The Yankees almost always have one of the highest payrolls in the sport. Even as the Mets and Dodgers have shown them that there’s another level to spending, the Yankees routinely are big players in free agency, and some of the greatest free agent signings in history have signed on to play in the Bronx.
Some of those signings, as you’ve seen earlier in this series, were the Yankees trying to retain their own talent. A downside to the way the Yankees operate is that a lot of their stars hit free agency. Bernie Williams, Derek Jeter, Mariano Rivera, and Robinson Cano had all hit free agency in the 25 years prior, and while the first three were all retained, Robbie Cano went to Seattle for a contract that didn’t age well.
So when Aaron Judge declined an extension offer in spring training and bet on himself, only to put up one of the greatest seasons in modern history, the Yankees were forced into winning a bidding war for an MVP superstar hitting free agency. There were some tense moments along the way, but Judge was wooed back to his chambers in the end.
Aaron Judge
Signing Date: December 7, 2022
Contract: 9 years, $360 million
We all know the story of Judge’s path to free agency, but for the sake of posterity, here’s a quick refresher. A three-sport athlete in high school, the 6-foot-7 behemoth attended Fresno State and flashed incredible raw tools that made him a first-round pick in 2013.
After being a low-level top-100 prospect in the minors, Judge was promoted to the majors on August 13, 2016, as the corresponding move to Alex Rodriguez’s retirement. He would homer in his first at-bat in a memorable moment with Tyler Austin, but otherwise struggled in his first cup of coffee in the bigs.
An offseason of uncertainty was all there would be for his career, as he snagged the starting right field spot in spring training and had one of the greatest rookie seasons in MLB history, smashing a then-rookie record 52 home runs and coming second in a controversial AL MVP race.
A few injury-plagued seasons and a healthy, solid 2021 season later, Judge was one year away from free agency. He was one of MLB’s best hitters and a very good defender in right field when healthy, but the health was still a question, as was the fact he was going to be 31 at the start of his next contract. How would his body hold up?
After almost no contract negotiations prior, things heated up prior to the 2022 season. Judge and the Yankees nearly went to a messy arbitration, but avoided it (unlike a certain team from Detroit with their star in 2025). After unsuccessful negotiations that spring, Judge shut down the possibility of an in-season extension and Brian Cashman made a bold move: going public with a contract offer.
Was a seven-year, $213 million pact a fair deal for Judge’s resume entering the 2022 season? I think you can make the case, but this was an interesting leverage ploy for the long-tenured GM, trying to get fans to side against Judge and provide a negotiating cushion if the hulking all-star faltered and came back to the table.
This ploy… did not work. Despite a slow April by his standards, Judge unlocked something new with his game, going from a perennial 40-home run, 5-6 WAR hitter to the best hitter in the world overnight. 62 home runs, 11 WAR, his long-awaiting first AL MVP award. A man who was known early in his career for striking out way too much nearly won the Triple Crown, that’s how sensational he was.
This was, objectively, a disaster for Yankees’ brass. By going public in spring, they hurt their relationship with Judge and his agent, Page Odle, and now would have to pay up for a player who had suddenly become the best free agent in a generation.
There were several suitors. Fortunately, one of them wasn’t newly-minted Mets’ owner Steve Cohen, for whatever reason. In hindsight, maybe Cohen should’ve used his tremendous wealth to go after Judge instead of giving Justin Verlander even more AAV at the exact same time.
The most logical suitor? His hometown San Francisco Giants, who he grew up rooting for as a kid. They wanted to make a big free agent splash, and he was the logical choice. They were willing to give him the godfather offer, nine years and $360 million. It would be the biggest free agent contract in MLB history.
The second big suitor was the late Peter Seidler and the San Diego Padres, who met with Judge at December’s Winter Meetings. An official offer being given out is disputed, but several reports in the years since have suggested that Judge was presented with a deal worth over $400 million. While Seidler’s relentless desire to make his team better, regardless of market size, is admirable, Judge never seemed that interested.
There was relative silence aside from this on Judge’s free agency early on. That was until Tuesday night, when Jon Heyman shocked the baseball world… with a typo.
“Arson Judge” was quickly deleted and corrected, but the message stood. Judge was heading to San Francisco. Mass panic ensued… for about five minutes. Heyman corrected and apologized for jumping the gun. Nobody knows who leaked the information to Heyman, but for those who were online during that time, it was potentially the most panic-inducing few minutes in Internet history for Yankees fans.
The Yankees had an eight-year, $320 million offer on the table for Judge, but with better offers from the Giants and Padres on the table, he wasn’t accepting that. Impatient, and probably fearful after the Heyman news, Hal Steinbrenner called Judge from Italy, wanting to get this done right now. Using his unbridled authority, he went around Cashman and directly offered Judge the ninth year and the captaincy. For the first time since Jeter hung up the cleats in 2014, the Yankees had a captain. Judge agreed to the deal, which was announced Wednesday morning.
On a personal note, I remember exactly where I was when I got the notification. I was in a high school history class. My history teacher was also a big Yankees fan, and we had talked about the team and Judge’s free agency before and after class. After he talked about the anniversary of Pearl Harbor to start the class, I blurted out that Judge had re-signed. It was definitely bad timing, and that’s on me, but it’s something that I’ll remember as part of the frantic process for a long time.
Judge is well on his way to not only having his No. 99 retired and enshrined in Monument Park, but being a first-ballot Hall of Famer. Despite Dodger Stadium severely injuring his toe in 2023, Judge has picked up two more MVPs and logged back-to-back 10 WAR seasons in his first three seasons of the nine-year deal, while continuing to be the face of baseball’s most historic franchise.
See more of the “50 Most Notable Yankees Free Agent Signings in 50 Years” series here.