During the summer, when the uncertainty over Aaron Judge‘s future had begun to build up, many fans were angry over the team’s failure to sign the slugger for a long term. Michael Kay’s seven-year-old son Charlie had made it clear to his father that his support for the Yankees was conditional subject to Aaron Judge playing for them.
According to ESPN, Michael Kay asked his son, “You wouldn’t cheer for the Yankees anymore, even though your dad calls the games for the team?” Charlie responded. “Yes.”
Later that day, the reporter went up to Aaron Judge to tell him the story, and he saw real pain flashing across the power hitter’s face. And the slugger said, “Tell Charlie not to be afraid.”
This made Michael Kay the only person in the Yankees’ world to have any idea what Aaron Judge wanted. Else, his public actions were hard to figure out. The AL MVP deflected questions about how he was about to become a free agent by talking about the team. Judge never complained in public and never brought attention to himself. Day after day, the power hitter played well on the field, and his value rose as he got closer to and then passed Yankees legend Roger Maris’ American League home run record for a single season.
Aaron Boone, the manager of the New York Yankees, said during the first weekend of the season that Aaron Judge would be able to handle the attention that would be paid to him during his “walk year.” However, Judge’s ability to separate his contract situation from the rest of his life—his mental strength—went above and beyond what some club officials had seen from other players.
At the end of a disappointing AL Championship Series, when Judge went 1-for-16 and Yankees fans booed him, a staff member told him that the team really wanted him back. He told the batter that the team would do whatever it could to keep him. But when they talked, Aaron Judge was not sure what to say. After the World Series, he was no longer a Yankee and could sign with any team.
GM Brian Cashman got owner Hal Steinbrenner to take part in the talks himself. Because so much money was at stake and the offers could go through the roof, the owner needs to have things in his perspective. Steinbrenner could raise the team’s offer in an instant by a lot if he needed to.
Steinbrenner and the player met twice in Florida after the playoffs, and the Yankees’ first improved offer was $300 million over eight years, or an average of $37.5 million per year, which was slightly more than Trout’s deal. Later, this offer would go up to $320 million, or $40 million a year.
But when Aaron Judge’s comments to Time magazine came out the day before he made his decision, the Yankees were shocked by how frustrated he seemed. Time Magazine interviewed the slugger after naming him “Athlete of the Year”. In that interview, Judge said he didn’t like the way Cashman told the press about him turning down a seven-year, $213.5 million contract offer.
“We kind of said, Hey, let’s keep this between us,” the slugger spoke to Time. “I was a little upset that the numbers came out. I understand it’s a negotiation tactic. Put pressure on me. Turn the fans against me, turn the media on me. That part of it I didn’t like.”
That made the Yankees wonder if Judge would ever play for them again. “I had that feeling that we were going to lose him,” an unnamed Yankees official told ESPN.
There were reports that the Mets talked about Aaron Judge among themselves and met with his agent, Page Odle, at the GM Meetings in November. However, they told Judge’s team, according to the report, that they were more interested in starting pitchers. The meeting happened after an SNY report said the Mets were not interested in Judge only to help the Yankees. This led MLB to look into whether the two teams were working together, but the league found no evidence of this.
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