Holland loved distressed scouting grounds, likely the result of embracing Sweden and Russia in a heavy way when people were apprehensive, but you could see them go to areas that were being ignored. I think that worked out well for him and the Wings in a lot of his early director of amateur days and was how he rose to GM. I think he was slow to evolve to some of the online hockey tools, people weren't avoiding the Czech Republic when we seemed to be taking advantage of it, they were in a down phase with some of their talent.
He also got bled of a lot of organizational talent. It has been a while since Ken Holland was involved with this team, I thank him for 25 wonderful years, 4 cups and 6 finals appearances. He played a massive role in producing a quarter century of having arguably the best team in the league. It didn't end well, we know through Devellano that they told the Ilitch family to blow it up after the Boston series loss. That wasn't ownerships desire, his tendency to lock guys up long-term both in the non-cap era and then early cap era caused major maneuverability issues. I actually remember thinking Joe MacDonald wasn't doing a great job but that certainly changed with Nill in Dallas so that was a very wrong take. Absent assured top picks he was trying to build a big physical team for playoffs but didn't get the right pieces for that. Hard to do where they were picking but certainly a rough bunch of years in the 2010s.
I get him moving on but I do actually really wish he was in an advisory role as was originally announced. I get him leaving but I think he would have been a useful sounding board to Yzerman. Holland always saw the game a little different and I think that instinct helped him a lot on the balance of his career. It helped him in his early scouting days, it helped him zig and zag at times approprietly, but he missed the second rebuild on the fly which was always going to be a daunting task. He tried a lot of the same principals but wasn't getting a bunch of the lucky breaks. There isn't a team that wins without some luck and it certainly smiled on him for a lot of years, but towards the end of his tenure we had too many competing ideas and I don't think we followed through on a lot of things and it increased the tailspin.
Like with the Dumars descent though I will remain removed from the crowd that loves to criticize Holland in Detroit. On the balance he is one of the best things that ever happened in this franchise, I really hope some people at some point can accept the balance of his resume instead of the end at some point.