Aaron Judge Yankees
Tim Heitman | USA TODAY Sports

The inevitable happened last night when Aaron Judge not only won his first American League MVP trophy, but he also discussed his free agency.

It wasn’t long before that Yankees general manager Brian Cashman confirmed the team has indeed made an offer to Judge. Yet, the big slugger seems determined to take his time and enjoy his free agency. In fact, it might be a while before he makes his decision.

“It’s still pretty early and a lot of stuff doesn’t start kicking up until the Winter Meetings in December,” Judge said. “But it’s going to be a fun process that my family and I will definitely enjoy.”

Everyone knows MLB’s Winter Meetings, set to take place Dec. 4-7 in San Diego this year. Fans will recall it was also shortly after the Winter Meetings in San Diego in 2019 that the Yankees inked ace Gerrit Cole to a nine-year deal. Similarly, after the meetings occurred in Las Vegas in 2008, Cashman famously convinced California native CC Sabathia to sign with New York.

One way or another, Judge’s willingness to wait only helps the Yankees. Even with the Dodgers and Giants looming with supposed offers of their own, New York is still the team that knows Judge best. Every professional accomplishment from his 2017 AL Rookie of the Year award to his MVP trophy happened in pinstripes.

Consider this. On top of mentioning the Winter Meetings, Judge implied his decision wouldn’t fully come down to money, but winning.

“For me, I want to win,” Judge said with his signature Jeterian stoicism. “I’ve come pretty close with the Yankees. My ultimate, most important thing is I want to be on a team with a winning culture and a commitment to winning. First and foremost, it’s a winning culture and a winning future.”

Again, advantage Yankees. Say what you want about Cashman’s analytics addiction and how he builds teams. The fact of the matter is that save for 2013 and ’14, his Yankees are always very much in the playoff picture. They won 99 games in 2022 despite playing sub-.500 ball after the All-Star Break.

If there’s anyone who can understand and relate to Judge’s desire to win, it’s Cashman.

Now, let’s look at the two teams expected to be deep in the mix for Judge’s services: the Dodgers and Giants. San Francisco has familial ties, as Judge’s parents only live about an hour and a half way. Judge also grew up cheering for the Giants, who won three World Series the last decade.

However, San Francisco has struggled to find its footing post-Bruce Bochy. Regressing to an 81-81 record after winning 107 games in 2021 isn’t particularly inspiring either. Even Farhan Zaidi builds a new winning culture, adding Judge won’t put the Giants over the top.

That would mean the Dodgers should have a clear advantage, but they have issues of their own. They’re good at winning regular season games, spending money on players, and not much else. Their model is ride playing in a weaker division to 100 or more regular season wins, then almost always fall flat in the playoffs. Not to mention, we’ve already discussed their own financial limitations when it comes to signing Aaron Judge.

Again, advantage Yankees. On top of the offer already made, it’s clear New York is working extra hard to keep Judge. Re-signing his close friend Anthony Rizzo to a new contract was just the beginning. Now is the time to focus on Judge’s accomplishments in New York and how he’s far from finished.

Moreover, forget baseball for a second. It’s clear that Judge really loves New York and, more importantly, his Yankees teammates. His wife just ran the New York City Marathon — no small feat — and both the Rizzos and Giancarlo Stanton showed up to support her. Last season, on a day off, Judge was joined by Rizzo and DJ LeMahieu at a New York Rangers game.

The free agency process will play itself out like it does every year. Judge deserves every right to listen to offers, explore all options, and make the decision that’s best for him and his family.

But at this point, it looks like that best decision is New York. Now, the Yankees just have to want him enough. Cashman, 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.