Considering the circumstances of his hire and what he was given, it's been pretty good. We also do not know what directive he was given by Dolan. Clearly he wanted something different from what Gorton was providing, whether that was on the physical side of things (remember this was post-Wilson) or the standings wise.
I'm more concerned with his coaching choices than his personnel choices. Gallant was jettisoned from Vegas after making a Cup Final with him. Laviolette has a similar track record, but again if Dolan is asking for them to contend, are you going to go with rookie coaches?
His two big f*** ups are Buchnevich and Eichel, with the latter being something that could still be debated at the time of the trade. The Buch deal was horrendous the moment it was official. Eichel was a risk and Mika was a very good player still.
Regarding Goodrow, everyone was saying either a buyout or trade by year 3 or 4 and it went exactly like that. The contract was basically structured that way. Is it his fault his 8M 2nd pairing RD turned into mush? Lindgren also fell off a cliff at a much earlier age than we expected, even if we knew it was going to happen. Gorton traded and signed Trouba and he retained Kreider at the 2020 deadline. Then you had the DeAngelo contract which had to be bought out.
Drury's biggest moves have been Trocheck, Miller, and the Mika/Laf/Igor extensions. I'd say the jury is still out on each of these moves, although Trocheck has been good since he was brought in to be a 2C and has exceeded those expectations.