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The Kalamazoo Kid is headed to Cooperstown

Derek Jeter fulfilled a lifelong dream playing for his beloved N.Y. Yankees, and produced countless Hall of Fame-worthy moments

Editor’s Note: The COVID-19 pandemic forced the Baseball Hall of Fame and Museum in Cooperstown, N.Y., to postpone the 2020 Hall of Fame induction ceremonies—originally slated for this summer—until July 25, 2021. Sports Collectors Digest is honoring the 2020 Hall of Fame class with a series of articles about these baseball legends who sat down earlier this year and talked about their careers. Ted Simmons is featured in the June 19 issue and Larry Walker in the July 3 issue. Now, here is SCD’s look at Derek Jeter’s illustrious career:

What will you see when you look at Derek Jeter’s plaque in the Baseball Hall of Fame? Like a great work of art, it will appear different to everyone who views it. Besides a sculpted likeness of Jeter, the plaque will contain a wonderfully written narrative about the New York Yankees legend. Those carefully crafted words will offer more information about Jeter than you ever thought could possibly fit in such a small space.

But so much more will come to mind when you’re transfixed by that bronze tablet. All those magnificent memories, the breathtaking plays, the dramatic hits, the game-winning heroics—all those timeless, priceless recollections will flood back to you. They won’t all be engraved on the plaque, but you’ll see them there anyway. It’s a lot to take in, just like Jeter’s career.

But before he turned into the face of the national pastime, Jeter, like so many of his fellow Hall of Famers, encountered some rough patches. There were plenty of “oh no” moments as the lanky, young baseball player from Kalamazoo, Mich., built his career step-by-step. Yet with the sheer determination that made him a superstar, Jeter overcame those obstacles to greatness, and rose to the top of his field.

Even to this day, Jeter takes nothing for granted. No matter how much certainty surrounds an event—for example, his getting into the Baseball Hall of Fame this year—Jeter still harbors doubts. He insisted that doesn’t stem from insecurity, saying, “I’m just big on trying not to jinx things.”

Jeter poses in Monument Park during the retirement ceremony of Jeter's jersey No. 2 at Yankee Stadium on May 14, 2017. Photo by Elsa/Getty Images

Jeter poses in Monument Park during the retirement ceremony of Jeter's jersey No. 2 at Yankee Stadium on May 14, 2017. Photo by Elsa/Getty Images

So for the past five years, the time a player has to wait between retiring and getting onto the Baseball Writers’ Association of America’s (BBWAA) Hall of Fame ballot for the first time, Jeter never spoke about getting into Cooperstown. “The only time I really ever talked about it during my career or after was jokingly with Reggie Jackson. We had a great relationship and he used to come to the ballpark and he’d walk by me and say, ‘You’re not in the Hall of Fame yet.’ Because we would go back and forth and joke with each other. But that was the only conversation I ever had about it with any players or anybody else.”

Will he talk about it now? “Whew, yeah, we can talk about it now,” Jeter said in a post-announcement press meeting, flashing his famous smile and laughing.

The 14-time All-Star and five-time world champion admitted that he was pretty nervous waiting for the call in mid-January 2020 surrounded by family and friends. “Everyone told me it (getting into Cooperstown) was a foregone conclusion. I didn’t buy it, so it was not a relaxing day. There was a lot of anxiety. I was nervous sitting around waiting for a phone call about something that was completely out of my control.”

What did he say when he got the news? “I don’t even know if I said anything for a while, because it is the ultimate honor and it’s a very humbling experience. To be elected into the Baseball Hall of Fame is truly a dream come true.”

Some 28 years before, Jeter waited for a different momentous phone call that many thought he’d get. But Jeter wasn’t so sure the phone was ever going to ring. That was the day the then-17-year-old Jeter waited to hear if his dream of becoming a New York Yankee would come true. On that day June 1, 1992, five teams in the MLB Draft had picks before his beloved Yankees.

Jeter had been named the top high school baseball player in the nation by USA Today in 1992. He batted .508 for Kalamazoo Central High School Maroon Giants. Even before his senior year, the Kalamazoo Kid had already locked up a full scholarship to play at the University of Michigan, coached by Detroit Tigers great Bill Freehan. Jeter had also garnered lots of attention from pro baseball scouts. Would they lure him away from the Wolverines?

