Yankees rumors: Aaron Judge, Derek Jeter burned by same Brian Cashman tactic

NEW YORK, NY - MAY 14: Derek Jeter greets Aaron Judge #99 of the New York Yankees during the retirement ceremony of his number 2 jersey at Yankee Stadium on May 14, 2017 in New York City. (Photo by Al Bello/Getty Images)
NEW YORK, NY - MAY 14: Derek Jeter greets Aaron Judge #99 of the New York Yankees during the retirement ceremony of his number 2 jersey at Yankee Stadium on May 14, 2017 in New York City. (Photo by Al Bello/Getty Images) /
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SAN DIEGO — It appears that general manager Brian Cashman once again didn’t get the message about putting contract numbers for New York Yankees superstars out in the open. Now that may be one of the things that hurts him and the franchise as Aaron Judge makes his decision between the Yankees and San Francisco Giants this offseason.

Yankees rumors: Brian Cashman may have once again made another serious mistake in negotiations with Aaron Judge

What kind of mistake was made? According to both Aaron Judge and Derek Jeter, the two Yankees legends had asked New York’s front office to keep any kind of numbers out of the public eye when it came time for contract negotiations. It appears that, with both players, that request was ignored.

Let’s start with the reigning American League MVP. Judge has said that he believes contract negotiations were “private between my team and the Yankees” but also acknowledged that “Cash has a job to do.” That was back in April when Judge turned down a $213.5 million contract extension. It appears that those feelings didn’t subside over the season, with a similar refrain coming out on Tuesday in a TIME magazine article as Judge was named as the magazine’s Athlete of the Year.

That was in 2022. Rewind the clock back to 2010 when Jeter was heading to free agency and you will see a similar pattern regarding contract numbers slipping into the open.

“I’m going to be honest with you guys, the thing that bothered me the most was how public this became,” Jeter said at a news conference after signing a new deal in 2010. He recently explained that anger a little more, and shed some light on what was going on behind the scenes.

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While Cashman is among the longest-tenured executives in MLB history, it’s clear that he and the Yankees front office have made some major mistakes when it came to the handling of numbers with at least two superstars. It didn’t keep Jeter from leaving the Bronx, but Cashman could well have the tactic backfire in his face if Judge packs his bags to start a new chapter of his career in San Francisco this offseason.