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The Yankees Owe Aaron Judge More Than Just Money

In what may ultimately be the biggest front office blunder in franchise history, the Yankees are wasting their superstar captain’s prime by failing to build around him.

If there’s one thing you can count on from the current-era New York Yankees, it’s that they will do that absolute bare minimum necessary to field a semi-competitive team. Even in 2023, a year in which the Yankees are in serious danger of finishing below .500 for the first time in more than two decades, they were at least good enough to be in the American League Wild Card mix at the trade deadline (something the organization ignored entirely).

It’s a far cry from the George Steinbrenner-era “win at all costs” mentality, and it’s a reason why the New York Daily News — the New York sports paper of record — is calling for his kids to sell the team. Last offseason, the Yankees did what they had to do to ensure they’d sell enough season tickets to pad their wallets, re-signing Aaron Judge to a nine-year, $360 million deal and naming him team captain.

Anyone who has watched this team regress since coming within a game of the 2017 World Series knew that was not enough to build a title contender. Nor was it enough to sign the injury-prone Carlos Rodón. But the Yankees stopped there, entering the season with an upside equivalent to their ALCS embarrassment last year and a downside that we are now watching play out in real time.

You can argue whether or not the Yankees have failed their fans these past few years, often passing up on free agent talent and acquiring stop-gap options like Isiah Kiner-Falefa and aging veterans like Josh Donaldson. But one thing is clear:

Despite giving Aaron Judge $40 million a year, the Yankees have failed him, seemingly from the time he was called up in 2016.

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Baseball isn’t a sport where one superstar can drag the corpse of a team to the biggest stage. The Yankees have committed well over a quarter-billion dollars to Judge in return for asking him to spend the full prime of his career in pinstripes. In addition to that investment, however, the club owes him an honest effort to field a championship team.

The problem isn’t that the Yankees won’t spend money; it’s how they spend money. Their payroll ranks the second-highest in baseball and ownership isn’t exactly suffering.

The moves they’ve made just haven’t adequately addressed the holes that exist around Judge.

Consider that left field has been a problem in this lineup for years and the Yankees haven’t found a suitable solution, or that the offense has been too dependent on right-handed hitters for years in a stadium that favors lefties. Note that while Giancarlo Stanton is often either hurt or ineffective, Judge lacks true protection in the lineup. Meanwhile, injuries continue to mount and the analytics department walks around permanently with egg on its face. Even when it feels like rock bottom, the big decision-makers all keep their jobs.

The club always needed to sign Gerrit Cole prior to 2020 (nine years, $324 million) and re-sign Aaron Judge last offseason despite the astronomical salary numbers attached to both. Losing out on Judge would have alienated the fanbase entirely and probably cost the team money down the line when you account for postseason earnings, media exposure, ticketing, in-stadium sales, etc. As for Cole, it was well-known that general manager Brian Cashman coveted him for years and that the player himself grew up as a Yankees fan. Bringing him in was an easy call for a team that, at the time, could have been just one great pitcher away from its first World Series title since 2009.

And for some of these moves, hindsight is 20/20. Rodón was the best free agent pitching option available outside of Jacob deGrom. As it turns out, most of his first year in pinstripes has been a waste due to injury. Other moves, however, have been completely baffling.

It all starts with letting manager Joe Girardi go and replacing him with Aaron Boone, who had no such experience. In Boone’s time at the helm, every young non-Judge prospect to come up to the Show has regressed. His tenure has additionally been marred by base-running and defensive lapses that ultimately fall on the on-field staff.

In 2018, the Yankees decided against pursuing any major free agents in what was one of the greatest classes of all time. They never seriously chased Manny Machado or Bryce Harper, enjoying varying levels of success with their alternatives: DJ LeMahieu won the 2020 batting title and had a great first few years in pinstripes, while Miguel Andujar regressed and Troy Tulowitzki played five games before suffering a career-ending injury.

That offseason, they also went all-in on outfielder Aaron Hicks, signing him to a seven-year, $70 million deal after he posted the first (and only) complete, starter-quality season of his career. Things got so bad for Hicks in 2023 that the Yankees were forced to release him amid nightly boos from the hometown crowd.

It was the continuation of a pattern that carries through to today. While the Yankees’ offense around Judge has continued to fade, particularly in October, Cashman and Co. let guys like JT Realmuto, Corey Seager, Kris Bryant, Starling Marte, and Carlos Correa sign elsewhere.

The offensive moves they’ve made instead have been disastrous, even setting aside Hicks. Trading for then-36-year-old Donaldson in 2022 is perhaps the worst decision of all — they brought in the aging veteran for $23 million per year, and they gave up catcher Gary Sanchez and fan-favorite Gio Urshela to do it.

Somehow, the pitching decisions have been even worse. Instead of going after guys like Corbin, Kevin Gausman, Marcus Stroman, or Jacob deGrom in free agency, the only splash the team has made since acquiring Cole was swooping in for Rodón, which to this point has not paid off. Neither has trading Jordan Montgomery for outfielder Harrison Bader, or trading for Frankie Montas last year.

So, where does this all leave Aaron Judge at this point? Well, he is in his age-31 season, his seventh in the big leagues. He likely only has a few years of prime production left, and at this point, this Yankee roster is such that there’s no real reason to believe the team will contend within that window of time unless a major philosophical change is enacted at the front office level. Meanwhile, he is still the team captain, and fair or not, how this team performs under his captaincy will have a direct impact on his legacy.

The Yankees have 27 World Series titles and it would be a shame to see Judge go through his entire career — currently on a Cooperstown trajectory — without a ring.

The Yankees are giving Aaron Judge a lot. Somehow, they owe him far more.

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About The Author
Russell Steinberg
Russell Steinberg
Russell Steinberg is an editor and writer at Boardroom. He came to the brand in 2021 with a decade of experience in sports journalism, primarily covering college basketball at SB Nation as a writer, reporter, and blog manager. In a previous life, he worked as a social media strategist and copywriter, handling accounts ranging from sports retail to luxury hotels and financial technology. Though he has mastered the subtweet, he kindly requests you @ him next time.