He hasn't done nothing since getting close a few years ago. I genuinely believe he has been trying to go the trade route to improve the team, players just instantly have Buffalo on their no trade list or they might be FA's in a year and wouldn't talk extension. I think of last off-season when there were apparently packages accepted for Ehlers and Necas. Ehlers said he wasn't signing an extension with anyone and Necas flat out said, no.
The goaltending plan really blew up when Ullmark bailed. We are still feeling that today. There was no plan if Ullmark left which really makes me think Ullmark led them on, who knows but I remember something along the lines of 5 years 25 million being his give me and I'll sign and then he was down to us and Boston and took less money to leave.
Then it pivoted to youth because goaltending is incredibly hard to come by with a contract that isn't an anchor. UPL showed ok, then stumbled and Levi came in fresh and looked good and then UPL took over while Devon floundered. Comrie was bad. He then properly put Devon down for good, a bit late, this year.
Tldr - I believe he is trying, solid rumors out there indicate it but him banking on Ullmark really set his plan back awhile.