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Brian Cashman has quarter-century relationship with the Steinbrenners and is treated like a family member.

In the end, Cashman is just serviceable enough. Just serviceable enough to maintain a competitive roster from anywhere between $190-$255 million. But that’s the problem. It’s never competitive enough. Cashman cannot do more with less. He frequently does less with more.

Two things can be true: Hal Steinbrenner is holding the Yankees back because of his unwillingness to spend more, and Brian Cashman isn’t a good enough GM to work around those restraints because many other GMs operate well under New York’s payroll threshold and have seen far more success.

Cashman effectively serves as Steinbrenner’s shield, churning out quality teams while adhering to the financial limitations set by the owner. The Yankees retreated below the luxury-tax threshold in 2018 and 2021 to reset their penalty rate to the minimum. During the labor negotiations, Steinbrenner supported a lower threshold and stiffer penalties that would have diminished his team’s ability to outspend other clubs.

After pretty much knowing the Steinbrenners have him in their back pocket to go through with their cheapskate ways? The comfort knowing Cashman will likely never oversee an unmitigated disaster of season (he might, though!) is enough for Hal.

Cashman will be in the Bronx and running the front office until he decides his time is up. It’s a sad reality Yankees fans have to get used to. Many seem to believe a historic 15.5-game choke job might do him in. It won’t.

https://yanksgoyard.com/2022/09/07/yankees-brian-cashman-job-safe-for-life-hal-steinbrenner/

Don't tell Derek Jeter the 'World Series or bust' mentality a thing of the past.

If the team is a contender, quasi-contender, hanging around a Wild Card spot, it’s all just fine for Hal and the Yankees. Remember Cashman’s comments on the “World Series or bust mentality being a thing of the past”? That’s the vision executed perfectly. It pretty much translates to: “We’ll be as good as we’ll be, we guess. And probably won’t be aggressive enough to change something that’s not working out. We’re the Yankees. That’s all we need to be: our brand.”

https://www.sportingnews.com/us/mlb/news/brian-cashman-yankees-contract-mlb-postseason-general-manager-joe-girardi-rebuild/f898w8cunfhp1tdel5hc9ub1g