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Pinstripe Alley Top 100 Yankees: #4 Derek Jeter

The icon of the late 1990s dynasty and Core Four Captain lands fourth on our list of the franchise’s all-time greats.

Baseball - Interleague - Yankees vs. Dodgers Photo by Chris Williams/Icon SMI/Icon Sport Media via Getty Images

Full Name: Derek Sanderson Jeter
Position: Shortstop
Born: June 26, 1974 (Pequannock, NJ)
Yankee Years: 1995-2014
Primary Number: 2
Yankee Statistics: 2,747 G, 12,602 PA, .310/.377/.440, 115 OPS+, 119 wRC+, 3,465 H, 260 HR, 544 2B, 66 3B, 1,311 RBI, 1,082 BB, 73.0 fWAR, 71.3 rWAR


If you were to ask the modern generation of Yankees fans entering adulthood who their favorite player was, the overwhelming result would be Derek Jeter. The face of the franchise at the turn of the century, Jeter’s stoic nature, constant presence near the top of the lineup, and iconic list of postseason success led him to capture the hearts of the fans in Yankee Stadium just as it captured his growing up as a kid in the 80s.

Jeter burst onto the scene as the leading man for a championship core that would immediately wipe away memories of the years in the doldrums that the franchise had been through, and quickly replaced them with the cementing of a modern dynasty that has since been unrivaled in the 21st century of Major League Baseball. He remained near the top of the game for over a decade after, and by the end of his playing days his legacy as one of the best the game has ever seen was secure.

The Kid from Kalamazoo

Derek’s life began in Pequannock, New Jersey, but he moved when he was four to live in Kalamazoo, Michigan with his parents Dorothy and Sanderson Charles Jeter. The couple had met while serving in the army overseas in Germany, and while their relationship blossomed abroad returning stateside brought some harsh realities to light: the country wasn’t particularly accepting of mixed-race couples, and their children would face plenty of hardship for the circumstances of their birth.

Derek had his father’s steady hand to guide him, and Charles did his best to prepare him and his sister Sharlee for the experiences that were sure to come. It wasn’t a complete shield — even after growing up, Jeter would later recall coming home to Kalamazoo after making it to the pros and having the n-word thrown in his face with the force of a physical slap — but it was a part of the structured lifestyle that molded the young boy into the determined man he’d become.

That discipline extended to nearly every aspect of his life growing up. With an accountant for a mother and a father with a doctorate in social work, there was a massive emphasis on education from an early age and Jeter rose to the challenge. He even famously signed contracts with his parents to ensure that he would live up to his end of the bargain in childhood, and Ian O’Connor described his high school deal as pertaining to everything including “phone calls, television hours, homework, grade-point averages, curfews, drugs and alcohol, and respect for others.”

Of course, Jeter’s parents encouraged him to give his all for his extra-curricular activities as well, and he found immense success on the baseball diamond. Jeter took in the game at an early age, spending his summers back in New Jersey with his grandparents, and he caught plenty of Yankees games during that time. Derek fell in love with the team, and channeled that passion into the career he knew he had to get. Coached by his father, a former college shortstop himself, Jeter became a natural in the infield and wowed scouts leading into his senior year of high school by batting .557 the year prior. This was more than just a potential MLB career down the line — Jeter was in line to be the best high school prospect in the country. The No. 1 pick in the draft in 1992 belonged to the Houston Astros, and there was buzz that they were going to take him there, but there was one major concern that MLB front offices had: the University of Michigan.

Derek Jeter in attendance of a Michigan football game, ballcap sitting backwards on his head.
Despite decommitting, Derek Jeter became a lifetime Michigan fan.
Photo by Gregory Shamus/Getty Images

Derek was taking plenty of college visits as his star was rising across the nation, and among several prominent programs he developed an affinity for his hometown team in the Wolverines. He signed a Letter of Intent to play under coach Bill Freehan, and it was viewed as a major gamble for some teams whether they could convince him to forego college for the pros. The Astros, for their part, had a scout named Hal Newhouser begging them to take that risk and pick Jeter, arguing that he’d be the face of a championship core, and when they passed on him to select Phil Nevin instead Newhouser took it as a sign to retire.

