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New York Yankees fans have wondered from time to time why the Yankees haven’t locked up young talents like Aaron Judge, Gary Sanchez, and others. The answer is likely to surprise fans; it doesn’t have that much to do with the player, it’s the owner. Plain and straightforward, Yankee owner and managing partner Hal Steinbrenner doesn’t believe in it. That’s not to be said that it hasn’t been done, but it does suggest why the Yankees engage in contract extensions so seldom.
This past year was an exception. Aaron Hicks was a season away from free agency at the time, though the outfielder chose to forego the open market in favor of a new contract that paid him $64M in new money through the 2025 season.