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25 Smartest Moves of the Past 25 Years: Yankees extend Derek Jeter

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Sometimes, the right move is to stand pat.

BBA-SPRING TRAINING-YANKEES-JETER Photo by PETER MUHLY/AFP via Getty Images

Had the lockout not turned the hot stove into the frozen wasteland of Hoth, the biggest topic of conversation surrounding the Yankees would be the impending free agency of the face of the franchise Aaron Judge, the 2017 Rookie of the Year with three All-Star appearances and two top-six MVP finishes to his name as he enters his final year before free agency.

If this sounds familiar to long-time Yankees fans, well, it should be. Around this time 21 years ago, the Yankees faced a similar conundrum with their starting shortstop and face of the franchise, the 1996 Rookie of the Year with three All-Star appearances and two top-six MVP finishes to his name as he entered his final year before free agency prior to the 2001 season. You might remember his name — Derek Jeter. Last time around, the Yankees got right to work, put pen to paper, and inked the future captain to a 10-year extension that kept the most important member of the franchise in pinstripes through at least the 2010 season.

Signing Details: Signed to a 10-year, $189 million extension

Transaction Date: February 9, 2001

Stats over length of contract (2001-10): .310/.380/.445, 156 HR, 315 2B, 26 3B, 215 SB, 1,000 K, 607 BB, 117 OPS+, 41.3 bWAR, 8-time All-Star; 2020 Hall of Fame inductee

During the 1999-2000 offseason, the Yankees had reportedly floated a seven-year, $118.5 million offer in the general direction of their starting shortstop. However, because George Steinbrenner did not want to set a record for highest salary, the deal fell through when Detroit’s $143 million extension for Juan González also did. Jeter proceeded to have another great campaign, slashing .339/.416/.481 with a top-10 MVP finish en route to the Yankees’ three-peat (keyed by Jeter’s World Series MVP performance).

If the Yankees wanted to keep No. 2 in the two hole, they were going to have to pay up, and in the end, they did. The final extension was $1.5 million more annually than the original offer, along with three additional years tacked on at the end. It was the second-highest contract in baseball at the time, trailing future teammate Alex Rodriguez, who had just signed a mammoth deal with the Rangers earlier that winter. The man who would become known as the Captain came out ahead from the Boss’s stubbornness.

From the very beginning, the extension started to pay dividends. Much like the 2000 Yankees, the 2001 squad was not the high-flying offense that fans had become used to during the dynasty years, carried more by their pitching staff than a deep lineup. Despite a team OPS+ of 100 (ranked eighth in the AL), they ranked fifth in the AL with 804 runs scored. Jeter’s presence as a table-setter atop the lineup — in front of the trio of Bernie Williams, Tino Martinez, and Jorge Posada — was a major reason for the success, and he ended the season with 110 runs scored.

Jeter’s real impact, however, was seen in that postseason with a pair of historic plays. As the Yankees faced elimination in Game 3 of the ALDS against the 102-win Oakland Athletics, Terrence Long came to bat against Mike Mussina in the seventh with Jeremy Giambi on first and two out down by one run. Long laced the ball into right field, and as Shane Spencer missed the cutoff man, Giambi tried to score from first. And then ... well, you know what happened next:

“The Flip,” as it came to be known, preserved the lead for the Yankees, who held on to win the game. They ultimately proceeded to mount a comeback, winning three straight to advance to the ALCS with Jeter making another remarkable play in the clincher.

After taking down the 116-win Seattle Mariners in the ALCS, the Yankees went on to face the Arizona Diamondbacks, looking for their fourth straight World Series victory and fifth in six years. Unfortunately, the baseball gods were not with the Yankees, who lost the World Series in heartbreaking fashion, but even so, Jeter came through in a big way.

Having fallen in an 0-2 hole after the first two games in Arizona, the Yankees sought to even the series in Game 4’s matchup between Orlando Hernández and Curt Schilling. Down 3-1 going into the bottom of the ninth, the Yankees scored two off Diamondbacks closer Byung-Hyun Kim, courtesy of a two-out, two-run Tino Martinez home run, to force extra innings. With two outs in the bottom of the tenth, Jeter came out on top in a nine-pitch at-bat to earn the moniker “Mr. November.”

Despite how the series ended, these moments have been enshrined in Yankees lore. Over the course of the extension, Jeter built his legend. He has the signature highlight of one of the greatest regular season games of all time, the epic 13-inning matchup between the Yankees and Red Sox on July 1, 2004 ...

... set the new record for most hits as a Yankee with 2,722, passing Lou Gehrig ...

... and was a critical part of the Yankees’ return to the top in 2009, hitting .334/.406/.465 with 6.6 WAR and finishing third for AL MVP, behind only winner Joe Mauer and new teammate Mark Teixeira.

Named the captain in 2003, Jeter received the honor of speaking on behalf of the team following the final game at the old Yankee Stadium.

Not surprisingly, Jeter’s Yankees tenure did not end with the conclusion of his contract, as he was signed to a three-year deal with a fourth year option following the 2010 season (although it was a negotiation much more tense than it should have been). Nonetheless, when those of us born during the dynasty years think back on the career of the Captain, it is the years of this contract, the years in which he cemented his Yankees legacy and established himself as one of baseball’s all-time greats.

Sometimes, the right decision isn’t to make a change, but to keep the status quo. When it comes to a captain in his prime, you don’t need to overthink things — and fortunately, despite George Steinbrenner’s best attempt, the Yankees didn’t.