50 Most Notable Yankees Free Agent Signings in 50 Years: Derek Jeter

How do you negotiate a contract with THE star player?

Not a star player, not a guy you love having around, but the face of the club and indeed arguably at the time the face of baseball itself? How do you negotiate while at the same time attempting to secure personal control over the sport’s most valuable organization?

These were the questions Brian Cashman was forced to grapple with after the 2010 season, when the Captain, Derek Jeter, was a free agent for the first time in his career. George Steinbrenner’s passing the year before meant control of the team went to Hal and Hank, George’s sons, but neither brother really operated — or in Hal’s case, continues to operate — with the same kind of fire, for better and worse. Randy Levine and the other lizards in the executive suites held various roles of course, but Cashman was in the thick of making the Yankees his team, and picking a very public fight with the fifth or sixth most important player in team history was one part of establishing that control.

Derek Jeter
Signing Date: December 7, 2010
Contract: 3 years, $51,000,000

It would be a little silly of me to recap Jeter’s career before he hit free agency, since most anyone reading this can probably recite it chapter and verse. The key leadup to the signing started in 2009, where the then-35 year old put up a 6.7 fWAR season, finishing third in AL MVP voting, winning the AL Hank Aaron Award, getting named SI Sportsman of the Year, and of course winning his fifth World Series with the club. It would be the last truly great season for Jeter, and despite an All-Star nod and Gold Glove in 2010, that campaign would be his worst since 1996.

Hitting coach Kevin Long was instrumental in adjusting Jeter’s stride, and down the stretch he managed to his .342 in his final 80 PAs. But the writing was on the wall — at 36, The Captain no longer was who he once had been as his 10-year extension came to a close. That said, he was still The Captain.

Jeter’s 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.

On its own that’s pretty standard, but this wasn’t 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’s camp was frustrated on multiple occasions by Cashman and Co. stonewalling during negotiations, and public reports that Jeter’s “salary demands” were “greedy.” When Jeter asked Cashman point-blank who he’d rather have at the six, he replied “Troy Tulowitzki,” as the Colorado shortstop was in his mid-twenties prime. It’s 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.

There are players who you back up the Brink’s 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 — a final season wearing a Reds or Royals uniform would have left a bad taste in everyone’s mouths.

While that maelstrom of circumstances was always going to make for a complicated free agency, Cashman’s consolidation of control only made things more difficult. The organization today is built almost entirely in the GM’s interest, and by all accounts he will remain functionally in charge of the Yankees until he doesn’t want to be anymore. The groundwork for that level of control started to be laid in the waning days of Joe Torre’s managerial tenure, but really came about as Hal and Hank began signing the checks.

Brian Cashman is not the worst GM in baseball—he is not even in the bottom half—but 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’t, it’s a flat take-or-leave offer, the kind given to Robinson Canó (or in the case of Gleyber Torres, no offer at all). Given all that, it’s 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 with Hal and Jeter’s camp before those wounds closed up.

While they did close, it always felt like those wounds scabbed over instead of fully healing. Despite joining the 3,000 Hit Club in July 2011, Jeter was largely middling and hurt. He responded with a very nice 2012 that saw him lead the league in hits with 216, albeit while not being quite the productive forced that he was in 2009. And of course he ended the season as painfully — physically and emotionally — as you can, with a late-season bone bruise leading to a broken ankle in extra innings of Game 1 of the ALCS against Detroit.

Jeter would never again play in the postseason. The Yankees were swept, and his injury recovery carried over into various ailments that limited his 2013 to just 17 games. That year was an October-less farewell tour for longtime teammate Mariano Rivera, and Jeter followed suit with his own somber swan song in 2014 after signing a final one-year deal. The ultimate team player, the perfect interviewer, Jeter was naturally frosty and closed off to the media and his superiors within the organization, but that feeling grew in his final years. I don’t think he ever really got over the perceived disrespect, nor did he ever maintain a relationship with Cashman the way he did with Torre or George Steinbrenner.

In the end, both sides ended up being right. Derek Jeter should have never played for any team other than the Yankees, and he never did. Cashman was also pretty on point in seeing the decline coming, even if he probably didn’t imagine quite how bad that final 2014 season would be. Overall, it was an impossible position for Cashman and Jeter, but they managed to pull out a solution.

I think Derek Jeter has been very skilled in crafting his public persona, certainly in a way his contemporaries like Alex Rodriguez couldn’t. I’m also not the biggest fan of Brian Cashman as a person. It would have sucked an incredible amount to see those last, great moments of Jeter’s career, the 3,000th hit, that final walk-off, happen anywhere else. In the end, they happened in the Bronx.

See more of the “50 Most Notable Yankees Free Agent Signings in 50 Years” series here.