Four more teams stood between the Yankees at the sixth overall pick and Jeter, and four more teams chose to play it conservative and go for college prospects instead. The Yankees, who themselves were unsure if they could be the team to get him to sign on the dotted line, had a scout named Dick Groch doing his best to convince the powers that be to make the selection. Tasked with the question of whether it would be possible, Groch offered this famous response:

The Yankees chose to take that risk, and it paid out handsomely. Jeter was convinced to sign after conversing with Freehan (who urged him to make the smartest choice for himself and go pro) and some negotiations over his signing bonus that delayed his arrival to rookie ball, ultimately agreeing to an $800,000 deal. The future cornerstone of the Yankees was in the building, and now all he had to do was make it to the majors.

Developing into a Superstar

Of course, that’s easier said than done even for a player with Jeter’s talents, and his path to the big leagues hit an immediate roadblock in his rookie year of pro ball. His offensive numbers were, frankly, terrible — he posted a .210/.311/.314 slash line in 58 games split between the GCL Yankees and Greensboro Hornets. Even more worrisome were the 21 errors he committed in that short span. He had an excellent arm and a strong physique for the position but he struggled to put it all together consistently, leading to mistakes on most routine plays.

New York Yankees

Given an offseason to rebound physically and mentally from jumping into the proverbial deep end of the pool and managing not to drown, Jeter had already begun to acclimate himself — at least with the bat. He picked it up with a .295/.376/.394 slash line in 1993, exclusively playing 128 games in Greensboro, and ignited the hope that the team had in their first-overall pick. The glovework, however, remained a massive enigma — Jeter showcased dazzling throws and strong range on a variety of highlight reel plays, but his 19-year-old body couldn’t stop getting tumbled around to the tune of 56 errors. The organization wanted him to stick at shortstop, but they were preparing for a future where they might have to move him into the outfield where his cannon arm could shine given a little more reaction time to get to the ball. Jeter, adamant even at that early age that he could improve, swore that shifting off of the position was “never going to happen. Never.” And as ridiculous as it might have sounded at the time, Jeter’s proclamation would prove true in the minors and throughout his career.

Around 1994, everything started to come together for Derek. A lengthy focus on his defense started to produce not only the instincts that he needed to read the ball off of the cut, but he began to finally form a rhythm with his body. His distinctive style of manning shortstop, his energetic jump-throws that awed the crowds and became iconic for shortstops in the generation to come, was solidified down in the Yankees’ instructional league field and buoyed the young blue chip. He cut his errors down dramatically to 25 that year, impressive enough on its own, but he did so while rising through the organization on the merits of his red-hot hitting.

Jeter played in all three major levels of the Yankees’ farm system that year, batting over .300 in each stop and posting a .344/.410/.463 line overall in 138 games. The accolades were coming in now: minor league player of the year, top five prospect in baseball, and a ticket to the Bronx was surely within reach. Perhaps he could’ve forced the decision on his team that year, but the ‘94 strike ended those hopes alongside the remainder of the season, and then the Yankees made the decision to sign Tony Fernández on a two-year deal to be their stopgap shortstop for the major league team in 1995.

Jeter’s momentum was slowed but hardly stopped — he continued punishing the baseball in Columbus and in May, Fernández and fellow infielder Pat Kelly went down with injuries. General manager Gene “Stick” Michael made the call to go get that gangly kid from Kalamazoo a flight out to Seattle, and Derek Jeter joined the Yankee clubhouse officially for the first time. The team laid out the iconic number two jersey for him, signaling their faith that he would be around for a long while to come.

