Aaron Judge

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Last week, owner Hal Steinbrenner held a one-on-one meeting with Aaron Judge to underscore the Yankees’ commitment to bring back the newly minted American League Most Valuable Player awardee to the fold. “I do believe [the star center fielder] wants to be a Yankee. I think we’ve got a good thing going here,” he said. As far as he’s concerned, there should be no restraint in talks with the free agent, not even other pressing commitments. “We know where we’re at, and I can tell you that that’s not going to stop us.”

For the Yankees, the good news is that Judge clearly wants to keep wearing pinstripes. And he has cause to do so; after all, his seventh year in the Bronx yielded a record-breaking season that highlighted his favorable position as the presumptive captain of the franchise. The bad news is that he could have been inked to a contract extension prior to the 2022 campaign had he been slated to receive the same blank check now being promised.

True, the Yankees’ proposal of $213 million through seven years ending 2029 was nothing to scoff at. Judge could have signed then. Instead, he declined the option and figured that he would produce monster numbers to justify suitors’ frenzied jockeying for position. That he went on to shatter the single-season home run benchmark in the AL, hitherto held by fellow Bomber for 61 years, affirmed the gamble he took. He bet on himself, and is now poised to reap the dividends.

Considering the humility with which Judge has approached the game, there is every reason to believe that his first choice is to stay with the Yankees. That said, he fought for, and earned, the right to maximize the possibilities. Certainly, it’s why he went through the wringer and rejected the path of least resistance. Which, notwithstanding Steinbrenner’s deep pockets, could spell disaster. And unless and until he affixes his Hancock on a new contract, it’s anybody’s guess on what the future holds.

Anthony L. Cuaycong has been writing Courtside since BusinessWorld introduced a Sports section in 1994. He is a consultant on strategic planning, operations and human resources management, corporate communications, and business development.