His results as a GM:
The Team is averaging about 97 or 98 wins a year the last few years, so that's terrific.
They never fall off a cliff. The clubhouse / team always seems playing like a team; very little drama.
They also developed the best position player in the league in Judge, and other talent as well.
Holmes, until the very end of the season, looked like a super acquisition.
The playoffs are a crapshoot, and unfortunately the Astros have been a thorn in their side.
The Stanton contract is a little aggravating to me;
The Cole signing is sometimes fine, other times disappointing.
(It's hard to forget he was Cy Young #9 voting this year, which is great...but he is being paid to be Cy Young #1, 2 or #3)
Cole's ERA+ was only 111 this year... so advanced math says he's a bit above average.
(Holmes ERA+ is 154; King was awesome at 171; and Cortes was 163, as comparative #s)
Other pricier starters they've signed or traded for haven't panned out either.
There are reasons for people to grumble. There are reasons to be fine with Cashman re-uppping.
Maybe it's one of those be careful what you wish-for type of things.
I guess it all comes down to wins, his teams keep on wining around 95-100 games a year; so he stays, even though many are not thrilled win the play-off outcomes.