I'm not sure picking Wheeler over Laine is a real thing. Certainly it is speculative.
Letting the room fester and sticking with Maurice for too long are related, IMO. Might be considered as 2 parts of the same issue.
I think Lowry was considered as a possible future HC from the time he was hired. It did not seem like an unreasonable thing to try at the time. It didn't take very long to see that it wasn't going to work, but they were not going to fire a second HC in the same season. It was too late by then anyway.
Not trying to justify Chevy here, just critiquing your list.
I see Chevy's biggest faults as things not done, rather than things done. I don't think he has been bold enough, aggressive enough, in pursuing a better roster. This is just my opinion and is in no way provable. You can't judge what didn't happen. I think he has been patient to a fault, literally to a fault. It has helped him avoid some big mistakes while also preventing him from making any big progress.
A more aggressive style risks making mistakes that see your team finish lower in the standings. That pain is mitigated by higher draft picks. When it works, you get a legitimate window of contention and a real chance at winning the cup. Risk averse management leaves you permanently stuck in the mushy middle.
What is your idea about aggressive moves? We have seen him be aggressive at the deadlines in 18 and 19.
The Dubois deal strikes me as an aggressive one but we are seeing the pitfalls of that. Traded a a talented scoring winger (surplus) for a big and physical play driving top center. The down side is that it looks like we are likly only getting 3 years of service because the player wants to walk as a FA.
So the question becomes how aggressive do you really think Chevy can be in this market. I'm sure he's had plenty of conversations with GMs to get good players with limited term left (Stone, Jones etc) only to be told by the player agent that said player wont reup. We know that happened with Stone, killing any chance of a deal there.
If you are looking at a young player with term, how often do those players ever get traded? I can't really recall the last time that happened so expecting to deal for very good talent locked in for a while is not something that you can count on as very few of those players are on the market.
So essentially you are looking at trying to trade for good players with limited term remaining on their deals and trying to convince them to stay. We see how that has worked with Dubois to date.
So with that said I can see why the team holds onto its talented players who have committed to the market and aren't very quick to move them. Through conversations Chevy likely knows he will have a hard time convincing whoever he trades for to stay. I think this is why you see our big trades happen with pieces who don't want to be here like Kane, Laine as there isn't as much risk. Ok well Dubois doesn't want to stay but that is OK because Laine wasn't staying either. Whereas if we traded say Conner for Dubois well you just gave up a player that committed and has 4 years left in his deal for a guy who's leaving in 2.
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