Excusing the fact that most reasonable people knew the world was headed for a shutdown so COVID should not have surprised him, Green looked done in the games he did play, and Holland was in the best position to know what he was (not) getting as his former GM. It was "only" a pick, but it just contributes to the death by a thousand cuts that Holland has doled out since he's been here.
But Holland apparently wasn't bright enough to know what AA's flaws were after, again, being the GM when he played for Detroit. Not only that, but Ken was the one who had to deal with his contract grubbery the first time. Why did he think it would be any easier a second time? Along with the goalie waiver debacle, it paints a picture of someone who doesn't learn from their mistakes- probably the worst trait any executive could have.
I wish I was only looking for a move in net for "excitement" purposes. In reality, it's the most important position on the team. Looking at his tenure to date, Holland has had nearly two years since he was brought on to realize the goaltending is an issue and subsequently fix it. I can understand not being able to navigate the market for an immediate solution in Year 1, but this last off-season? Absolutely zero excuse. He needed to make a move- either by paying to move a contract so Markstrom would fit, not signing the depth pieces he did, or finding a salary in/out trade. He doesn't get a pass here. It was or should've been his main priority and he failed to address it.
...and then he did it again with Grosenick. Again, that's the fireable part to me- he didn't learn from the first time. That's a fatal flaw in any executive in any industry.
But ultimately "player depth" doesn't matter when you start almost every game down 1-0. I also can't give him a pass on cap space because ultimately he chose to sign Kassian to the extension he did, which is already handicapping us. Holland has done very little to move this team forward, and outside of a dead cat bounce last year (that even Chiarelli accomplished) we're back to what we were pre-Holland: a glaringly flawed team with obvious needs that the GM doesn't have the wiles to fix and the coach is too stubborn to get much more from. Something has to give here.