Thought he was just fine. A goal away from the peak of this core so far which is a second round appearance but you can't predict Nylander suddenly experiencing migraines the day before the postseason starts, Matthews getting injured, or your top goalie and reason it even went to 7 injuring himself in the last second of Game 6. Looking at his overall body of work there were a few errors but most of his moves were on the positive end.
His first mistake was keeping that idiot Keefe who had by this time last year proven he didn't have it in the postseason. I suppose he didn't want to rock the boat too much but that mindset should've only been reserved for keeping the core players (which he did), not holding on to a coach who had by this point proven he couldn't strategize his way out of a wet paper bag. Second was not trading Marner before his NMC kicked in. He either didn't want to make such a deal in such little time without knowing this team or all the facts or Shanahan forbid it. Either way it's hard to blame him for not moving on such a monumental change when he was so new, but given this franchises current predicament it's still worth mentioning.
First few free agent signings were head-scratching to say the least. Re-signing Kampf to that AAV and term was dumb then and it's dumb now. I can understand being worried about centre depth after ROR told the organization to get stuffed but Kamp was and is nowhere near worth that. Klingberg and Reaves were also not good. Reaves at least carved out a role for himself and was semi-effective on the ice, Klingberg was an issue from Game 1 and while we now know the reason why it still wasn't a great signing. Lagesson and Lajoie were solid D-depth so not much to complain about there.
The next few free agent signings are where he really started to shine and make up for things. Bertuzzi and Domi were brought in for secondary offence and grit and they both did good in their roles. Took a while for them to get going since Keefe had zero idea how to utilize them to start (unless you're a core player or a vanilla player who's safe defensively Keefe doesn't seem to know what to do with you). Martin Jones was a great 3rd stringer, Benoit was a revelation and is the type of glue guy this team needs, and Gregor was serviceable as a fourth liner. When it came to free agent signings there was no great, lots of good, and one disaster that thankfully was able to be buried.
Also important to consider who he didn't sign and hold on to as much as who he did sign. While it sucked to lose players like Schenn and Acciari along with ROR I'm glad Treliving didn't give in to their demands and let them walk. Benoit plays the Schenn role well even if he can't play beside Rielly, and while Acciari is effective you want someone younger to play his role, his age makes me weary to commit the term and money he got from Pittsburgh. Would've liked to have kept Gustafsson instead of signing Klingberg but Keefe didn't seem to like him or use him last season and postseason. Holl was addition by subtraction. Bunting I'm still not sure if I would've liked to have back, great pest and skilled but if the refs were gonna continue to treat him like shit here he wasn't going to be too effective. Bertuzzi and Domi play heavier and Domi also has the added advantage of being able to play centre. Maybe could've used the Klingberg money on Bunting but with the amount of wingers upcoming in the system it's not that massive of a loss and it's better that we have that cap-space for a defenseman or a goalie.
As for trades, again I think he was fine, he played it pretty safe in this regard. Lafferty was an early one that a lot of us maligned due to Lafferty starting hot (of course) and Reaves looking like a below-replacement level player. Ultimately it didn't matter as Lafferty proved his futileness in the playoffs again with Vancouver and the Leafs upped McMann and acquired Dewar who play a similar role. Really our bigger issue with this whole drama should've been the fact that the Leafs re-signed Kampf to that ridiculous contract when Lafferty was already in the fold and could play centre. I'm going to assume Keefe got in Treliving's ear and stressed Kampf's importance given how much he relies on him, God forbid he goes a season without one soft tweener whose defensive capabilities are overexaggerated.
At the TDL, I personally was more than okay not taking big swings like in years past and dealing another first round pick or any of our higher-end prospects for more rentals or guys who would supposedly put us over the top. Lyubushkin performed well with Rielly in the playoffs, Edmundson was fine in a bottom-pairing role and brought it physically, and Dewar looks like he'll be a serviceable bottom-six defensive specialist and is young enough to still improve and grow with the team. None of these guys were Hanifin or Tanev or Walker or Guentzel or Lindholm but this team didn't show they were worthy of spending big on trade additions this season, nor has it helped them much in the past anyway. And when you get down to it none of these guys cost us in the playoffs and if anything had a bigger positive impact than negative. The Cade Webber deal may become a minor stroke of genius but we'll see how he develops.
I like his re-signings of McMann and Benoit. The Nylander and Matthews contracts are also fine, no discount from either of them of course but at this point expecting that of them is a pipe-dream, that ship sailed long ago thanks to the last administration. Holmberg deal was good but only makes the question of why we signed Kampf more head-scratching. Going to arbitration with Samsonov was fine, wish the arbitrator ruled more in our favour but whatever, at least he didn't commit long term to Samsonov and his money can go towards a more stable goalie.
All in all I'd give him a "B" for the 2023-24 season. Majority of his signings worked, he didn't get sucked into trading another chunk of this team's future for a two week postseason, and he did what he set out to do which is change the culture of the team. People may laugh but it does mean something that this team finally showed a good level of pushback and aggressiveness not seen in years. Better to go down in 7 swinging than how this team usually did, which is completely wilting and getting bullied along the way. It will pay dividends in the future when instead of cowering and nervously laughing guys like Knies, Cowan, Minten, Robertson, and Benoit will show some fight instead.