Now that my son plays baseball I’ve been reintroduced to the sport I’ve loved since I was a kid. As a die-hard Yankees fan, I’ve been fortunate to watch many amazing baseball players over the years, but the one I admire most is Derek Jeter. I even got to meet him once, and he was every bit as memorable in person as he is on the field.

Today Jeter will be honored at Yankee Stadium for his 20 extraordinary years on the team. I still can’t believe it’s been that long since he bounded onto the field like a puppy in pinstripes! Since then he has delivered moment after moment of unbridled baseball joy. When he announced he would retire at the end of this season, my first reaction was, “No way, the Yankees can’t go on without him!” But despite my own disappointment as a fan, I was very impressed with what he said: “I’m ready to start the second half of my life.”

Jeter says he’ll continue his philanthropic work and perhaps start a family. He has also expressed an interest in publishing—hey, maybe he’ll team up with Rewire Me! Whatever he sets his sights on, I’m confident he’ll be a great success. And the rest of us? I suppose baseball will go on without him, but for me it won’t be quite the same. Here’s what I’ll miss most about Derek Jeter:

His smile. Jeter always has a genuine smile for the fans, the batboys, the opposing players, and certainly his own teammates, either in congratulations for a brilliant play or consolation for a lousy one. He’ll dive headlong into the stands to make a catch and come up with the ball in his mitt and a big silly grin on his face (along with some scrapes and bruises). In all the years I’ve watched him play, I’ve never seen Jeter get angry. He gets the same bad calls that other players do, the same beanings by pitchers, the same taunts from opposing fans. But a stern look and shake of his head is the worst reaction I’ve ever seen from Jeter. No whining, no grudges, no blame game.

I still can’t believe it’s been 20 years since he bounded onto the field like a puppy in pinstripes! Since then he has delivered moment after moment of unbridled baseball joy.

Jeter might make what he does look easy, but it’s not. That high jumping catch and airborne flip to the relay man in a single, flowing motion? The clutch hit when you need it most? Stealing base in a nanosecond? We’ve come to expect it from Jeter, but his blend of grace and grit doesn’t come along often—in baseball or in life. Natural talent, yes, but honed by years of concentration and consistent hard work. Jeter’s fourth-grade teacher in Kalamazoo, Michigan recalls Derek announcing to his classmates that he was going to be shortstop for the New York Yankees when he grew up. And we talk about manifesting! How many of us start at age 9?

His growth. Remember when Jeter couldn’t help himself from swinging at the first pitch? (That puppy in him just wanted to go for anything!) But he learned to be patient, just as he learned to be a leader. As fans we have witnessed his transformation from irrepressible rookie to superstar shortstop to revered team captain—and what a ride it has been! If Jeter’s second act is anything like his first, the world is in for great things.

His respect. Longtime Yankees manager Joe Torre was always “Mr. Torre” to Jeter, and team owner George Steinbrenner was “Mr. Steinbrenner.” Never once has Jeter badmouthed team management or other players (despite having worked alongside some real corkers!). He doesn’t “kiss and tell” about women he dates, moan about bad press, or berate the paparazzi. Jeter’s a gentleman in a world of sports divas, and one can only hope his example inspires others.

Jeter’s fourth-grade teacher in Kalamazoo, Michigan recalls Derek announcing to his classmates that he was going to be shortstop for the New York Yankees when he grew up. And we talk about manifesting! How many of us start at age 9?

Sure, Jeter has made a ton of money playing baseball, and he certainly has enjoyed a more extravagant lifestyle than most of us ever will. But he also believes in sharing, especially when it comes to kids. In 1996 he created the Turn 2 Foundation , which raises and shares millions of dollars in the form of scholarships, grants, and leadership programs for high school students who commit to academic achievement, a lifestyle free of alcohol and substance abuse, and social change activism. The name was chosen, besides the baseball reference to a double play (and Jeter’s uniform number), to demonstrate the goal of giving youths a place to “turn to,” besides drugs and alcohol.

I’ll miss Derek Jeter on the field, but if he continues along this path—helping kids stay out of trouble and fulfilling their life potential—I’ll be cheering for him even louder than I have been in the stands. I’ll always remember him as a great ballplayer, but I look forward to seeing if he’s an even greater person. Go Derek!

Rose Caiola

Inspired. Rewired.