Jeter hits a two-run homer against the Twins in the 2009 ALDS at Yankee Stadium. Photo: Nick Laham/Getty Images

Jeter hits a two-run homer against the Twins in the 2009 ALDS at Yankee Stadium. Photo: Nick Laham/Getty Images

From what Jeter was hearing, he would be selected long before the Yankees ever had a chance to pick him, despite his known preference to join the Bronx Bombers. The most likely suitor was the Houston Astros, who had the first pick. It was between Jeter and Cal State Fullerton third baseman Phil Nevin. Houston picked Nevin.

Then, the Cleveland Indians and Montreal Expos passed because of pitching needs, Baltimore Orioles passed because they had Cal Ripkin Jr., and Cincinnati Reds passed because they had Barry Larkin, though experts still thought they’d take Jeter. But for some reason only the Yankee gods know for sure, the Reds took outfielder Chad Mottola, clearing the way for the Yankees to pick Jeter.

Jeter learned of his selection via a phone call from a reporter. He recalled being in disbelief and overcome with joy, as being a Yankee was almost the only thing he ever talked about since he was a little boy.

How do you get from Kalamazoo to New York? Well, New Jersey can take some credit.

Jeter was born in Pequannock, N.J., and lived in the Garden State until he was 4 years old. The family moved to Kalamazoo so Derek’s father, Charles, an alcohol and drug abuse counselor, could complete his work on a PhD at Western Michigan University. Charles, by the way, played shortstop as an undergraduate at Fisk University in Nashville, Tenn. Hearing stories of his father’s collegiate playing days made Jeter want to emulate his dad and play shortstop as well. While Derek and his sister Sharlee spent the school year in Kalamazoo, they spent summers with their maternal grandparents, William and Dot Connors, who had a large property in West Milford, N.J.

“My mom had 13 brothers and sisters, so every summer I spent time with my cousins in New Jersey. My grandmother was a huge Yankee fan and that’s who got me to love the Yankees.” Jeter’s grandmother went to games at Yankee Stadium and saw the likes of Joe DiMaggio when the Yankees seemed to be world champs every year. Jeter remembers getting his grandmother up early most summer mornings and begging her to play catch with him. She always obliged.

As for his grandfather William, a hard-driving maintenance worker, Jeter said, “Seeing his work ethic helped mold me as a person.” But it was Grandma Dot who watched all the Yankees games with her young grandson and cultivated a diehard Yankee fan who idolized the team’s star at the time, Dave Winfield. “It was those summers in New Jersey (late 1970s-1980s) that not only made me a baseball fan, but a Yankee fan.”

Every summer Jeter would tell his grandmother he would one day play for her favorite team, so you can just imagine how thrilled the family was when he was drafted by the Yankees. On June 28, 1992, two days after his 18th birthday, Jeter signed with the Yankees for $800,000. The 6-foot-2 shortstop, who weighed only 159 pounds, reported for rookie ball in Tampa, Fla., for his first pro baseball experience. It didn’t work out too well.

With the Gulf Coast Yankees in the Gulf Coast League, he saw his first action in a doubleheader on July 2. He went 0 for 7, striking out five times. After playing baseball in Kalamazoo his entire life, “All of a sudden, I’m playing against the greatest players in the world and I was completely overmatched. It was a learning experience with growing pains and you have to overcome it.” He had trouble hitting the curve, and even fastballs were baffling.

For Jeter, the lessons were difficult, the learning curve steep, and much of it centered around dealing with failure. “Because, growing up, some people don’t ever really have to deal with failure. But knowing how to deal with it prepared me for what was to come in New York.”

Jeter also struggled in the field. Playing badly, coupled with being away from home and on his own for the first time in his life, rocked Jeter’s confidence. He began to have doubts about whether he was the right man for the only job he’d ever wanted in his life. He wondered if he should have gone to the University of Michigan for some seasoning before turning pro.

“When people ask me if I ever thought I’d make it to the Baseball Hall of Fame, I remember back to that summer of 1992 when I was just thinking about making it to 1993.” He recalled going back to his hotel room after Gulf Coast League games in 1992 and spending hours on the phone with his parents. He also remembers that he was often in tears. But his parents always reassured him, told him not to get down on himself, to stay positive, to stick with it, to stay focused on his goal, and to keep working hard. They did that no matter what time of day or night he called.

