Jeter\u2019s reputation as a defender had outpaced his actual ability for the vast majority of his career, but by this time it was public knowledge, written about and indeed commented on by Cashman, who after the signing admitted Derek may be ticketed for the outfield to play out the remainder of his career. With all that in context, the Yankee GM went public with the free agent process, advising Jeter through the media that he would be wise to entertain offers from all bidders.<\/p>\n
On its own that\u2019s pretty standard, but this wasn\u2019t a standard free agency case. Jeter had advised his agent not to seek out other offers, that he was a Yankee and was going to stay one. Despite giving up nearly all leverage, Derek\u2019s camp was frustrated<\/a> on multiple occasions by Cashman and Co. stonewalling during negotiations, and public reports that Jeter\u2019s \u201csalary demands\u201d were \u201cgreedy.\u201d When Jeter asked Cashman point-blank who he\u2019d rather have at the six, he replied \u201cTroy Tulowitzki<\/a>,\u201d as the Colorado shortstop was in his mid-twenties prime. It\u2019s interesting to sit with all this reporting 15 years on, knowing what we know about aging curves, but also trying to imagine what it would be like for an older Aaron Judge to be a looming free agent.<\/p>\n There are players who you back up the Brink\u2019s truck for, but those guys tend not to be in the mid-to-late 30s. There are players who you extend for as long as you can, but Jeter was already in decline and getting worse. Then there are players who you never want to see wearing any other jersey, and The Captain is perhaps the ur-example of this \u2014 a final season wearing a Reds or Royals uniform would have left a bad taste in everyone\u2019s mouths.<\/p>\n While that maelstrom of circumstances was always going to make for a complicated free agency, Cashman\u2019s consolidation of control only made things more difficult. The organization today is built almost entirely in the GM\u2019s interest, and by all accounts he will remain functionally in charge of the Yankees until he doesn\u2019t want to be anymore. The groundwork for that level of control started to be laid in the waning days of Joe Torre\u2019s managerial tenure, but really came about as Hal and Hank began signing the checks.<\/p>\n Brian Cashman is not the worst GM in baseball\u2014he is not even in the bottom half\u2014but he does have some tells. When he really wants someone, the Yankees tend to get him, like the successful pursuit of Gerrit Cole in December 2019. When he really doesn\u2019t, it\u2019s a flat take-or-leave offer, the kind given to Robinson Can\u00f3 (or in the case of Gleyber Torres, no offer at all). Given all that, it\u2019s not impossible to conclude that Cashman would have preferred Jeter to walk, holding firm at three years and $45 million. He would eventually concede another six million total, plus an option year, but it took in-person meetings<\/a> with Hal and Jeter\u2019s camp before those wounds closed up.<\/p>\n TAMPA, FL – DECEMBER 07: Shortstop Derek Jeter of the New York Yankees (2L) shakes hands with General Manager Brian Cashman (2R) during a press conference to announce his new contract with the club on December 7, 2010 in Tampa, Florida. (Photo by Tim Boyles\/Getty Images) Getty Images<\/p>\n![\"TAMPA,](\"https:\/\/www.rawchili.com\/mlb\/wp-content\/uploads\/2026\/02\/gettyimages-107379234.jpg\"\/)
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