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The Tuesday Discussion: Our Favorite Derek Jeter Moments

by SSTN Admin

June 28, 2022

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Amazingly, Derek Jeter turned 48-years-old on Sunday. This week we asked our writers to think back and share some of their favorite memories of Derek Jeter's playing career. Here are their responses...

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Paul Semendinger - I think I have to go back to the very beginning, or almost the beginning. I remember 1996. I was a young teacher, it was Opening Day, and I had a free period or lunch (or something) just as the Yankees game was about to begin. There was no Internet to watch games from, and no classrooms had a TV, but there was one in the library and the librarian allowed me to go into the back room, where the TVs and film strip projectors and all of that stuff was, and watch the game there (at least until I had to rush down the hall to my next class). I remember the anticipation and the excitement that came with the hope of the new season. It had been a literal lifetime since I had seen the Yankees as champions. I had been ten-years-old in 1978, I was a kid. Now I was grown. I still had that hope, that dream, that the Yankees might just win it all one day... And I had this hope that their new young shortstop, this Derek Jeter, might just be the real deal. The years since have obscured my memory, but I remember his over the shoulder catch and I remember his home run. I don't remember if I saw them both live on that little TV. I think I did, but I'm not sure. But I do remember the excitement and the joy and the hope. It turned out that the Yankees were for real - and so was that shortstop.

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Cary Greene - My favorite Jeter moment ever has to be the uncanny "flip play," which occured on October 13th, 2001, in the seventh-inning of the third game of the American League Division Series between the Yankees and the Athletics.


I was living in Brooklyn at the time and of course the city was reeling from the events of September 11th. Somehow, Baseball seemed to unite the city during those somber days. I will never forget having to sweep the dust off of my car, dust that fell as a result of a shift in the wind that blew the plume of smoke coming from ground zero over Brooklyn. By the time the playoffs began, I was in desperate need of some October baseball and the Yankees really gave it all they had that year.


Yankee fans have all seen the play I'm sure and of course Jeter was in the right place at the right time - a sort of one in 100 billion type occurrence and one I had never seen before or since. Indeed, the "flip" is forever seared into my memory.


Terrence Long roped a Mike Mussina pitch down the right-field line and it was fielded by Shane Spencer, who wildly overthrew both cutoff men. As if by magic, Jeter appeared near the first-base foul line, shoveling the ball to catcher Jorge Posada who nailed Jeremy Giambi who was charging home, but failed to slide on the play. A tenuous 1-0 Yankees lead was preserved by Jeter's phenomenal play. It was nothing short of stunning.


I happen to also be a big A's fan so when the two of my favorite teams play, it's always really hard for me to chose a side. However, with the way the Yankees played the game during the Core-Four's dynasty run, I was always 100% rooting for the Yankees. My thoughts heading into that particular series, which is one of the greatest postseason series in Yankee history, were that the A's were clearly a better offensive team. The Mariners had by far the best offense in MLB that season, but the A's were a free-swinging bunch led by Jason Giambi, who was at the peak of "his PED powers."


Oakland also had better overall pitching than the Yankees and in fact, the A's were the second best pitching staff in baseball in 2001. Jeter's play truly changed the momentum in that series and it opened a portal that lead through the then mighty Mariners and all the way to the World Series. The Yankees run that year was as unlikely to occur as Jeter's play was to ever happen.


Jeter called the play "a perfect storm," in that a lot of moving parts had to align to get the ball into his hand. Spencer said that night that he "just wanted to get the ball in quickly," sacrificing accuracy for speed.

Posada has said that if Spencer had just hit one of the two cutoff men, Alfonso Soriano, or Tino Martinez, "We would have gotten him out by a lot." And Giambi made the ill-fated decision not to slide, explaining at the time that "I didn't want to slow down."


"That play, I remember seeing the ball down the line and there was no chance we could make an out at home," Soriano said. "I was the cutoff man with Tino, but the throw was too high. I saw Jeter running to the ball and I thought, 'Whoa, we've got a chance.' An unbelievable play."

"That's one of those plays you talk about," said Bob Melvin, who was the A's manager at the time. "He's got point-guard qualities, where he's just in the right place at the right time. That was probably as being in the right place at the right time as you're ever going to be on a baseball field."


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Mike Whiteman - My favorite Derek Jeter moment was one of the first - his 1996 postseason. Jeter batted .361 across the magical Yankee postseason run, and was unshaken in the glow of the spotlight.


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Ed Botti - Its hard to pick 1 play from a hall of fame career. But, I am partial to the play against Boston at Yankee Stadium when he dived into the stands to make the catch and end a threat. After the play was made, he got back on the field bloodied, while Garciaparra sulked on the Boston bench. A winner that never quit.

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Tim Kabel - I am going to pick something a little different as my favorite Derek Jeter moment. There were so many plays and moments on the field that it would be hard to pick just one.


In December 2002, George Steinbrenner criticized Derek Jeter for doing too much charity work and for spending too many nights out on the town. Basically, the Boss was saying that Jeter wasn’t focused on baseball. It was the first time Jeter had come under criticism from Steinbrenner. Really, it was the first time Jeter received serious criticism from anyone. It had the potential to become a major rift. It was possible that such an incident could have eventually driven Jeter off the team. That’s not what happened. Not only did Jeter resolve the issue, he did it in a classic way.


Derek Jeter and George Steinbrenner Filmed a Visa commercial which parodied the Boss’s blustery persona and Jeter’s fabled nightlife. The commercial ended with Jeter dancing a conga line at a nightclub. Bringing up the rear of the conga line was none other than George Steinbrenner himself.


The issue was out to rest in a classy and amusing way. As with everything else Jeter did, he handled the situation perfectly.


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James Vlietstra - To me, it’s not anything specific that he did. Don’t get me wrong, Jeter could fill a DVD of highlights. I probably went to 250 games at Old Yankees Stadium. My guess is he was the shortstop at 200+ of them. He was the omnipresent professional player, always at the right place at the right time.


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Tamar Chalker - It’s so hard to choose, but I was in the bleachers at Fenway for his very last game and for to see his last hit, so personally, I’d have to go with that. The Flip and the Dive, are up there though.


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Andy Singer - It's almost impossible for me to choose just one Jeter moment. Derek Jeter was my favorite player growing up, and I largely credit his emergence as a star player for my love of baseball above any other sport. However, if I can only pick 1 moment, there's only one I can choose from Derek Jeter's career: "The Flip Play." I was sitting in a family friend's living room staring at the biggest TV screen I had ever seen (I later found out that it was as big as it looked, as I helped move it out years later...but I digress), watching in horror as the ball was hit to right field. Everyone in the room was screaming at the TV, and I could feel a wave of sad acceptance wash over me as I saw the trajectory of Shane Spencer's throw. As Jeter came out of nowhere, I can't even tell you how all of us reacted; I just remember the vague feeling that the room shook, but I may have imagined it. That was such an important play for so many reasons in 2001, and the thought of New York failing to make it to the World Series just felt like it would be another blow to the heart. That play represents everything Jeter was: always in the right spot with just the right amount of magic. Of everything Jeter did in his career, the feeling I had watching the flip play is one for which I can only say, "Thank you."




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