His parents also visited him several times in Tampa in the summer of ‘92. It wasn’t easy for any of them, he recalled, adding that the reward came years later seeing his parents beaming in the stands during his finest moments in pinstripes.

Incredibly, Jeter spent most of his time with the Gulf Coast Yankees batting under .200. But he gradually found his stroke and by the end of the season he was batting .202, with 10 doubles, three home runs, and 25 RBI in 47 games. After this harrowing start, Jeter looked forward to going home to Kalamazoo at the end of the season. But the Yankees had other ideas. They sent him to the Greensboro (N.C.) Hornets, a Class-A team in the South Atlantic League, to finish the season there. Only about 11 games remained, but the homesick Jeter wasn’t happy about it.

As it turned out, going to Greensboro was serendipitous. There he met Andy Pettitte and Jorge Posada, and, in a short time, formed a bond with them. The three players, along with Mariano Rivera, who joined the Hornets a year later, developed a friendship and support network that propelled the Core Four to the Bronx.

Jeter batted .243 in 11 games with the Hornets but made nine errors. Finally returning to Michigan in September, several events helped him get back on track. He took classes at the University of Michigan during the fall semester and lived on campus. “That period of time allowed me to get more acclimated to being away from home at a slower pace than I had when I went to Tampa.”

In addition, Jeter attended the Yankees spring training in 1993, “not because I did anything to deserve it, but because it was in my contract.” There he saw that players were not necessarily hitting the ball harder than he was, but they were more consistent. He learned that consistency is crucial to succeeding in the major leagues. “The opportunity to see what a Major League Baseball player looks like and how they carry themselves and how they work—I think that’s what flipped it for me.” With renewed vigor, Jeter returned to the Greensboro Hornets in 1993 and had a productive season, collecting 152 hits, including 11 triples. He had 71 RBI and stole an impressive 18 bases while hitting .295. Jeter experienced postseason for the first time in 1993, when Greensboro won the SAL North Division. It beat Fayetteville in the first round of the playoffs but lost in the championship to Savannah.

SAL managers named Jeter the league’s Most Outstanding Major League Prospect. But he had problems with the glove. By season’s end, the now-promising offensive player made a SAL record 56 errors at short in 128 games. That had the Yankees brass pondering whether Jeter was playing the right position.

Partway through the 1993 season, Jeter got a visit from Yankees general manager Gene “Stick” Michael. Michael had been a major league shortstop himself from 1966 to 1975, part of that time (1968–1974) with the Yankees. The GM noticed several things about Jeter’s fielding, including that he went after balls other shortstops wouldn’t dare to attempt to field, which impressed him.

Jeter said he remembers “Stick” telling him that, early in his own career, he went through three minor league seasons, starting in 1959, where he made 50-plus errors a season. Despite those error-filled minor league seasons, Michael developed into a slick-fielding shortstop in The Bigs. Michael didn’t give up on Jeter at short; in fact, he gave him some pointers and a plan.


After the Hornets’ season ended, the 19-year-old shortstop went to the Arizona Instructional League to work on his defense. That move paid off. In 1994, Jeter only made 25 errors. That season he started in Single-A before advancing to Double-A and then to Triple-A. He batted a combined .344 with the three clubs and had 186 hits with 50 stolen bases. He was honored as the Minor League Player of the Year by USA Today, Baseball America, and The Sporting News. But while Jeter was meeting with some success, he says he never lost sight of the fact that he “was still chasing the dream” and hadn’t reached his goal yet.

By the end of the 1994 season, the Core Four had all made it to the Triple-A Columbus Clippers. They’d all be with the Clippers in 1995, but they spent some time with the big club as well. Jeter got his call-up to The Show on May 28, 1995. He remembers getting a call in his hotel room from Clippers manager Bill Evers at around 6 a.m. “He said he would be right over, and I didn’t know what to think. I figured I got traded.” But to the 20-year-old’s surprise, Evers told him that Yankees shortstop Tony Fernandez got hurt and the Yankees needed him right away.

Jeter, who was batting .354 with Columbus at the time, hurriedly headed to Seattle, where the Yankees were to play the Mariners the next day. He called his parents, and Charles Jeter flew to Seattle. Jeter’s mom stayed in Kalamazoo to be with his sister, Sharlee, who had a softball game that day.