Leading the New-Age Dynasty

On May 29, 1995, penciled into the nine hole in the lineup, Derek Jeter dug into the box for the first time as a major leaguer. He faced Seattle’s Rafael Carmona, and wound up going 0-for-5 that night. The next day, however, brought with it Jeter’s first MLB hit — a single through the hole in short during his second at-bat against Tim Belcher. Jeter got the run at shortstop for 13 games leading into the middle of June, when the expected starters recovered and Jeter was sent back down with an adequate but unspectacular first taste of the bigs.

Jeter went back to Columbus and tore the cover off of the ball, earning a September callup back to the Bronx where he mostly soaked in the experience of a team making a push for the postseason. He appeared in just two more games, but he got to witness the revival of October baseball in New York as the Yankees made their first postseason appearance in 14 years, losing in the ALDS to the Mariners in five games.

All of this set the stage for a 1996 season where the expectations continued to rise. The Yankees made a couple of major changes to their staff, chief among them letting Buck Showalter go in favor of Joe Torre as manager. The new skipper had his eyes on Jeter as their Opening Day shortstop, and to Jeter the job went thanks to an elbow injury Fernández suffered in spring training that kept him out for the entire year. The phenom rewarded the trust put in him immediately, launching his first career home run in a 7-1 Yankees win over Cleveland.

From then on, Jeter was off to the races. He posted an excellent rookie campaign, slashing .314/.370/.430 with 10 homers, 104 runs, and 78 RBI on his way to a unanimous AL Rookie of the Year Award. The Yankees vaulted to the top alongside the core of prospects that had arrived with him, posting a 92-70 record good enough for first place in the AL East and a date with the Texas Rangers in the ALDS. Jeter didn’t flinch at his first taste of the postseason, going 7-for-17 in four games as the Yankees narrowly survived their first test. The ALCS and the Orioles were next up, and Jeter got some infamous help in the opening game of their matchup:

Jeffrey Maier’s uncalled interference wound up being Jeter’s first career postseason home run instead, and it tied the game at one. The Yankees wound up winning the game in extras and the series in five, and Jeter collected nine more hits to go with his homer. His bat was electric, and by the time the Fall Classic began Torre had officially flipped his nine-hitter all the way to the top of the lineup. Their biggest challenge awaited them there, however, in the form of the defending champion Atlanta Braves.

Neither Jeter nor the Yankees had any answers for the Braves in Games 1 and 2, and there was palpable tension in the air heading into Atlanta with the possibility of a sweep strong. Torre, however, famously predicted a sweep for the road team in this stretch, and the Yankees proved him right taking three straight to then clinch the World Series on their home soil in Game 6. Jeter was somewhat quieted in this series, going just 5-for-20 with five runs and one RBI, but the title was theirs and the foundation for a dynasty was in place.

The first title defense for Jeter and the Yankees looked much the same in the regular season, with Jeter putting up solid numbers again and the Yankees boasting 96 wins this time en route to the division title. However, they ran into a wall in the form of Cleveland in the ALDS, losing a closely-contested series in five games. Jeter was one of the few bats to stay consistent, going 7-for-21 with a pair of homers, but the rest of the offense couldn’t find their early success and combined for just five runs in the final two losses. Dreams of a repeat were crushed, but that defeat gave way to one of the greatest teams of all-time.

The 1998 Yankees are neck-and-neck with the Murderers’ Row 1927 team as the greatest in franchise history, collecting 114 regular season wins and stomping their way back to a title. They also boast the first truly elite season of play from Jeter, who made the jump from dependable leadoff shortstop to MVP candidate — a .324/.384/.481 slash line, 19 homers and an AL-best 127 runs earned him third place on the ballot at the end of the year. It also booked him his first trip to the All-Star Game, an honor he’d collect 14 times over his prestigious career, though his friend Alex Rodriguez earned the starting nod at shortstop that year.

Though the 1999 team took a step back in terms of overall firepower, Jeter managed to take another leap forward, earning a career-best 7.4 fWAR for a truly incredible season: a .349 batting average, 24 home runs, 102 RBI, 134 runs, and a league-leading 219 hits. He also extended his on-base streak from the end of ‘98 to a remarkable 57 in a row.

