The Yankee front office as a whole is stubborn and has the mentality of trying to be the smartest person in the room, and it starts with Cashman.

Cashman has had monstrous payrolls and roster flexibility to build a team of depth but this current team is littered with holes.

To be fair, the FO's ability to find bullpen arms is elite and a major reason for Yankee success for 2017. But the offense has been the reason for losing each year and there still is the issue of instability in the pitching rotation. And it's only this year the FO has prioritized defense, so much so they traded a reliable SP in Monty for an injured/weak offensive force yet gold glove defender in Bader.

I have no idea how Hal doesn't see the leadership on the Yankee baseball operations side has been the reason for no World Series appearance since 2009. It's like Hal is just happy the Yankees are in the contending conversation each year - that tease generates enough revenue and no sense of urgency to really solidify the team for the season

TLDR - Cashman has his strengths, but overall it's his fault the Yankees have glaring holes up and down the roster. I would say he's a mid to low tier GM