Derek Jeter's 8 most unforgettable moments

New York Yankees legend Derek Jeter will receive one of the highest honors in sports on Sunday. The iconic shortstop, who led the Yankees to five World Series championships, will have his number retired by the team.

It’s a fitting honor for one of the greatest players of his era. For 20 seasons, Jeter defined the Yankees. Nicknamed “The Captain,” Jeter was lauded for his demeanor and leadership in the clubhouse. His on-field accomplishments — 13 All-Star appearances, eight Gold Gloves and the 1996 Rookie of the Year award — are equally impressive.

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And yet, simply listing his career numbers doesn’t do Jeter justice. He had a knack for coming when his team needed him the most. Most players would kill for one career-defining moment. Jeter seemed to produce a new one each year.

With that in mind, we asked the Yahoo Sports staff for their favorite Derek Jeter moments. Below, you’ll find a list of some of the iconic plays that defined Jeter’s exceptional career.

Derek Jeter had plenty of celebratory moments during his excellent career. (AP)

In retrospect, it makes perfect sense that Jeter received a storybook ending in his final game at Yankee Stadium. His career mirrored that of every hero in every fairy tale. He accomplished great feats, won exceptional battles and made himself into a legend.

Jeter was clearly at the end of his rope during his final season, but still found one last opportunity to conjure some magic in front of his home crowd. With a man on second, and the game tied 5-5 in the bottom of the ninth, Jeter stepped to the plate for one more battle. On the first pitch, he seemed to transform into his younger self. Jeter slapped a base hit to right, scoring a run from second and picking up the walk-off hit in his final game at Yankee Stadium.

Michael Kay’s call of moment was perfect. As Jeter was being mobbed by teammates, Kay exclaimed, “Derek Jeter: Where fantasy becomes reality.” It was too perfect an ending. The whole thing seemed scripted, but that was just Jeter. His tale was always going to end in triumph. He was always going to conquer evil one more time and live happily ever after. (Chris Cwik, Big League Stew)

Growing up in the Bronx during the 1990s, it was nearly impossible to think of something Derek Jeter and the Yankees hadn’t done. Sixteen years after I had initially fallen in love with the sport – and the hometown bombers – I once again found myself with my jaw agape thanks to “The Captain.” After a rainout on Friday night, there wasn’t a cloud in the sky on that picturesque Saturday afternoon. Jeter stepped into the box in the bottom of the third inning, Yankees trailing 1-0 against David Price, sitting just one hit away from 3,000. Jeter worked the count to 3-2 before Price made a mistake, hanging a breaking pitch and Jeter drilled it into the left-field seats.

Michael Kay perfectly called it, “history with an exclamation point.” All I could muster was, “oh my God” in a mass text. It was a moment of pure elation and disbelief.

In the 100-plus year history of the Yankees, no one had ever amassed 3,000 hits. In the 150-plus year history of baseball, only Wade Boggs had ever hit a home run for his 3,000th hit. The moment was another example of Yankees magic. The Captain’s blast would become perfectly ironic when four years later, Alex Rodriguez did the same – yet again playing second fiddle to Jeter. (Anthony Sulla-Heffinger, Yahoo front-page editor)

You didn’t have to be a Yankees fan for this moment to give you chills. Four minutes after the clock struck midnight and baseball season ventured into November for the very time during the 2001 World Series, Derek Jeter delivered an iconic moment, hitting a walk-off home run in Game 4, and Michael Kay delivered an iconic call, anointing Jeter as “Mr. November.”

Though the Yankees would ultimately lose the classic series to the Arizona Diamondbacks in seven games, that moment has endured as much as any other Jeter moment, or any Yankees postseason moment, because of the emotions involved. At the time, New York was still reeling from the Sept. 11 terror attacks, which forced MLB to push its entire schedule back one week. That’s when November baseball became a possibility. It became a reality thanks to some late-inning heroics from Tino Martinez. And that entire night became unforgettable thanks to Derek Jeter. (Mark Townsend, Big League Stew)

What made Jeter great was his ability to exceed the big moments. Jeter had that thing only the best, most memorable athletes had. Was it clutch? Was it luck? Was he just born under a better sign than everybody else? Whatever it was, Jeter always seemed to make the most of those moments.