Oddly, Jeter’s jump in production didn’t lead to a jump in the MVP race, as he instead slid down to sixth behind a host of power-pumping bats and Pedro Martinez’s excellent year. Still, Jeter and company collected the ultimate prize, claiming back-to-back titles and their third in four years, and Jeter’s handprint was all over this one — he had at least one hit in every game and went 18-for-53 with 10 runs scored overall.

Jeter remained on top of his game in 2000, earning another All-Star nod and even winning MVP in the Midsummer Classic, but the Yankees endured and persevered through a rough and strange season. The team won just 87 games as mainstays like David Cone and Tino Martinez suffered through poor performance, but the rest of the division malfunctioned enough to give them the AL East crown still. The Yankees’ path to a World Series and a three-peat went through Oakland and Seattle, and Jeter had his first sluggish start to the postseason with only four hits in a nail-biting five-game series victory over the A’s.

The Yankee shortstop got back in gear for the Mariners’ series though, perhaps motivated with the clash against his still-close friend and competitive rival, Rodriguez. The Yankees won in six and secured their place in the Fall Classic once more, but it was a close contest between the two teams and the two shortstops. Jeter more than did his part, posting a .318/.464/.591 line with a pair of bombs, but Rodriguez showed out with a 1.253 OPS in the six games.

A-Rod was on the couch, however, as Jeter and the Yanks got ready for a Subway Series against the Mets that they would take in five games. Jeter saved his best performance for the finale, earning World Series MVP honors after going 9-for-22 with two homers and six runs scored. He is the only player in MLB history to hold All-Star and World Series MVP in a single season.

Crowning of a Captain and the Aughts Mini-Drought

The 2001 campaign for a four-peat took on a dramatically different tone once the events of September 11th played out. Baseball took a step back as the nation attempted to recover from a deeply traumatic day, before stepping up as one of the sources of healing. Once things were fully back in swing after a weeklong pause, the Yankees had another division title and a run-in with some familiar faces in Oakland. This time around, the A’s had a much stronger core in place and immediately put New York in an 0-2 hole.

Down to their last life, neither offense could break through in Game 3 with a single run feeling like it was worth 100. In the bottom of the seventh with Mike Mussina on his last fumes, Terrence Long laced a double to right that should’ve scored a run, until Derek Jeter made this play:

Coming out of nowhere, Jeter had potentially saved the season with one roam down the first base line. The Yankees closed out that game with a 1-0 win, and proceeded to reverse-sweep the A’s before stunning the 116-win Mariners to punch their tickets to a fourth-straight World Series. The Arizona Diamondbacks were all that stood between them and a four-peat under the most unimaginable conditions, and falling down in the series 2-1 the Yankees needed some midnight magic. Down 3-1 in the ninth inning, Tino Martinez saved the game with a two-run home run to propel the World Series into its first-ever action in November, and Jeter punctuated the moment with style:

The newly-crowned Mr. November had given the Yankees life, and that brought them all the way to the doorstep in Game 7, but the stars weren’t aligned for them that year. The Diamondbacks walked them off, and effectively ended an era. The 2002 roster saw significant change with the departures of Cone and Martinez alongside the retirement of Paul O’Neill, turning the page to a new chapter in the team’s history. Midway through the 2003 season, seeking to reinstate for some the vintage magic that the Yankees of old had, George Steinbrenner called a press conference to announce the arrival of a new captain. The Yankees hadn’t had one since 1995 when Don Mattingly retired, fittingly right in time to pass the torch to Jeter, and with him firmly entrenched as the franchise player The Boss decided that the time was right.