When Jeter entered the Yankees clubhouse in the Kingdome, he was stunned to see a road jersey hanging in his locker with the No. 2 on the back. He was well aware that single numbers were reserved for great players. Yankees lore has it that New York manager Buck Showalter thought Jeter should have the number because he was going to be great. Jeter’s more modest version is this: “I think it was the smallest jersey they had, and I needed a small jersey.”

On May 29, 1995, Jeter was in a Yankees starting lineup that featured Don Mattingly at first and Wade Boggs at third. Batting ninth, Jeter went 0 for 5 in his first game but bounced back the next day, going 2 for 3. Jeter ended up making only 13 starts with the Bronx Bombers that year. On June 11, 1995, he was sent back to Columbus with Mariano Rivera, who had been called up on May 16, 1995.

Showalter told both players that he had no doubts both would be back soon. “It was Mariano’s fault I was sent down. It’s true,” Jeter jokingly said about one of his best friends. “Mariano was a starter then and he had a bad game, so they sent us both down. We laugh about it now, but we were crying then.” Jeter only batted .234 in his short stay with the parent club. He knew he hadn’t earned his keep and continued to work hard.

By the end of the Clippers’ season in August 1995, Jeter was batting .317 with 154 hits, including 27 doubles and nine triples in 123 games. Jeter returned to the Yankees in September but saw little action. The Yankees were the AL Wild Card team in 1995. Though he didn’t make the postseason roster, Jeter was invited by Showalter to sit on the bench and watch. He saw the five-game AL Division Series in which the Yankees won the first two games before losing the next three and ending their season.

Jeter wasn’t sure what was going to happen in 1996. The team had a new manager—Joe Torre. Yankees owner George Steinbrenner believed the team was close to getting into the World Series and winning a championship but wasn’t sure the team would make it with a rookie shortstop. Torre let it be known in the spring of 1996 that Jeter was his choice for shortstop and the job was the 21-year-old’s to lose.

The sure-handed veteran, Tony Fernandez, loomed in the background. That made Jeter nervous, and at the start of spring training he played that way. Behind the scenes, the Yankees were looking for another veteran shortstop to either back up Fernandez or maybe start. One of the players the Yankees considered trading was Mariano Rivera, who hadn’t yet made his mark on the mound. The need for a shortstop seemed to become even more urgent when Fernandez broke his elbow toward the end of spring training. But Michael convinced Steinbrenner that he should give Jeter a chance. Michael was considered a great evaluator of talent, and he was also a top adviser to “The Boss.” Steinbrenner reluctantly agreed, and he wouldn’t be sorry.

Joe Torre always contends that Jeter won the shortstop job. When asked about it, Jeter said, “I got it by default. Tony Fernandez got hurt.”

The Yankees opened the 1996 season on April 2 in Cleveland, and Jeter answered any doubts on Day 1. The new Yankees shortstop led off the top of the fifth inning against veteran hurler Dennis Martinez and hit a home run. Then came what many remember as a classic moment for “that new kid at short.”

Cleveland was batting in the bottom of the seventh. With a runner at second, Indians shortstop Omar Vizquel lifted a short fly ball over the left side of the infield into no man’s land. Jeter took off after the ball and, with his back to home plate, made an over-the-shoulder, acrobatic catch. That was a welcome-to-pinstripes moment for Derek Jeter. There was no stopping him after that, as Jeter realized his lifelong dream. He was the everyday shortstop for the New York Yankees.

The Yankees went on to capture the AL pennant in 1996 and beat the Atlanta Braves in the World Series. That was due in no small part to their new shortstop, who was named Rookie of the Year with a .314 batting average, 183 hits—25 of which were doubles—and 78 RBI. The Yankees wound up winning five world championships (1996, 1998–2000, and 2009) during Jeter’s 20-year major league career (1995–2014).

“It’s hard to say which is your favorite world championship. You play to win a world championship, but the first time you do anything, it’s special. So I guess I’d have to say 1996 stands out. But I liked the one in 2000 as well because we were playing the Mets.” Jeter was the Most Valuable Player in the 2000 World Series.

“I really appreciated the 2009 world championship the most because we hadn’t won a title in nine years. When I first came up, we were winning World Series a lot, and then not to win one in so long, it means a lot to win it again, especially after all that time. So when you haven’t won for a while, you tend to really appreciate it when you do.”

