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

Just because the New York Yankees‘ impending free agency class isn’t supermassive, and just because the luxury tax mandate is off — it’s off, right? — doesn’t mean they’re done with difficult decisions.

Theoretically — theoretically — Brian Cashman should be chasing a certified shortstop and center fielder to help make Gerrit Cole’s prime a more enjoyable experience. He also might consider dangling Luke Voit, who he hates for some reason, and Gio Urshela for rotation help.

Lots of moving parts are sure to shift past each other this offseason, whether New York jumps in the deep end of the pool for Corey Seager, or keeps things lighter while waiting for Anthony Volpe to hit the bigs.

Don’t let the free agency bill distract you from the people already in this locker room who need to be locked down or let go, though.

For the purposes of our experiment, we’re treating the team’s upcoming free agents (minus one!) with a degree of skepticism about their possible returns. Most departing Yankees feel like either locks to leave or locks to decide on their own time, independent of the team’s braintrust.

Andrew Heaney isn’t coming back. Joely Rodriguez more than likely isn’t coming back. Darren O’Day is unfortunately on the verge of retirement. Corey Kluber? If someone else wants to pay him $10 million again, he’ll bolt for greener pastures. Brett Gardner? Again … that’s his decision to make. After his second half, we don’t see this unfolding any other way than an exact copy of what we all just went through in 2020-21.

This crop, in a word, stinks. Snoozer. So what better time than the present to make some difficult decisions about your roster, when there aren’t really any core players hitting the market?

Again … except one, depending on your definition of a core. The next few weeks could go a long way in determining that. Only partially kidding.

The Yankees might have to make these 3 tough contract decisions this offseason.

3. Anthony Rizzo Worth a Fat-Esque Extension?

A new contract for Anthony Rizzo seemed a lot less “essential” when Luke Voit was slugging during his COVID absence, right?

When Rizzo arrived, we thought the Yankees could juggle both men. Of course they could! But when the Gold Glove deadline import returned from his absence, it became clear that even though they could, they had no intention of doing so.

And so, Voit is out of our future plans, as far as the current scope of things is concerned. When you look at it that way, a three-year deal for Rizzo certainly feels preferable to … hoping DJ LeMahieu is alright at first base, as he hits .268 with eight homers.

Outside of a Matt Olson trade (drool), there’s no preferable outcome to paying Rizzo for a few more years. Locking him and his exceptional defense in from age 32 to 34 doesn’t seem like a terribly difficult call. He’s already done several things these past few weeks we haven’t seen from a Yankees first baseman in ages, from scoops to 115+ MPH liners into the gap to going with an outside changeup for a bloop single. He walks. He fields. He’s been decent-to-good with the bat.

As long as he’s having fun (remember those rumors?), he seems like someone the Yankees should retain. We’ll find out if they agree sometime in December. Riz is the only free agent worth considering.

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.