The title of captain is one that fits like a second skin to a guy like Derek Jeter — always the one to commit to working on himself, never a critic of his teammates, and leading by example on the field and off. His model for carrying himself is so deeply effective that it has been copied nearly verbatim by his successor on today’s Yankees teams in Aaron Judge, but for all the star power that the current captain carries it’s a miracle that Jeter kept such a level head with his own astronomical level of importance. It’s also a testament to his leadership that he kept his head above water when the Yankees threw a massive curveball at both him and the league in 2004.

Coming off of a second World Series loss in three years, this time at the hands of the Marlins, and with their expected third baseman Aaron Boone suddenly out for the year due to a freak injury playing pickup basketball, the Yankees launched themselves into the A-Rod sweepstakes and landed the superstar.

This A-Rod, however, had a significantly different relationship with Jeter than the one the two shared just a few short years ago — the friendship had gone frosty after Rodriguez secured the biggest deal in baseball history with the Rangers and decided to throw a shot at Jeter in the media scuffle over it. This part of the story is more conducive of Rodriguez’s behavior and his career, and our own John Griffin covered it well in our entry for him, but there is something to say about Jeter at this moment — Rodriguez was the better shortstop when he joined the team, and as Jeter previously stated he would never let go of that position. His iron will won out in that contest, and A-Rod joined the team with the understanding that it was third base or nothing for him.

Sadly, for all of the offensive firepower that the mid-2000s Yankees carried with them, the teams themselves flamed out due to a severe lack of pitching behind ace Mike Mussina. Jeter continued to carry his own weight on the field and in the batter’s box, including a 2006 campaign that saw him get his closest bid to an MVP award with a second place finish behind Justin Morneau, but the team didn’t come close in ALDS losses across the board from 2005-07.

The 2008 campaign would be the last in the original Yankee Stadium, and though the Yankees would miss out on the postseason altogether, Jeter was in the lineup for the final All-Star Game to be played on those hallowed grounds. He also closed the house down with a memorable off-the-cuff speech on the field after the finale on September 21st.

A Final Ring, a Fitting Conclusion

Spurred on by their failure the previous year, the Yankees loaded up for the 2009 season. With newcomers CC Sabathia, Mark Teixeira, and A.J. Burnett in pinstripes the time was now to compete for a ring, and Jeter had a vintage performance to help lead the way. In his age 35 season, Jeter collected 6.7 fWAR and hit .334 as the Yanks roared to a 103-win year that saw him finish third in AL MVP voting. The Captain notched the first playoff homer at the new Yankee Stadium as the Twins were brushed aside in the ALDS, and the Angels were no match in the ALCS either.

The defending-champion Phillies were the last foe standing between Jeter and his fifth ring. All he did was hit 11-of-27 in the series, the second-best hitter beside the supernova that was MVP Hideki Matsui. The Core Four had converged on another title, and the window was open for more.

Unfortunately for them, the window closed abruptly for them. The 2010 season ended in an ALCS defeat at the hands of the Rangers, but is perhaps more memorable for the passing of two icons for the franchise in July: owner George Steinbrenner and longtime public address announcer Bob Sheppard. Steinbrenner had a reputation for quarreling with his stars but had mostly gotten along famously with Jeter, and Sheppard’s iconic voice had preceded all of Jeter’s iconic moments at the plate. At Jeter’s request following Sheppard’s retirement in 2007, a recording of Sheppard’s voice was used to announce him for the remainder of his career, a touching sendoff from a legend of the game to a legend in the booth.

Jeter’s bat had lagged behind significantly in 2010, putting up his worst wRC+ as a full-time starter at 93 — for the first time in his career, Derek Jeter had been below-average. He made it back above that line in 2011, just in time to reach an incredible milestone: 3,000 hits. Reviving that vintage swing of his for an afternoon, Jeter tee’d off on David Price and the Tampa Bay Rays, going 5-for-5 and making, as Michael Kay would exclaim, history with an exclamation point:

The personal accomplishment was easily the highlight of the year for the Yanks, and it was a hefty weight off of Jeter’s shoulders after the shortstop had been pressing for the final couple of hits he needed for days. The Yankees retook the division title but failed to do much in October, bowing out in the ALDS. 2012 saw Jeter, even at 38 years old, capable of collecting a league-best 216 hits and earning down-ballot MVP talk, but his year came crashing down when he broke his ankle near the end of Game 1 in the 2012 ALCS. The Yankees folded shortly after, getting swept, and 2013 proved to be a nightmarish season health-wise for Jeter, who returned midseason only to deal with hamstring and calf issues that limited him to a paltry 17 games.

