Brian Cashman
Kim Klement | USA TODAY Sports

The Winter Meetings are, in a nutshell, Major League Baseball’s version of Comic-Con.

It’s actually uncanny how similar the two are. Both take place in sunny San Diego at a hotel/convention center with way more space than should be allowed. Each event is a yearly who’s-who of their respective industries and mediums. The Winter Meetings are all about juicy free agent signings and trades, and what the new baseball season may bring. Comic-Con is a celebration of pop culture full of anticipation over the latest hit franchise’s sequel coming out in the next year.

Speaking of sequels, this year’s Winter Meetings very much fit that mold for the Yankees. It was there in San Diego, almost exactly three years ago, where general manager Brian Cashman closed the deal and got his man. A failed draft signing and a few missed trades later, Gerrit Cole signed with the Yankees in free agency.

Now, as 2022 reaches the finish line, Cashman heads to San Diego with an even greater task: Re-sign star outfielder Aaron Judge.

Everyone remembers the anticipation back in 2019. The Yankees had just lost to the Astros in the ALCS and could now poach Houston’s best pitcher. Nine years, $324 million, and an expensive bottle of wine later, Cole donned the pinstripes.

Fast forward to today and, as Aerosmith once said, it’s the same old song and dance. Ken Rosenthal of The Athletic reports Judge will likely sign a nine-year deal. The only question is if it will be with the Yankees or his childhood favorite Giants.

A successful sequel builds on the original storyline. In this case, it was the Yankees knowing Cole was born to play in the Bronx and making it a reality. It’s the reverse this time around. The Giants aren’t just doing due diligence like the Dodgers did with Cole in 2019. They seem very serious about bringing Aaron Judge west.

Cashman simply cannot let that happen, even if the Bryan Reynolds siren is tempting. Judge is the reigning MVP and set a new American League record with 62 home runs in a Yankees uniform. Is Hal Steinbrenner really going to draw a hard line at eight years, $300 million? Presumably not, since ESPN’s Jeff Passan says that offer could increase.

This is the part where Cashman listens to “Eye of the Tiger” over breakfast and hits the ground running in San Diego. Criticize him all you want over his analytics obsession. He’s still probably one of the smartest executives in baseball. Cashman knows how to build winning Yankees teams and how important Judge is to the future of them. This means he also knows, as we’ve discussed ourselves, the Giants need more than Judge to leapfrog the Dodgers.

Cashman knows this much. If he pushes Hal Steinbrenner enough, the laconic and reluctant Yankees owner will hand over the checkbook for Judge. The Giants barely spend as it is, and we’re supposed to think the Yankees are intimidated?

Not this time or ever. Judge didn’t turn down the Giants to attend college, but their cross-bay rival Athletics. He then blossomed into being a Yankee so much that the captaincy seems a practical birthright. That isn’t to say the Giants’ interest isn’t legitimate, but adding him seems more of a boost while continuing to build.

New York, meanwhile, just won the AL East and is ready to run it back. Could they without Judge next year? Probably, but it just wouldn’t be the same. The man isn’t just a good player on the Yankees, he is the Yankees, and the infinite No. 99 jerseys in the stands prove it.

Cashman, you’ve been down this road before and know it well. Go get your man.

Josh Benjamin has been a staff writer at ESNY since 2018. He has had opinions about everything, especially the Yankees and Knicks. He co-hosts the “Bleacher Creatures” podcast and is always looking for new pieces of sports history to uncover, usually with a Yankee Tavern chicken parm sub in hand.