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Did Kent Hughes and Jeff Gorton do a good a job on the deadline deals last month? If you read the various articles and opinion pieces online, the answer is a resounding yes. And it’s pretty tough to beat the return when you look at a summary of results.

But when you take a step back and look at the trades and market, I think these were all pretty easy decisions.

First off, consider having Ben Chiarot, Brett Kulak, Alexander Romanov, and Joel Edmundson in the lineup and upcoming prospects in Jordan Harris, Kaiden Guhle, and Mattias Norlinder all playing left defence. It’s pretty obvious the Habs have too many left-shot defenders. Given the ages and upcoming UFA status of Chiarot and Kulak, they were the obvious ones to go. Everyone including my dead grandmother predicted they would be traded. Absolutely Hughes got a great return but I suspect they were still pretty easy conversations given the limited options available for left defencemen.

Now let’s consider team depth on the wings. They have Mike Hoffman, Jonathan Drouin, Paul Byron, and Rem Pitlick on the left and Brendan Gallagher, Josh Anderson, Joel Armia, and Cole Caufield on the right. The prospect pool isn’t as deep but potential bottom-six depth options include Rafael Harvey-Pinard and Jesse Ylonen. Overall, it’s pretty reasonable depth on the wings. Given his low cap hit and the RFA status of Artturi Lehkonen combined with the existing depth, again we find that trading Lehkonen wasn’t a surprise. Again, the limited defensive forward options available at the deadline worked in Hughes’ favour and he got a great return.

But overall, these decisions weren’t surprising and probably not that difficult to obtain as the market worked in the Habs’ favour. But the questions that keep popping into my head are:

Why wasn’t Chris Wideman traded? Or Tyler Pitlick? Both are UFAs at the end of the year. Were there no offers whatsoever? Did Hughes make any effort to even get a seventh-round pick? Did he try to package them with any of the other trades to squeeze for a better return?

What about Jake Allen? With so many teams looking for goaltending upgrades and with limited availability of good performing goaltenders (i.e. Marc-Andre Fleury) there must have been a market. As an upcoming UFA Fleury got the Blackhawks a conditional second-round pick. With another year on Allen’s team-friendly contract, surely another team might have offered something reasonable?

I understand that other players like Armia, David Savard, Drouin, and Jeff Petry are harder to trade during the season due to extended contracts and cap constraints. But then again, Tyler Toffoli was traded with these same challenges. The Habs were under no pressure to trade their best-performing winger who had two more years on his contract. But Hughes and Gorton clearly signaled an urgent rebuild (and fire sale) when they traded Toffoli for well below market value. The Toffoli trade netted pretty close to the same return as Chiarot even though Toffoli has two more years on his contract and can be traded at the deadline in 2024 to recoup most (if not all) of the draft pick value.

So overall, last month’s deadline deals look great but those were the easy ones and I think even my dead grandmother could have gotten those done. But the Toffoli trade and the lack of other movement of players that might be harder to move keeps me on the fence. I am hopeful that in the offseason we’ll see this rebuild move forward aggressively. I’ll reserve my judgment on Hughes and Gorton until after the summer when the real work begins.