Facing down his baseball mortality, Jeter announced ahead of the 2014 season that it would be his last. He managed to push through 145 games, swinging a mostly-ineffective bat and now truly hampered on the field, but he stuck to his guns and weathered it out at shortstop. The Yankees had become a truly mediocre team by the point, finishing with 84 wins and without a ticket to the postseason for the second consecutive year, but they stayed in the race officially until the final week of play. In his final start at Yankee Stadium that year, Jeter walked up to the plate with the Yanks having just given up the lead but with the winning run now in scoring position. What else could you expect for the man who made a career full of clutch hits?

Jeter’s ride into the sunset fittingly came to a conclusion at Fenway, where he played in the final two games and was pulled midway in both. The last hit of his career came on September 28, 2014 against Clay Buchholz, an RBI single to third. The storybook career had its ending, not in a climactic blaze of glory but a satisfying resolution.

Post-Playing Days

Jeter took the opportunity to step away from the spotlight for a while after his retirement, fading away to enjoy life down in Tampa. Eventually though, the desire to be involved in the game again grew, but unlike many former players he did not go the route of coaching or broadcasting (initially). Instead, Jeter joined up with businessman Bruce Sherman and company to purchase the Miami Marlins, and he was named CEO of the organization. Jeter’s tenure as a baseball owner was a strange contrast to his career — relying solely on the talents of others, Jeter struggled to put together a winning ballclub and clashed with several of his advisors and scouts. He sold his stake in the team ahead of the 2022 season and stepped down as CEO with just one year recording a record over .500 in 2020, and was in power when the Marlins oversaw a fire sale of their highly talented outfield including MVPs Giancarlo Stanton and Christian Yelich.

In 2020, Jeter was on the ballot for the Baseball Hall of Fame for the first time, and was inducted with a near-perfect ballot of 99.7 percent of the vote, just one shy of a clean sweep. Had his teammate Mariano Rivera not made history as the only player to be unanimously inducted the previous year this might have been more controversial, as there is a long and drawn out history of the BBWAA playing politics with some slam dunk candidates, but instead Jeter soaked in the joy of earning the biggest accomplishment the game of baseball has to offer. After such a incredible career, becoming an icon for the sport and one of the faces of the most successful franchise in sports where the legends before him already stood so tall, that sure is a lot to celebrate.

Staff Rank: 4
Community Rank: 6
Stats Rank: 5
2013 Rank: 5


Baseball America

Baseball Reference

Cohen, Alan SABR Bio


Kernan, Kevin. “The what, where, and how of Jeter’s iconic jump throw.” New York Post. Sept 24, 2014

Kornacki, Steve. “Derek Jeter - A Michigan Man Despite Never Playing for U-M.” Aug 27, 2014.

Neschis, Matthew. “Derek Jeter shares racism he faced: ‘I remember being so hurt.’” New York Post. July 12, 2022.

O’Connor, Ian. The Captain, The Journey of Derek Jeter Mariner Books, 2011.

Parker, Rob. “Jeter and The Boss delivered titles.” ESPN. July 16, 2010.

Unruh, Jacob. “Meet Dick Groch, the scout who signed Derek Jeter.” The Oklahoman. June 27, 2015.

Wilkins, Randy. “The CaptainESPN. July 18, 2022.

Young, Matt. “ESPN’s The Captain’ brings up painful Derek Jeter story for Astros fans.” Houston Chronicle. July 19, 2022.

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