On November 1st of 2013, the Yankees did one of the most natural things imaginable for the organization, deciding once again that Derek Jeter would be the shortstop for the following season. At the time it wasn’t clear, but it turned out to be the final time the organization would make that call, as Jeter announced just before 2014 Spring Training that it would be his final campaign.

The one-year, $12MM contract struck between the Yanks and their aging franchise icon kicked off a dramatic farewell tour, brought Jeter’s fantastic career to a close, and wrapped up an interesting transactional history between the two sides. His first big contract — ten years, $189MM — came one year after the sides had seemingly agreed to a lesser deal that ultimately wasn’t consummated by owner George Steinbrenner.

In the 2010-11 free agent period, Jeter was already a Yankee legend but was coming off of a poor season as he entered the open market. It took a bit of gamesmanship — MLBTR’s Mark Polishuk called it a “tug-of-war” before the month of November was out — before the sides finally agreed to a three-year, $56MM deal. (GM Brian Cashman said this on November 23, 2010: “He should be nothing but a New York Yankee,” Cashman said. “He chooses not to be.”) There was drama even after that deal was struck, too, with chatter about moving Jeter to the outfield (see here and here) and discussion of hurt feelings.

Heading into 2013, it seemed that Jeter might again command a multi-year pact. He was fresh off of a productive and healthy 2012 in which he slashed .316/.362/.429. But the aging star managed to appear in only 17 games in 2013, with a variety of leg injuries keeping him off the field.

Complicating matters was a player option that was ultimately valued at $9.5MM by operation of incentives provisions. Negotiations weren’t contentious this time around, but nevertheless proved as complicated as anything the sides had previously arranged due to CBA considerations that still seem unclear in retrospect. (Want to have a crack at understanding it? You can check out all the contemporaneous reporting right here.)

Ultimately, the deal didn’t pay off from an on-field perspective. Though Jeter made his 14th All-Star game, that was an honorary nod — albeit one that delivered some memorable moments. He did still play nearly every day, wrapping up his career with a .256/.304/.313 batting line over 634 plate appearances. And New York’s second place finish in the AL East wasn’t enough to snag a Wild Card spot.

Of course, that tepid finish did little to change the fact that Jeter enjoyed an unbelievable run with the game’s most iconic franchise. All told, he took over 12,000 plate appearances over two decades and compiled a lifetime .310/.377/.440 batting line with 260 home runs. He helped lead the organization to five World Series titles, and racked up 71.8 wins above replacement by measure of both fWAR and rWAR. Jeter is a surefire first-ballot Hall-of-Famer, with the only question now is whether he’ll become the first player to receive unanimous support in his first year of eligibility.

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