How Aaron Judge can capitalize on his record-breaking leverage

It’s no secret that the Yankee universe will orbit around Aaron Judge’s free agency this off-season. Every other move New York makes will be contingent on the Gordian Knot of attempting to retain the American League’s new home run king. Judge bet on himself and won when he turned down the Yankees’ contract extension offer prior to the 2022 season. He won big, and now, he has unfathomable leverage as he embarks into free agency.

Perhaps the most obvious — and honestly least interesting — form his leverage will take is as it pertains to the size of the contract that he ultimately signs. $300 million? $400 million? Eight years? Ten years? Who knows. But with multiple suitors expected to be in the running for Judge’s gargantuan bat, the final numbers could be staggering.

I am much more interested in two other ways Judge could exercise his leverage, which are not necessarily financial. Instead, he has a unique opportunity to exert pressure on the Yankees if he wants to do his part to ensure that the rest of his career in pinstripes is optimal.

First and foremost, any deal that Judge signs with New York could be the last contract he ever inks as a big leaguer. With that in mind, the first way I argue that Judge should cash in some of that leverage is by making sure, before he signs on the dotted line, that the Yankees are actually committed to winning. Admittedly, I am baking an assumption into this — namely, that Judge himself wants to win. If all he’s worried about is who will spend the most money, then if the Yankees offer 10 extra bucks, that’s the ballgame.

But if winning is front and center for Judge (as it appears to be), I think it behooves him to demand a meeting, or a series of meetings, with Hal Steinbrenner and Brian Cashman. Joel Sherman of the New York Post had the inverse of this idea a couple of days ago, arguing that Hal should set up a meeting with Judge to talk to the superstar and try to get a deal done before the end of the World Series.

Regardless of what Steinbrenner does, Judge’s long-term interests would be well-served to pin down exactly what the Yankees’ vision is for the next decade. And even as I type this, it seems unfathomable that someone should need assurances the Yankees are primarily committed to winning championships. For anyone who’s followed the club for the last quarter-century, the relentless pursuit of World Series titles has been a consistent hallmark.

But alas, here we are. After a 2021 off-season that saw the trade for Isiah Kiner-Falefa and Josh Donaldson rather than inking one of the star shortstops on the free agent market, and after a 2022 trade deadline wherein the Yankees traded for Frankie Montas, seemingly eschewing Luis Castillo, it’s fair to wonder whether the Yankees are truly worried about winning championships. They might have just accepted that these half-measures are what’s best for their team.

Will the club be more active in pursuing elite free agents to fill positions of need? To what degree will the Yankees be aggressive in pursuing elite talent on the free agent market? Judge should absolutely pin Hal and Cashman, settling for nothing less than concrete answers. And if he does not like or agree with the strategic vision of the club moving forward, he should be clear that he is displeased and what his disapproval could mean for the Yankees as his free agency progresses.

But assuming that Judge is content with what Steinbrenner and Cashman elucidate as their plan moving forward, my second suggestion for the slugger builds off that. Opt-outs. It is one thing to think you have your finger on the pulse of the organization when you sign with them. But life comes at you fast. Ask Nolan Arenado how long it took for the Colorado Rockies to make him feel disillusioned and lied to.

Opt-outs are one way that Judge can protect himself if, after signing with the Yankees, he gets the sense they are less than all-in on winning championships. And to put maximum pressure on the club, one opt-out is insufficient. Opt-outs after the second, third, and fourth years of the deal? That might be more effective. Knowing that Judge could pull the escape hatch if he becomes unhappy with the direction of the franchise might help compel the Yankees to ensure that they are doing everything they can to win, lest their ultra-marketable superstar go elsewhere, deprive them of the financial benefits he brings to the team, and incur an almost unimaginable revolt from the fanbase.

Of course, the Yankees could decide that they’re not willing to be this beholden to the face of the franchise. Three straight opt-outs, for example, may be a bridge too far. At that point, Judge would have a decision to make on just how important something like that was. But it would also be an enormous risk for the Yankees, with clubs like the Dodgers, Giants, and Cubs all already linked to Judge.

Again, all of this could be completely meaningless. There is a myriad of factors that could affect where Judge signs. Geography, money, tax regimes, and so on and so forth. And one or more of those could lead him to leave New York. But if he wants to be a Yankee, the path is there.

Judge is entering free agency in a scenario where few athletes ever find themselves. His performance in his walk year allows him to command considerable leverage as he begins to make the decision that will help define his legacy. As a Yankees fan, I am rooting for him to roam Yankee Stadium for the next decade. But I also hope that he maximizes every last ounce of advantage he has to try and ensure that while he’s wearing pinstripes, the Yankees are doing everything they can to help him chase multiple championships.