Derek Jeter’s Greatest Hits

When New York Yankees shortstop Derek Jeter smacked his 3,000th career hit on July 9, it was the kind of picture-perfect moment kids dream of.

A warm summer day, a packed house and a home run ball caught by a lifelong Yankees fan who handed it back to Jeter with a huge smile. Only 27 other players in the history of professional baseball have managed the 3,000-hit threshold, and none had done it while playing for the Bronx Bombers.

But in the midst of all the celebration of Jeter’s momentous accomplishment, no one seemed to have given much thought to his failures—except Jeter himself. At a recent speech to a group of high-school student leaders in Tampa, Jeter offered them a little perspective. “Many people have celebrated that 3,000th hit,” Jeter said as the students erupted in applause. “But not as many people have thought about the number of times I failed in order to have 3,000 successes. I’ve had more than 6,600 times I’ve come up and not gotten a hit. In order to succeed, you have to be able to handle failure. That’s why those 3,000 hits mean so much to me. To me, they’re a sign that I handled the times when things didn’t work out. I hope that’s the lesson people get.

“People look at anyone successful—I’m not just talking about myself—but they think you just wake up and you’re in the NFL or Major League Baseball or have a published book. But there’s a lot of hard work, sacrifice and failure that goes along with it.”

The teenagers in the room went silent as they listened to their hero—just days removed from such a historic accomplishment—talking about the importance of failure along the road to victory. As Jeter wrapped up his session, the appreciation for his lesson was palpable. The young leaders seemed encouraged, empowered… and a little relieved.

And that’s exactly the point of the Turn 2 Foundation, the community outreach program that Jeter established early in his career and that his family—especially his younger sister Sharlee—helps to run.

As a child, Derek Jeter enjoyed the typical sandlot dreams about making tremendous plays in front of throngs of cheering fans, but long before he flirted with the record books, Jeter was working toward another goal, one that is even more worthy of celebration.

Sitting in a Detroit hotel room in 1996 and sharing a pizza with his dad, the 22-year-old rookie and Yankee phenom shared his dream of starting a foundation that would help equip kids to make the best possible choices for their lives and their futures. “I was a big Dave Winfield fan,” Jeter said when he sat down with SUCCESS after speaking to the students. But it wasn’t just the Baseball Hall of Famer’s career that Jeter admired as a kid. “He was one of the first big athletes to have a foundation. I always thought that was cool, and I wanted to be like Dave.”

So that night in Detroit, “I thought the time was right,” he recalled, and he and his father, a career drug counselor, sketched out the first plans for what was to become the Turn 2 Foundation.

With a mission “to create and support signature programs and activities that motivate young people to turn away from drugs and alcohol and ‘Turn 2’ healthy lifestyles,” the foundation provides leadership training, scholarships and personal-enrichment programs to children and teens, not only in Jeter’s old stomping ground of western Michigan, but also in his new hometown of New York and in the Tampa Bay area, where the Yankees have their spring training facilities and Jeter maintains his off-season home. The 2011 Jeter’s Leaders Leadership Conference in Tampa included students from each of those locations, as well as from New Orleans, a city Jeter has “adopted” in the wake of Hurricane Katrina.

“There are a whole lot of issues teens have to deal with that I didn’t have to deal with when I was younger, like texting while driving,” Jeter said. “Teens nowadays, with the peer pressure and things they have access to—I’m sort of happy I grew up a long time ago.”

Turn 2’s stated goal is “to see the children of these programs grow safely and successfully into adulthood and become the leaders of tomorrow”—and that’s no empty boast. To date, more than $12 million has been awarded in grants for healthy-living programs in the target cities, and thousands of children have benefited from the school programs, summer camps, baseball clinics and other activities that are all part of Jeter’s vision.

When asked what he was most proud of, given all the tremendous work his foundation has done, Jeter beamed and immediately answered that it was hearing from the students and their families following graduation. “I enjoy hearing personal stories—someone saying they just graduated or saying all the influence the program had on their lives. That’s what makes you feel good because you can’t impact everyone but when you hear the stories of the people you did impact, it makes you feel like what you’re doing is worthwhile.”

Nor is Turn 2’s goal one to which its founder only pays lip service. After 15 years as one of MLB’s biggest names and hottest talents—and the tabloids’ remorseless reports on his dating life—there hasn’t been a whiff of scandal surrounding him. Jeter’s name has never been linked with performance-enhancing drugs, nor does he have the rap sheet of arrests that many other celebrities and sports pros do. By coupling a responsible personal life with a headline-grabbing career, Jeter has proven, year after year, that it is possible to work hard, have fun and be a success, despite pressure to do otherwise.

In fact, it’s his tough-but-clean professional reputation that landed him in the No. 1 spot as baseball’s most marketable player for endorsement deals in a 2011 Nielsen survey. Jeter was rated as having the highest level of “sincerity, approachability, experience and influence” of any player currently in the league. It’s an image he’s worked hard to protect, hoping to show the kids in Turn 2 programs (and all of his fans) that it really is possible to have it all if you just resolve to make good decisions.

The irony, though, is that Jeter is not a fan of the concept of an athlete celebrating his or her public image. “You always hear the word ‘image,’ but I am who I am,” he explained. “I think a lot of times, people say ‘image,’ and that’s how they want people to view them. I don’t want people to view me any differently from who I am.

“I think a lot of people look at their role models and assume their role models are perfect,” Jeter continued. “But no one’s perfect. You have to be accountable for your actions. That’s first and foremost. You make mistakes, you learn from mistakes. You have to be honest about them. You can’t say one thing and do the complete opposite. You can learn from your mistakes; you can learn from other people’s mistakes. That’s what I’ve always tried to do.”

Jeter said he has high expectations for the Turn 2 Foundation every year, and it continues to exceed them.

“I’m not afraid to fail on the field,” he said. “But we’re not going to fail here.”