Yankees losing faith in Aaron Judge as he catches them off guard

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Sep 28, 2022; Toronto, Ontario, CAN; New York Yankees designated hitter Aaron Judge (99) watches the play from the dugout against the Toronto Blue Jays during the fourth inning at Rogers Centre. Mandatory Credit: Nick Turchiaro-USA TODAY Sports

The Yankees brass has remained confident in their quest to retain Aaron Judge this off-season, but their hopes are quickly dwindling after the superstar slugger surprised them by reportedly attending the winter meetings in San Diego.

Judge showed up at the Tampa Bay Buccaneers game on Monday night, but flying to the West Coast is certainly a surprise, especially if the Yankees were unaware of his actions.

Andy Martino of SNY reported that Judge caught the Yankees off guard with a trip planned to attend the winter meetings.

“The report that Judge is going to be in San Diego caught the Yankees by surprise. They legitimately do not know why he is coming. They still don’t know why he is coming. And obviously, if you are trying to sign a player that can’t make you feel great.”

The Yankees have a monster offer for Aaron Judge on the table:

The Bombers had an eight-year, $300 million deal on the table recently, but recent reports have suggested a nine-year commitment to the 30-year-old outfielder. Seemingly, Judge is buying his time and trying to drive up his price tag even further. It seems to be between the Yanks and Giants, but if general manager Brian Cashman threatens to bow out of the race, it is possible Judge decides to act quickly and stay with his former team, which has been his preference.

Nonetheless, San Francisco is gaining steam and feeling great about their chances of landing Judge, which certainly isn’t a good sign for New York.

Per Bob Nightengale of USA Today, the Giants are feeling confident in their chances of landing Judge.

“The San Francisco Giants’ confidence is growing in their hopes of signing American League MVP Aaron Judge, with team officials divulging Monday that they have become ultra-aggressive in their talks to land the New York Yankees star.”

Coming off a season where Judge hit .311 with a 42.5% on-base rate, including 62 homers and 131 RBIs, even if he can approach those totals in the future, the contract will be worth every penny. Consider the argument that Judge represented the Yankees’ entire offense during the second half of the year, and they likely would’ve missed the playoffs without him to gauge his value.

A nine-year deal certainly feels hefty, but if the Yankees can capitalize on the first five years of the contract when Judge is still in his prime, it will be worth it. The Bombers have plenty of youth rising through the system, preparing to make a significant impact in the near future, allowing Cashman to spend elsewhere.

Despite the obvious benefits of retaining Aaron, his likelihood of sticking with New York continues to disintegrate with every passing day, especially with the Giants willing to be extremely aggressive for his services.