver Kylington’s relationship with Brad Treliving will probably matter most here and the fact that Kylington is not a Leaf might point to it not being the best match. A high-pressure market like Toronto might also not be a fit for Kylington. All of this (much like everything in this post) is subjective and Kylington might just be more of a tryout candidate than someone who gets signed immediately.

That brings us to Alex Nylander and whether or not the Leafs are ready for a brother act. Nylander’s late-season showing in Columbus should have turned a number of heads but not enough that teams are ready to gamble on the small sample size. It wouldn’t surprise me to know that there is a lowball contract offer from the Maple Leafs. I also expect that Alex Nylander wants to see what is out there first.

At this point, the options come with a fair bit of a risk and would likely require the player to buy into what the Leafs are doing and take less to play in Toronto. If none of them are a fit, it’s also not a loss.

One of the areas the Leafs haven’t addressed this summer is the need for centre depth and that’s where the Flyers might be the perfect trade partner.

With Morgan Frost not being part of John Tortorella’s ideal roster, the 25 year old centre is likely to be playing somewhere else soon enough. Frost’s $2.1M cap hit makes me wonder if that place should be Toronto.

Frost is far from perfect and there is a high likelihood that players who would thrive under Berube are not the ones that John Tortorella is cutting loose. Frost isn’t a towering force to be reckoned with nor is he a feisty pest looking to get under the skin of anyone who crosses his path. Though Frost might be the best available player who the Leafs can afford. That should be enough to seriously consider him.

The fact that the Flyers aren’t going to bring back a huge return on him and they have been primarily looking for prospect/future trade returns in the past couple of seasons also means the Leafs might be able to add to without further subtractions to their lineup. If the Hakanpaa signing isn’t actually a thing, the Leafs have the cap space available right now for Frost.

Frost has two seasons with 40+ points and is close to hitting 20 goals. This is pretty ideal for a 3C, and Frost could sub comfortably in the top six if needed as well if there are injuries to Tavares or Matthews next season.

As reported by Lance Hornby, Kyle Dubas has a new book coming out about his time in Toronto. In the book the Kyle Dubas identifies his biggest mistake as not locking up the core on details as quickly as he could citing increased cost in waiting. My own belief that Dubas made bigger mistakes aside, this seems like a worthwhile way to jump into the core four philosophy and what went right and wrong with it.

As mentioned in the article via a comment from Darryl Belfry, a lot of the fault is linked to the COVID pandemic and the impact on the salary cap. The biggest black swan event imaginable struck at a bad time for the Leafs and that’s not on Kyle Dubas. There are things that are on Kyle Dubas around this and support his thought on not signing the players sooner.

My biggest issue with Kyle Dubas was always his loyalty. He is loyal to a fault personified and there is nothing wrong with having a “Core Four” it just doesn’t need to be the same four players if the contracts are potentially harming the team.

The Nylander contract turned out to be a fair value deal, the Marner one notably less so, but there is nothing resembling a bargain in the Leafs system and Dubas not fostering that buy-in was a miss. Kyle Dubas not being willing to walk away from Marner when his contract asks exceeded $10M AAV was a miss, and not recognizing that the core four are too similar and not adjusting the makeup of the group to reflect something that would allow for something new was a miss.

The core four could have included a defenceman, it could have included a more physical player, and although somewhat of a gamble, it could have included a forward. Variance could work, but we haven’t seen it. While the players have different ways of going about their game, primarily the Leafs core is four offensive skill players that create a Leafs lineup that plays a similar style top to bottom and if you figure out how to play against it, you’ll beat them in a best out of seven series. There’s a reason why the core works in the regular season and not the playoffs and it doesn’t have to do with toughness. It has to do with the lack of variance in the Leafs approach.

If the Leafs go into next season with a Matthews, Nylander, and $10M second line centre, and a $10M defenceman/power forward/goaltender I don’t think you’d receive the same outrage over the core taking up half the cap space. It’s a just particular group thing.

Kyle Dubas not getting deals done at optimal times was definitely a part of it. In the scenario he laid out there was at least going to be potentially enough money left over that Zach Hyman or Nazem Kadri could have been part of the Leafs core as well (or there would have been an option to be more aggressive about finding a defenceman or goaltender).

In hindsight (and often at the time too) there are plenty of things to criticize about the Dubas years, but he is easily the best Leafs GM since the 2005 lockout. What has set him apart from the rest is that he had a clear vision of the team he wanted on the ice and was building towards a specific goal rather than making reactionary adjustments along the way. It’s the mark of a good GM and it’s the traits you see in Bill Zito, Kelly McCrimmon, and Lightning era Steve Yzerman.

Kyle Dubas was always better suited to be a President of Hockey Operations and establishing the vision. The issue with Kyle Dubas is that as a GM he wasn’t capable of winning negotiations or trades to better enable that vision.