Yankees repeated mistakes with Aaron Judge that they made with Derek Jeter during negotiations

When negotiating with Aaron Judge, the Yankees organization has not learned from the mistakes it made with Derek Jeter.

We might not be that far away from finding out if the New York Yankees botched their entire future, losing generational talent, Aaron Judge, to free agency.

If they do, one of the big mistakes to blame is the fact that the organization — and Brian Cashman, specifically — upset Judge by breaking his trust and going public with details on the negotiation.

Cashman told the media straight-up what the Yankees offered Judge — $213.5 million for seven years — which reportedly upset the record-holding slugger. The offer was made public after the organization and Judge failed to come to an agreement on an extension before the 2022 season began.

What followed? Oh, just a historic, 62-home run season from Judge that proved he was probably worth whatever money he wanted. A blank check is what they should have offered him.

What’s even more frustrating is that the Yankees have made this unprofessional mistake with a star player before, too.

Yankees broke Derek Jeter’s trust. Now they broke Aaron Judge’s. Will it bite?

The Yankees made this exact mistake with The Captain himself, Derek Jeter. Like, to a T.

On an episode of Drink Champs, Jeter had this to say:

"“…told my agent if any other team calls, tell them I’m not interested. Treat me fairly. Treat me fairly. Don’t make it pubic, only thing I ask. And then [the front office] made it public.”"

This in mind, you would think the Yankees might have learned and wouldn’t repeat it. It’s borderline unprofessional to take a hard contract number public because it completely pulls any leverage the player has. The rest of the market knows exactly what the starting number is, which anchors the price in at a certain point.

At least, that’s the strategy in practice. In reality, Judge outplayed even the highest of estimations in 2022, and that $213.5 million is probably going to be smashed through.

We know how it worked out with Jeter. He played out his entire career with the New York Yankees. Maybe that’s why they repeated this mistake? They never had to face the consequences. Perhaps this time things will be different.

Judge will have suitors everywhere. The San Francisco Giants are closer to his hometown and could offer him the best number.

Jeter was adamant throughout the process that he never wanted to leave New York. He even went so far as to say he didn’t know if any team ever even inquired about him as a free agent because he didn’t want to know. Judge’s allegiance may not be so strong. We’ll find out soon.

Though he seems to genuinely love the fans, you have to wonder if maybe Judge is done with the front office.