Jeter was in the postseason 16 out of his 20 years with the Yankees. He played in 158 playoff games. In postseason, the Captain had 200 hits, which included 32 doubles and 20 homers, and a .308 batting average. He participated in 16 AL Division Series, 10 AL Championship Series, and seven World Series.

During the 2001 World Series against the Arizona Diamondbacks, Jeter earned the nickname Mr. November for some late-inning heroics in the fourth game of the series, hitting a home run in the bottom of the 10th inning at four minutes past midnight on Nov. 1 for a 4-3 victory. The scoreboard flashed “Mr. November.” The series was tied 2-2 and Jeter had a new nickname. The Yankees won Game 5, too, before losing twice in Phoenix as the D-Backs clinched the Series. But Jeter’s clutch home run is still considered a great moment in Yankees history.

Another unforgettable moment came earlier in the 2001 postseason, one that fans still talk about. Known simply as “The Flip,” it came in Game 3 of the 2001 American League Division Series against the Oakland A’s, and Jeter said he gets asked about the classic play all the time. A throw from right field missed two cut-off men, but Jeter, running toward the first-base line to back up the play, fielded the throw on the foul line and flipped it to catcher Posada, who tagged out Jeremy Giambi, preventing the tying run from scoring. The Yankees won the game, 1-0. That big play shifted the momentum from the A’s to the Yankees, who went on to win the ALDS three games to two.

“I’ve always said, since the play happened, that I was only doing my job. I was in the area where I was supposed to be. My job was to watch the runner. When I saw the ball going down the first-base line, my job was to see if there was a play at third and redirect the ball there. Fortunately, I saw that I had the opportunity to get the out at home plate. The play came at a good time because it helped us win the series. So, yes, I think it became a defining moment in my career.”

Miraculous plays became synonymous with Jeter throughout his career, and there were many, but the one that stands out most came on Sept. 25, 2014 in his last game at Yankee Stadium. Jeter got a game-winning single in the bottom of the ninth inning to give New York a 6–5 win over Baltimore.

“It’s a little unfair to pick that game because it’s the freshest in my mind. I’ve said it time and time again—how much respect and gratitude I have for the fan base in New York, the way they treated me, not just my final game but my entire career. It was great to have one last magical moment at Yankee Stadium.”

Jeter talking to the media in New York after being elected into the National Baseball Hall of Fame Class of 2020 on January 22. Photo: Mike Stobe/Getty Images

Jeter talking to the media in New York after being elected into the National Baseball Hall of Fame Class of 2020 on January 22. Photo: Mike Stobe/Getty Images

Jeter developed a special relationship with Steinbrenner. “The Boss was simple: Win. That was it.” Jeter thanked the Steinbrenner family for the opportunity to play his entire career in New York, saying “The thing I always wanted to be remembered for was being a Yankee.” Jeter also mentioned Torre, his manager for 12 years (1996–2007). “He’s probably the best communicator I’ve been around. He preached that you treat everyone fairly, treat everyone the same, and you have to take the time to get to know people. That’s a lesson I learned from him early on in my career.”

Jeter was also quick to thank all the people who helped him throughout his life and made the Baseball Hall of Fame possible, including his parents, his sister, and his wife. He is happy that his two little daughters are in his life to share the event with him. Jeter looks forward to reminiscing about his career with his children when they are old enough to understand it all. “Just the good stuff. Nothing bad, just strictly all the highlights.”

Jeter will take his career 3,465 hits, 1,311 RBI, 260 homers, and .310 batting average to Cooperstown, along with countless clutch plays and timely hits. His jump throw from deep in the hole at short or his triumph-raised fist after a key victory are as integral to Yankees tradition as Babe Ruth trotting around the bases after a home run.

For Jeter, part of the thrill of playing in New York was hearing his name announced by the late Bob Sheppard each time he came to bat. Sheppard was the Yankee Stadium PA announcer for over 56 years. So one can’t help but think that when Jeter is inducted into Cooperstown, and each time you gaze at his plaque, somewhere in the far-off recesses of your mind you will hear Sheppard saying, “Now in the Baseball Hall of Fame for the New York Yankees . . . Number 2 . . . Derek Jeter . . . Number 2.”

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