JJ: “Yanks Gotta Learn to Say ‘When'”

New York, New York

By John Jastremski

sports@queensledger.com

The Yankees organization is always a group that is going to be put under the microscope because of the team, the brand and the tradition of the organization.

I do think it’s important to realize that despite the amount of money that they spend, it’s incredibly impressive to have a streak of over 30 plus years without a losing season.

Especially when you consider what has happened with the Mets in both 2023 and this season with enormous payrolls, the achievement of the Yankees consistency becomes even more impressive.

However, they aren’t perfect. In fact there’s plenty of stuff to critique because in Yankees land not having a championship in almost 20 years is also hard to comprehend because of the history, brand and everything that comes with the franchise.

One of my biggest critiques that I currently have with the current management group would be an unwillingness to make a mistake when it comes to a player evaluation.

There are countless examples of the Yankees giving a young player entirely too much leash at the big league level without the results.

Do the names Greg Bird, Clint Frazier and Miguel Andujar ring a bell?

That unwillingness has been on full display for a good chunk of the 2026 season when it comes to the shortstop position.

The Yankees are simply unable to quit Anthony Volpe.

For the better part of the last year and a half, it’s been obvious to anyone who has a pulse.

The Yankees are a better team when Jose Caballero is the shortstop.

Case closed.

Yes, due to injuries throughout the course of this 2026 season, the Yankees have been in a position where both Caballero and Volpe have found themselves in the everyday lineup.

That time has officially come to a close.

Trent Grisham is back. Ryan McMahon is back. It is much easier now to write a more consistent every day lineup without the constant moving and shaking of positions and players.

The Yankees have a very simple decision moving forward.

Play Jose Caballero everyday at shortstop.

He’s been the more productive hitter. He’s been the more confident fielder. Oh and here’s another simple fact.

The Yankees win a lot more games when he plays the position.

The Yankees are 14 games over .500 with Jose Caballero at shortstop. That is not a coincidence.

It’s also not a coincidence that entering Monday, the Yankees biggest game of the season to date against the Tampa Bay Rays, Caballero was starting at the spot he should be at every day.

The Yankees wanted to be right on Anthony Volpe.

He was a big prospect, it was a great story. Local kid grew up rooting for Derek Jeter, ending up in pinstripes.

Cute, but ineffective.

The Yankees have a better option, don’t let pride get in the way.

You can listen to my podcast New York, New York every Sunday & Thursday on Spotify, Apple & YouTube. You can check out NY Sports Rush with Sal Licata every Monday,  Wednesday & Friday on the Bet Rivers Network. You can watch me nightly on Honda Sports Nite following Mets postgame on SNY.

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