Yankees: 3 difficult contract decisions NYY will have to make this offseason

1. Is This the Year for the Aaron Judge Extension?

If not during the offseason without a self-imposed salary cap, when?!

Even the bitterest among us seem to agree, at this point, that the New York Freaking Yankees, the richest organization in sports, should not simply allow Aaron Judge to walk out the door. Nor should they trade him for an “Alex Verdugo type” — of course, that’s an outfielder with preexisting criminal complaints that we all choose to ignore who can do a reasonable facsimile of a B+ job every month or so.

Theoretically, a burn-and-churn player development machine like the Rays could trade Judge after he just proved his ability to stay on the field for nearly a full season, which was the last thing many fans needed to see before they could full-throatedly endorse an extension. But where’s the fun in that if you’re the Yankees? It almost assuredly means “bragging about a downgrade.” Some fans might prefer rooting for laundry to rooting for an elite player, but if the Yankees’ plan is to operate like the YANKEES, there’s no reason to ditch talent like this.

In 2021, Judge is playing on a one-year, $10.18 million arbitration salary. That will rise next year in his final season before free agency to quite a high level — not quite Betts High, but between $15-20 million, most likely.

Wait — sorry, did you say “final season before free agency”? Oh, the Yankees should unequivocally act now, as soon as the new CBA is signed, which should clear up a few of the particulars.

Hopefully, they agree. Like it or not, this will be a pivotal offseason for Judge’s tenure in the Bronx.

Yankees: Top free agency priorities for Brian Cashman after 2021 season

The New York Yankees can become a dominant team again with a few strategic acquisitions during the upcoming rich free-agent market.