For me there are three really miserable weaknesses in our management to this point.
1) cap management. We have 13mil in dead space. That's 13mil that could not be used to adjust the roster so that either the kids who are not ready would not need to be rushed in or so that players could be added to supplement the kids' particular games. A Granlund or Haula would've been great adds in this respect. Aside from the dead space, we have continued to commit a ton of money to players who aren't worth the paycheck. I like Trouba more than most, but he was never worth nor going to be worth 8mil X 7. That contract was a joke and will be a huge obstacle to us moving forward. Kreider's is more reasonable to me since it was a discount, it was made worse by an unpredictable flat cap, and we didn't know we'd get Lafreniere and be so flush at LW.
2) The treatment of veteran players. Zuccarello, Hayes, and Fast all really wanted to be Rangers. Of course, you can't keep them, but all reports say that we completely refused to communicate with the players/representation about either possible extensions, or our fixed decision to move on from them. All three have expressed some level of disappointment/betrayal about the way they were treated. And that's before even mentioning Henrik Lundqvist--maybe the greatest Ranger ever--who we sat as a third string goalie for two months before buying out. That was nauseating to watch last year. Especially considering the player we were prioritizing in Georgiev. You want a good culture, players that are committed and care about this organization: but these things don't go unnoticed.
3) We have had four straight picks in the top 10, and two straight in the top 2. None of them have even remotely performed up to par with expectations. You can say that that's us fans all overhyping them or getting impatient, but this is not just fans' expectations. Kakko was the most popular pick for the Calder last year. Lafrenierre this year. From most every hockey publication. Kravtsov was at one point ranked the #1 prospect in hockey before he came to NA. And even if Lias was never a high-ceiling pick, the common take was that he had a high floor, was a pretty sure thing NHLer at the least.