Kyle is one of the nicest guys in sports, at least from the outside looking in.
Can't let him being a tremendous person blind to the fact his team has won zero playoff rounds and created what seems to be a soft passionless group on the verge of another first round failure, but I'll give him the benefit of the doubt on that.
Love his creativity and ability to find guys like Kase and Bunting. Those are the types that help you win when it matters, although Kase's body is not fit for the long haul. Don't recall a player who seemed as fragile.
Hate him trapping himself when it comes to money where he has to pay resources to get out from under bad moves IE: Ritchie But, love that he didn't just pretend things were okay with Slick Nick and sent him away. Always nice when a GM acknowledges a mistake, and that it was, and a costly one. Nice that he didn't just have to Marleau this one and got back an asset who appears to be a serviceable Dman in Lyubushkin.
Don't like his penchant for finding washed guys like Thornton, Simmonds, Spezza, etc. and consider that fixing the toughness/grit/maturity issue.
Hated the naming of JT as "C". A guy who was brought in via FA becomes the appointed leader as an outsider instead of promoting from within, if you will. Perhaps, Matthews was the pick but his Arizona summer troubles nixed that, I don't know, but JT should've never been named captain. I think that set this team back.
Hate his willingness or need to burn picks. A GM who does this as routinely as Kyle better get results. He has not to this point.
Love his care and compassion for injured players. The injury to Cobra in NJ really stands out to me.
Hate his philosophizing and self-validation of paying 4 forwards 40 million when it has failed over and over. Think he's brutal at doing long term deals with players giving wrong terms and bloated cap numbers.
Love his belief in what he's doing, as misguided as I think his approach has been. He has tweaked his philosophy while not abandoning it. I appreciate his willingness to try new things when he fails.
Wish he prioritized intangibles more than he does. He is a cold sterile analytical type. There is value there but hockey like all sports is a human game. I wish he'd paid more attention to that from the beginning. Don't believe the player-friendly culture is conducive to on-ice success but is a draw for FAs. Many guys want to come here to be passengers at ends of careers. He encourages that.
Not a fan of the very child-like ways he deals with his players when speaking of them in the media as to handling them as if they're extremely mentally brittle. I would swear he's managing peewees when he speaks sometimes. Would prefer he was bolder as to being about winning and not put so much focus on things that don't have to do with that.
Not a fan of his addiction to Soo connections. Every GM has their guys but he seems to pump a lot of water from that old well.
I know I was deathly curious when he took over if his philosophies would translate to winning. I think he found they don't and as mentioned above has at least been willing to tweak them somewhat.
Applaud him for moving on from Babcock and bringing in the guy he thinks represents his philosophy on and off the ice.
Wish he'd tweak his philosophy on paying 4 forwards 40 million and ship one out. He doesn't seem to have the stones to do that tough thing that needs to be done. He'd rather grind away on the periphery than get to the net so to speak and realize too much cap is in 4 guys and as much as you love your players, that model is just not a good one for winning Cups.
Overall, I love the guy, personally. He's a great representative from a PR standpoint. I wish he was equal in pushing hard to win it all and came off that way through more accountability. I don't believe he runs a tight ship as to promoting a sold out for winning culture and should be managing younger players and not men.