He’s given Hal every reason imaginable to justify firing him over the last 6-7 years and especially ever since Steinbrenner died 14 years ago. No GM in any sport wastes as much money and young players as he does in bad contracts, an inability to develop young players thus requiring huge contracts to free agents in order to compete (they haven’t developed a single home grown pitcher into a star since Andy Pettitte and Judge is the only position player since Jeter), his always betting heavy on washed up and/or injury prone vets all staying healthy and having career years at the same time, and how he seems to think anyone can play any position and how it’s perfectly fine to ignore positions of need for years on end. It’s why we’re all so fed up that the team is shocked that a bullpen entirely comprised of castoffs and an infield with two 34-35 year olds who are injury prone and have been in decline for years, that had no third baseman on the roster, that also won’t commit to its top catching prospect as the primary starter, and had no backup plan for Stanton getting hurt (he missed 140+ games in 2019, 20+ in 2021, 52 in 2022, and 61 last year) might run into trouble.
He’s also created the toxic culture of no accountability that’s the team’s biggest problem. The lack of accountability leads to bad situational baseball, countless mental errors, and no top down leadership since the coaching staff are just puppets which is why the team always folds at the first sign of adversity. That’s as bad as the lack of depth and the injury prone roster.
I get that Hal doesn’t want to be his dad during guys 2-3 weeks into the season and regularly firing guys after 1-3 years, but Cashman should’ve been gone after 2004. He’s botched 3 separate championship windows in a 20 year span. How many general managers can say they’ve done that? A good GM with his resources should have won at least 4 titles from 2004-2023 and he’s got 1. It’s long overdue.