Aaron Judge’s Free Agent Leverage Isn’t Just About Money

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It’s no secret that the Yankee universe will orbit Aaron Judge’s free agency this offseason. Every other move New York makes will hinge on the Gordian knot of trying to hold on to the American League’s new home run king. Judge bet on himself and won when he turned down the Yankees’ contract extension offer ahead of the 2022 season. He won big, and now he has unfathomable leverage as he throws in free agency.

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

I’m much more interested in two other ways Judge could wield his influence, which aren’t necessarily financial. Instead, he has a unique opportunity to put pressure on the Yankees if he wants to do his part to ensure the rest of his pinstripe career is optimal.

First of all, any deal Judge signs with New York could be the last contract he signs as a big leaguer. With that in mind, the first way I argue that Judge should cash in on some of that leverage is to make sure, before signing on the dotted line, that the Yankees are actually determined to win. Admittedly, I’m making an assumption in there – that the judge himself wants to win. If all he cares about is who will spend the most money, then if the Yankees offer an extra $10, that’s the ball game.

But if victory is on Judge’s mind (as it seems to be), I think it behooves him to demand a meeting, or series of meetings, with Hal Steinbrenner and Brian Cashman. Joel Sherman of New York Post had the reverse of that idea a few 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 World Series ends.

Regardless of what Steinbrenner does, Judge’s long-term interests would be well served in determining exactly what the Yankees’ vision is for the next decade. And even as I type this, it seems unfathomable that anyone needs assurance that the Yankees are primarily committed to winning championships. For anyone who has followed the club over the past quarter century, the relentless pursuit of World Series titles has been a constant feature.

But alas, here we are. After a 2021 offseason that saw the trade of Isiah Kiner-Falefa and Josh Donaldson rather than inking one of the star shortstops in the free agent market, and after a trade deadline of 2022 in which the Yankees traded for Frankie Montas, seemingly avoiding Luis Castillo, it’s fair to wonder if the Yankees are really worried about winning championships. They may have simply accepted that these half measures are best for their team.

Will the club be more active in finding elite free agents to fill needed positions? How aggressive will the Yankees be in pursuing elite talent in the free agent market? The judge should definitely pin Hal and Cashman down, settling for nothing less than concrete answers. And if he doesn’t like or disagree with the club’s strategic vision moving forward, it needs to be clear he’s unhappy and what his disapproval could mean for the Yankees as they go forward. that his free agency progresses.

But assuming the judge is content with what Steinbrenner and Cashman explain as their plan unfolds, my second suggestion for the slugger builds on that. Opt out. It’s one thing to think you have your finger on the pulse of the organization when you sign with them. But life comes quickly to you. Ask Nolan Arenado how long it took the Colorado Rockies for him to feel disillusioned and be lied to.

The opt-outs are a way for Judge to protect himself if, after signing with the Yankees, he feels they are less than all-in to win championships. And to put maximum pressure on the club, an opt-out is insufficient. Opt-outs after the second, third and fourth years of the agreement? It could be more efficient. Knowing that Judge could pull the exit hatch should he become unhappy with the direction of the franchise could help compel the Yankees to make sure they do everything they can to win, lest their ultra-star superstar marketable goes elsewhere, depriving them of the financial benefits it brings to the team and suffers an almost unimaginable revolt from the fans.

Of course, the Yankees might decide they don’t want to be so beholden to the franchise. Three consecutive opt-outs, for example, may be a bridge too far. At this point, the judge would have a decision to make on the significance of something like this. But it would also be a huge risk for the Yankees, with clubs like the Dodgers, Giants and Cubs all already tied to Judge.

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

The judge enters free agency in a scenario where few athletes find themselves. His performance during his walk year gives him considerable leverage as he begins to make the decision that will help define his legacy. As a Yankees fan, I encourage him to roam Yankee Stadium for the next decade. But I also hope he maximizes every last ounce of upside he has to try to make sure that while he wears stripes, the Yankees do everything they can to help him win multiple championships.

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