Brian Cashman’s Aaron Judge updates show how big of a mistake Yankees’ extension was

The day after the Winter Meetings began, the New York Yankees, clueless as always, announced a contract extension for general manager Brian Cashman. It was something fans always knew was coming … but yet again the timing couldn’t be more disheartening.

Yankees fans are waiting for any news on Aaron Judge, or perhaps other free agent/trade targets for that matter. The time for that to happen was this Sunday-Wednesday, during the Winter Meetings — the most active string of days in any given offseason.

So when the Yankees Twitter account announces something in that timeframe, fans are expecting some sort of momentous move to change the complexion of the roster. Instead, we got Cashman, which took all of the air out of the Free Agency Balloon, which already had a small hole in it.

Secondly, on what planet are the Yankees extending Cashman without an assurance that Judge returns? Or without a plan/moves in place to address the 2023 roster, which is, at worst, awful without Judge and, at best, not a surefire contender with him?

Maybe that’s wishful thinking because it’s doubtful the Yankees would’ve ever strung Cashman along like that, but this team has won one World Series since 2001 and has appeared in just two since 2003. Cashman’s been the GM since 1998. It’s now as clear as ever the Yankees are fine with “contending” … but not too ferociously.

It gets worse, though. Cash popped up at the Winter Meetings in San Diego and said ALL the wrong stuff out loud. All of it. He’s continuing to alienate Judge, as he did last offseason when he revealed the team’s offer to him.

Brian Cashman appearing on TV during the Winter Meetings was a disaster for Yankees

Cashman said he had no idea Judge was planning to arrive in San Diego on Tuesday, further confirming the Yankees might be on the outside looking in here. Why would he even admit that, even if it was the truth?

That’s not all, though! Cashman also said the Yankees don’t know if they’ll get a chance to match the last and best offer presented to Judge. Again, why are you admitting this other than to a) look stupid or b) give Judge more of a reason to leave the second he gets an offer that beats the Yankees’ best?

Speaking of offers, last week it was reported the Yankees presented Judge with an eight-year, $300 million deal. But apparently that wasn’t all, for whatever reason.

Cashman said the Yankees have made “a number of offers” to the reigning AL MVP since free agency began. We have to ask “why?” one last time. There are, at most, two offers for Aaron Judge. The first is a long-term contract that exceeds $300 million, one the Yankees feel comfortable opening the negotiating with. The second, if necessary, is an offer that exceeds whatever he was given from another team.

Why are the Yankees making this more difficult than it needs to be? Why are they embarrassing themselves even more when there’s already to be plenty embarrassed about?

And what’s the backup plan? Don’t ask Cashman. Don’t ask the guy who just extended himself.

NO idea.

Just like hours before Opening Day when Cashman and the Yankees had to tell the world Judge rejected their seven-year, $213.5 million extension, this public appearance from the GM might foreshadow nothing but disappointment.

If it does, it’ll be a long, long four years of limping back to relevancy.

Yankees announce 4-year Brian Cashman deal, get ratioed spectacularly

The New York Yankees have heard your cries for Aaron Judge, and used this exact moment to announce Brian Cashman would be around for 4 years.