Why Yankee Shortstop Prospects Didn’t Like Derek Jeter

Special Contribution by Richard Cuicchi

October 3, 2023

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One of the most revered players in the game, Derek Jeter fell one vote short of being a unanimous Hall of Fame selection in 2020. Inducted into the Hall in 2021 (delayed one year because of the pandemic), he took his place among the all-time greats. He played 20 seasons with the Yankees, one of the longest tenured players in their storied history. From 1995 to 2014, he was a member of five World Series championship teams.

When you think about Jeter’s longevity, you have to wonder how many shortstop hopefuls for the Yankees didn’t get a chance for a steady job in the big leagues because Jeter was a permanent fixture in the position, year after year.

Shortstop prospects must have cringed when their name was called by the Yankees on MLB Draft Day. They had to figure their chances of displacing Jeter were close to zero percent. Do you think they ever wished that Jeter would have a premature career-ending injury in order to open up the position? Did they try to change to another infield position to avoid being backlogged by Jeter?

When Jeter made his major-league debut in 1995, 33-year-old veteran Tony Fernandez was the regular shortstop for the Yankees. Fernandez was a one-year rental by the Yankees, so it was inevitable the Yankees would look elsewhere for their next shortstop. Andy Fox and Robert Eenhoorn were contemporaries of Jeter in the minors in 1995 and would have also been candidates as Fernandez’s replacement. Fox had been a second-round draft choice by the Yankees, but he wound up switching to second base, teaming with Jeter to form the double-play combo for one season. He played only 11 games at shortstop in his two seasons with the Yankees. Eenhoorn, also a second round pick, played a total of 20 games over three years for the Yankees, including a handful at shortstop.

Over the next years with Jeter firmly entrenched at shortstop, the Yankees front office continued to use relatively high draft picks for shortstops. Seth Taylor was a fifth-round pick in 1999. Bronson Sardinha was a first-round supplemental pick in 2001. Andy Cannizaro was a fifth-round pick in 2001. C.J. Henry was a first-round pick in 2005. Corban Joseph was a fourth-round pick in 2008. Angelo Gumbs was a second-round pick in 2010. Cannizaro was the only one who played shortstop for the Yankees, and that amounted to only 10 games. All of these players were ultimately traded or released by the Yankees.

Not counting his first season in 1995 and an injury-plagued season in 2013, Jeter was an “Iron Man” of sorts, averaging 150 games per season. When his name wasn’t on the lineup card, the Yankees primarily used veteran utility infielders to backfill him. Reserve players like Luis Sojo, Miguel Cairo, Ramiro Pena, and Eduardo Nunez filled the bill. When Jeter played only 17 games in 2013, Nunez and journeyman infielder Jayson Nix took his place, not some new shortstop-in-waiting from the Yankees farm system.

When Texas Rangers shortstop Alex Rodriguez, a two-time Gold Glove winner, was acquired by the Yankees in 2004, it was A-Rod who changed positions, going to third base, not Jeter.

Jeter was a 14-time all-star and five-time winner of both the Silver Slugger and Gold Glove awards. He ranks sixth in all-time hits (3,465). He was MVP of both the All-Star Game and World Series in 2000.

When Jeter retired in 2014, fans wondered how the Yankees would ever backfill the legendary shortstop. Their answer was 25-year-old Didi Gregorius whom they acquired from Arizona. Practically anyone the Yankees put in the position would have big shoes to fill. Gregorius was somewhat of a gamble, never having put in a full season with the Diamondbacks or the Reds in his three big-league seasons. But Gregorius rose to the challenge and put in four solid years with the Yankees before sitting out half of 2019 recuperating from torn cartilage in his wrist. He signed as a free agent with the Philadelphia Phillies for the 2020 season.

Jeter was the face of baseball during his prime playing years. He played on baseball’s biggest stage in New York City and led the Yankees to some of the biggest victories in the franchise’s history. He was a beacon of light for Major League Baseball throughout the turbulent PED era. As he said during his Hall of Fame induction speech, he always tried to play the game the right way and to have respect for the game.

Jeter won over countless fans throughout his career. But there were also numerous Yankees organization shortstops who wished he wouldn’t have been so good for so long.

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Contributed by Richard Cuicchi, richard@thetenthinning.com; SABR member since 1983.