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Brian Cashman’s leadership abilities have to be questioned

The Yankees’ GM is projecting a leadership quality that typically ends in failure.

New York Yankees GM on phone during spring training Photo by Thomas A. Ferrara/Newsday RM via Getty Images

“Consistent successful operation” — BC

Brian Cashman has lost his way.

His flat-out embarrassing comments this past week show a man who bit his tongue at the end of the season to save face — but the second the dust settled, he came out swinging. He provided comments stating that everyone else is wrong and he is right. It was a similar tone to what Cashman has expressed over the past couple of seasons, but this conversation had a heightened energy (anger) level. John pointed out this week how similar the comments were to another recent New York GM.

It is easy to assume that entitlement is the main driver behind these comments, but I think Cashman has moved into a new realm of emotions: insecurity.

“We were not in a losing situation this year but we lost enough to not make the postseason” — BC

I once thought of Brian Cashman as the ultimate entitled leader. His tenure with the Yankees has seen the highest of highs. He has forged a close personal relationship with the owner and won championships 14 years ago — the combination somehow providing him with ultimate job security and an inflated sense of entitlement.

We have all been around this type of person in life. Maybe it’s a co-worker. Someone who thinks they deserve everything, including the protection of never being challenged. If you let these types of individuals blossom, gain power, and continue their privileged ways, that sense of ego will only grow.

But what happens when an individual like that slips up or begins to receive criticism? Well, that entitlement begins to morph into insecurity. Brian Cashman’s comments are showing cracks in a man who has been told he is the greatest and can do no wrong his whole career. His comments this week hint at the fact that he reads everything that is said about him in the media. You’re the GM of the Yankees — should you be concerned with media comments to the point where you go on an expletive-filled rant? That sounds more like a man unsure about himself rather than a stable leader.

“Why do I have to say what mistakes I’ve made recently?” — BC

Insecurities among people in leadership positions are not inherently bad. It can, in some cases, keep you grounded and open to advice when paired with proper leadership skills. Good leaders can admit mistakes and do not feel the need to dance around them.

But when insecurities become the main driver for how you lead and make decisions, then it is likely the beginning of the end for you in that position. Oftentimes in leadership, insecurity can make leaders more rigid and stuck in their ways — hoping to appear in control when challenged about their performance — thinking it will persuade people to believe in them more. It never works out that way.

I know the counterargument could be ‘Well isn’t that just entitlement’. And the lines can be blurred, but the difference in this situation is that for the first time in a long time, I think there is a true sense of threat to Brian Cashman.

“Good leaders separate what is real and what is not real” — BC

It took Cashman only a few months after the season to go full heel — when his boss merely a few hours earlier was preaching a different tone about failure and big changes. The comments by Cashman felt childish and off-brand for the Yankees.

What makes a good leader is separating what is relevant and not relevant, filtering out the noise, and staying poised. Cashman expressed in one media session that he was unable to do any of those. He stated multiple times in different forms that words mean nothing but continued to talk as if we were supposed to believe in anything he was saying. His words are powerless because he defends every story and every angle. And if you defend everything then you defend nothing. This screams insecurity to me.

Cashman was asked to be introspective after a failed season, but it is clear that the mental aspect of his leadership abilities is faltering. If Cashman continues to project his insecurities to the media, then it is only a matter of time before he does it behind closed doors with his staff (if he hasn’t already). Two things happen in that scenario: the workers leave, or he gets fired.

We still know the job security that Steinbrenner provides, but I’m sure he is not thrilled about the way that Cashman handled himself. Was it a moment of weakness or a true sign of a GM who is nearing the end? The 2024 season will tell a lot.