Their draft and development has been solid, but I think he fell way too quickly in line with the old "your veterans get the money" & "veteran depth is important" lines of thought that we've been talking about here for a couple of years now just being wrong. He was spending a pile of money on Kulikov and Myers instead of throwing the bag at Trouba to keep him happy and maybe extend their window. Threw a bag of money at players on the wrong sides of their primes (that are good players and all, but still).
He hasn't done a bad job necessarily (though losing Trouba for what they did is fringe criminal) but he hasn't done a particularly good job either. They were a team in need of some bold moves a couple of years ago, to either trade some of their veteran players for youth that would line up with their core of kids, or trade some of the core kids for impact veterans to try to win now. They basically have two distinct core groups on the team, neither good enough to win anything on their own and an overlapping window together that was always going to be at best 2-3 years long. This was a known structural problem with the way their roster was constructed and they did nothing to fix it.