MLB Insider Suggests Boone And Cashman’s Jobs On The Line This Season

Longtime baseball observer Ken Rosenthal dropped a bombshell on the Sunday episode of Fair Territory: if the Yankees fail to make the playoffs, both Aaron Boone and Brian Cashman could be out. 

“This is a team that lacks fundamental soundness… at times looks like it doesn’t know how to play baseball,” Rosenthal said. “Now, things can get better… when Judge returns to the outfield… or if Max Fried stays sharp. But more likely, they could get knocked out early. Does Aaron Boone come back? Does Brian Cashman come back, or do they finally turn the page?”

That’s a seismic claim that doesn’t seem to fit with Yankees owner Hal Steinbrenner’s history.  

Not only is Boone fresh off a two-year extension signed in February, keeping him through 2027, but he also led the Yankees to the World Series in 2024, their first appearance since 2009. Rosenthal’s question now cuts to the bone: is yesterday’s success enough to save today’s regime?

Despite a 97% implied probability of reaching the postseason, per BetMGM reporting, the Yankees persistently underwhelm against top-tier teams, and their bullpen remains a weak link. Their recent stretch includes lopsided losses and defensive blunders that feed frustration even amid October talk.

Still, their schedule softens from here on out. 

Twenty of their final 32 games are against low-performing teams like the White Sox, Nationals, Twins. It’s a prime opportunity to bolster their record and secure a postseason berth. If they go 16–4 or better across that stretch, they could reach 86–91 wins, likely enough to clinch a spot.

It also does not take into account that this is a Yankees team that is playing without Gerit Cole this season, lost Clarke Schmidt, have had a very limited Giancarlo Stanton and is now facing a limiting injury to Aaron Judge.

Rosenthal sees a do-or-die finish that could cost Boone and Cashman their jobs. The Yankees’ fate now hinges on consistency and the outcomes of those next few weeks. It’s a bold question and one that even Rosenthal admits he doesn’t have an answer for.