3 reasons Aaron Judge has every right to leave Yankees in free agency

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A take from earlier in the year that seemed to age poorly might just be turning the corner to blossom into one of the finer tasting wines of this beautiful autumn season. New York Yankees star Aaron Judge is hitting free agency, and it’s once again never felt more real that he could actually leave.

The Yankees have let it get to this point. They’ll now be competing with teams willing to offer the most possible money. There are far more teams with better financial flexibility, too.

On top of that, there are legitimate reasons why Judge shouldn’t come back, which is scary. His three MVP-like seasons have gone to waste with the Yankees falling short in the playoffs — embarrassingly so.

That’s not even cracking our top three, though. The Yankees, who famously never give out contract extensions to players before free agency, decided to do so with Aaron Hicks and Luis Severino. Those two deals blew up in their face. God forbid they prioritized the most important players to the franchise. Can’t possibly do that.

If you’re optimistic Judge will return, that’s great. Most Yankees fans hope he does. It’s just hard to carry over such positivity into an uncertain offseason when this organization has dropped the ball time and time again. There shouldn’t be any surprise if they botch this situation, either, because …

Aaron Judge has many legitimate reasons to spurn Yankees in free agency

New York Yankees General Manager Brian Cashman (Photo by Mike Stobe/Getty Images) /

3. Yankees Didn’t Get a Deal Done in Time

The Yankees knew this was coming. Judge’s impending free agency has been discussed for well over a year now. In 2021, he put to rest his “injury concerns” (which were a couple of freak accidents) with a 148-game campaign where he finished fourth in the MVP voting and won a Silver Slugger. He scored 89 runs, hit 39 homers, and had 98 RBI on the league’s 19th-ranked offense in terms of runs scored.

He was the lone source of consistency in 2021, which saved the Yankees from missing the playoffs. He was the long source of consistency in 2022, which saved the Yankees from choking away a 15.5-game lead in the division.

Judge requested a deal to be done before Opening Day if the Yankees were interested in signing him to an extension. He made it clear after the season ended. Multiple times over the past year he’s expressed he wanted to be a Yankee for life.

Though the Yankees’ offer at the time was indeed fair, Judge bet on himself and won. And now the Yankees have put themselves in a perilous situation. They don’t like overpaying. They don’t like offering long-term contracts. They don’t like offering high AAVs. They could’ve given Judge an extra $40-$50 million to make this stalemate go away, but now they’ll be on the hook for $100 million or more, it seems.

They didn’t prioritize their most important player. Why should he prioritize them?

Aaron Boone #17 of the New York Yankees (Photo by Thearon W. Henderson/Getty Images) /

2. Aaron Boone Will Return

The Yankees have gotten worse under manager Aaron Boone. Whether that’s directly his fault is a conversation for another time. Heck, Brian Cashman is expected to return, too! You know, the foot solider who takes care of Hal’s money and the guy who disrespected Derek Jeter during contract talks toward the end of the Hall of Famer’s career.

The status quo at the top will seemingly remain, per the man Hal Steinbrenner himself.

Judge was the AL MVP runner up back in 2017, his rookie season. At present day, that’s the closest the Yankees have come to reaching the World Series. Cashman’s either improperly built rosters for the postseason, made poor judgement calls, and/or has been cursed with bad luck in his decision making. Judge, for a few postseasons, hasn’t helped the cause either. Since the 2019 ALCS, he’s hitting .168 in 23 playoff games.

But in 2017, it was an underdog squad. That gets a pass. Plus the Astros were cheating. In 2018, they flat-out choked against the Red Sox (and didn’t have enough pitching). In 2019, they didn’t have enough pitching and the offense disappeared (14 runs in the final five games of the series, where they lost four of five). 2020 was a disgrace. 2021 was a result of inexplicable regressions, bad risks (Corey Kluber, Miguel Andújar, Domingo Germán, JAY BRUCE) and poorly miscalculated trade acquisitions (Joey Gallo, Andrew Heaney).

As you can see, it’s not all on Boone. But Boone’s supposed to be a motivator. He’s supposed to bail the Yankees out more times than not when offensive droughts happen; when injuries rock the roster; when unexpected regressions occur.

But he doesn’t. He manages for tomorrow. Opposing skippers run circles around him. His postgame interviews are low energy, full of excuses, all the while lacking baseball acumen. He’s had five years. That’s a long time. It’s gotten progressively worse. It couldn’t hurt to have a new voice and it’s hard to believe Judge is sold on this kind of continuity.

Farhan Zaidi, President of Baseball Operations for the San Francisco Giants (Photo by Victor Decolongon/Getty Images) /

1. Multiple Teams Can (and Will) Offer More Money Than Yankees

Going back to reason No. 3, the Yankees attempted to secure Judge on the lowest-risk-possible deal that limited the length of the contract and tread carefully on the AAV, not to make the cost too prohibitive. Smart? Sure. Necessary? Not when you’re a $6-$7 billion operation.

Judge was offered seven years and $213.5 million. Did we really need that 0.5? Couldn’t round up for the guy?

Anyway, the Yankees’ payroll is an ugly, ugly sight. As of right now, they have about $200 million in guaranteed money already committed to the 2023 season. What?! How?! And if there’s a desire to stay under certain luxury tax thresholds, they will likely do one of two things: avoid a wild bidding war for Judge, or out-bid everyone else and then not properly build around him, ending their offseason there.

With the San Francisco Giants, Chicago Cubs, Seattle Mariners, Boston Red Sox, St. Louis Cardinals and others with a lot of financial flexibility, who says more than one of those teams won’t go higher than the Yankees? And if they do, what’ll that say about the Yankees’ offer, from Judge’s perspective?

Judge also can’t be oblivious to the team’s poor roster construction/decision making. He’s watched them refuse to get as good as they can possibly get because of self-imposed financial restraints. He’s watched Boone continue to give underperformers chances while not rewarding good output from backups, prospects or part-timers. He’s seen the offseason/deadline trades.

If they break the bank on him and he knows the payroll number, don’t you think he might have it in the back of his head that he’ll just be here, treading water, as the Yankees figure out a way to make sure their piggy bank is taken care of before anything else?

Nobody’s asking the Yankees to spend $300 million. They’re asking them to pay the right players, be better with an elevated/league-high budget. and potentially break barriers when mistakes are made and amends need to be made.

But they do none of that. Judge has watched it all happen. And if he wants to win, he might come to the conclusion that this might not be the place.

NEW YORK, NEW YORK - OCTOBER 23: Anthony Rizzo #48 of the New York Yankees fields a hit by Jose Altuve #27 of the Houston Astros during the seventh inning in game four of the American League Championship Series at Yankee Stadium on October 23, 2022 in the Bronx borough of New York City. (Photo by Elsa/Getty Images)

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Aaron Judge has many legitimate reasons to spurn Yankees in free agency

3. Yankees Didn’t Get a Deal Done in Time

2. Aaron Boone Will Return

1. Multiple Teams Can (and Will) Offer More Money Than Yankees

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