Sometimes you can see some GMs that just had some bad luck, they had contending teams, went for it, couldn't get over the hump and then the team started going downhill. That's at least understandable.
And then you have Kekalainen, who has just been matter of fact terrible at his job. Whether it was trading for pending UFA Duchene and losing Panarin & Bobrovsky for nothing while being an eight or seventh seed (I can't remember) that lost in the second round,or it was giving Erik Gudbransson a 4 x $4M contract when nobody wanted him (as evidence of him being on 6 different teams in 4 seasons), trading Josh Anderson for what amounted to basically nothing, hiring Mike Babcock only to fire him two months later, mostly unimpressive drafting, etc. He's a guy that was a really good European scout and the scouting was never all that good in Columbus. Red flag.
For the Duchene/Panarin/Bobrovsky fiasco, I can't help but think that was ownership telling him to dive head first and try to win. No sane hockey mind would have done it, but still, that was 6 years after he got the job and the team had been going nowhere.
To his credit, though, trading Seth Jones to Chicago was a very shrewd move. However, that cap space saved has been pointless, and all those draft picks they acquired have turned up a less than reasonable outcome, David Jiricek TBD, and Jiricek is apparently fed up.
Being an NHL GM must be fucking fun, man. You're almost guaranteed two contracts, even if you're not good at your job.