The one that proves Jeter’s greatness was less about luck was his famous play in the 2001 ALCS against the Oakland Athletics. The Flip, they call it. Say it and any baseball fan past the age of 15 or so should know what you mean. It’s just one of those sports moments where two simple words — The Flip — makes the whole thing replay in your brain.

You don’t really need the play-by-play on this thing, because you know what happened. But just remember that Jeter wasn’t supposed to make that relay. He rushed in to save the day when the throw missed the cut-off man and wasn’t going to get Jeremy Giambi at the plate. He darted in, to redirect that ball, to get that out, to make Oakland hate him forever. That wasn’t luck. It was being present in the big moment. Something Derek Jeter always seemed to be. (Mike Oz, Big League Stew)

Arguments about Derek Jeter’s defensive value will continue long after the sun burns out and life on this planet is but a distant footnote in the history of the universe. Even so, Jeets undoubtedly had a few defensive gems, and perhaps his best was his running catch on July 1, 2004 that resulted in a headlong dive into the stands.

It was a perfect play to sum up Jeter for a number of reasons. For one it was clutch, the grab prevented two runs in an extra-inning game — which for even more bonus points was against the Red Sox. Also, he showed no hesitation to put his body on the line in service of the Yankees and ended the play bleeding from the face. Perhaps best of all, A-Rod started the play closer to where the ball landed, but just jogged a few steps back and watched Jeter steal the show. (Nick Ashbourne, Yahoo Sports Canada)

You hate Derek Jeter because his luck was better than your team’s luck. You hate him because it wasn’t enough that he had all the talent in the world, but he benefitted from plays that were so far out of his control you don’t even need to mention his name to know what we’re talking about.

Exhibit A: The Jeffrey Maier Home Run. The controversy had really nothing to do with Jeter — this was more of a failure on the part of the umps in the 1996 ALCS between the Yankees and the Orioles — and yet it lives on in Jeter lore because of course Derek Jeter was the beneficiary. All The Captain did was hit the ball to the right spot and run the bases. He didn’t tell young Jeffrey Maier to interfere with the play or the umps to miss the call. Jeter was told he hit a homer and trotted around the bases with his head down like it was nothing.

It’s not just that Jeter was good enough to lead his team to the playoffs. He created all of his own luck, too, once he got there. You could only appreciate his talent, but the true hatred came from the luck that Jeter seemed to have in endless supply. (Blake Schuster, Big League Stew)

Regardless of how you feel about the New York Yankees, there are two Bronx legends that have earned the respect and admiration from all baseball fans: Derek Jeter and Bob Sheppard.

The late public address announcer — dubbed “The Voice of God” by Reggie Jackson — was just as iconic of a figure at Yankee Stadium as Jeter, Mantle, Ruth and DiMaggio. “The Captain” became so enamored with Sheppard’s distinguished pipes that before his retirement in 2009 at the age of 98 (!), Jeter asked Sheppard to record an introduction that would live on every time No. 2 stepped to the plate. That recording made a special appearance during the 2010 MLB All-Star Game, just two days following Sheppard’s death.

“Now batting for the American League … from the New York Yankees … the shortstop, number two, Derek Jeter … number two.”

It was a touching tribute and show of respect to the only voice he heard throughout his 20-year Yankee career. (Marcus Vanderberg, Yahoo Sports MLB editor)

Derek Jeter dealt with some interesting rumors throughout his career. (AP)

My favorite Jeter moment is easily the gift basket rumor from 2011. The idea that he gave all of his conquests a gift basket upon leaving his apartment seemed so completely insane and farfetched, but at the same time it also felt like it could be true. He’s Derek Jeter, the handsome, classy, smooth-talking Yankees shortstop. Of course he’d have a parting gift for his one-night stands!

Jeter has, of course, denied the rumors several times. But the detail that he included a signed baseball? That just feels so very … Jeter. In fact, the whole thing, right down to the gift basket, feels very Jeter. And the most Jeter thing about it? As reported by the New York Post in 2011, Jeter enjoyed the company of a woman and gave her a gift basket the next morning, not realizing he’d slept with her once before and had already given her an identical gift basket.

On or off the field, Jeter is a total pro: it doesn’t matter how many times a woman comes to his apartment, she gets a gift basket every single time. (Liz Roscher, Big League Stew)

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Mike Oz is the editor of Big League Stew on Yahoo Sports. Have a tip? Email him at or follow him on Twitter!

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