Verbeek just took on Trouba's entire deal and sent back assets. I think there would have been a taker for Matheson - particularly if there was retention. The Habs may not have gotten a ton, but selling high on Matheson seemed obvious last year.
I have already seen people talking about Trouba like this and what you are missing is that a lot of NHL GMs played in the league when the game was much more violent and most rosters had a genuinely malicious player in addition to a goon. Trouba is the near the last of a breed - maybe Romanov is a guy who hits in open ice, maybe Xhekaj is one too, but other than that, it is rare to see young defensemen attempt this sort of hit. By the time these young guys started playing hockey, headhunting had finally been banned at the NHL level.
Matheson, on the other hand, is a guy who has been around for a very long time and who has been undesirable for a very long time. What you're not seeing is that while it feels easy to just sell high on a guy like that ('get the maximum'), it must also feel stupid to trade a guy like that for, e.g., a 2nd round pick and a middling prospect.
What's weird to me is that the Canadiens moved Kovacevic over the summer - and only for a fourth. Montreal was 10 deep on D, but six (Mailloux, Reinbacher, Struble, Xhekaj, Hutson and Guhle) were still waivers exempt coming into the season, and they only had three experienced RD. Assuming everything else played out the same, they could have sent Hutson or Xhekaij down and kept Kovacevic. Or waived Kovacevic once they saw there were six or seven D ahead of him. The insurance seemed well worth a fourth round pick.
Xhekaj is eligible for waivers, he was signed in 2021. I don't think a team in Montreal's position is looking for insurance.
Feels like Montreal (MSL?) actively didn't like him.
This is obviously true, but also they didn't give up anything for him initially. Nothing ventured.
The overall point I'm trying to make is that the bad process is in not recognizing he's good, not in trading him - teams should be trading players that they don't have a spot for. It's been a while since we've seen a Frankie Corrado sort of situation in the league where a younger player is just riding the pine for months, but it's something that should not happen.