Don Henley wrote nostalgically once about “The Boys of Summer.” A huge hit in 1984, years later Henley told Rolling Stone that the song represented a questioning the past and was about aging. A key line in the song that represents much of this sentiment and self-reflection: “Out on the road today, I saw a Deadhead sticker on a Cadillac. A little voice inside my head said don’t look back, you can never look back.”

It’s an ironic image for the 1980s: once counter-culture, fans of the Grateful Dead  driving around Cadillacs – a status symbol both of maturity and a touch of wealth. 

And whenever I hear it – and you still hear that song this time of year – I think of Derek Jeter. 

Didn’t expect that, did you?

For much of his career, I have held quiet and unassuming hatred for Derek Jeter. He represents the New York Yankees, and as a Boston Red Sox fan, he is the face of the arch-rival’s franchise. Therefore, if you are like me, you are just simply predisposed to disliking the guy.

At least that’s what I thought from 1995-2004. Then, on July 1, 2004, it became a genuine, sports hatred.
The Red Sox and Yankees – nearing the height of their rivalry, were battling tooth and nail in an extra innings game. With the score tied at 3 in the 12th inning, with runners at second and third and two outs, Sox outfielder Trot Nixon hits a pop-up down the third base line. Watching the game, you were certain the ball was heading foul into the stands.

Suddenly, there’s Jeter, screaming into the picture and making an over-the-shoulder catch. He is at the wall, so the force of his momentum launches him over the railing and into the stands. He makes the catch and cuts his chin, but the play ends the inning. Jeter leaves the game, but the Yankees win – and naturally, the announcers are drooling over him like the kid in that “Stacy’s Mom” video fawning over Rachel Hunter.

The announcers go on and on about what a leader “Jete” is, what a gamer, what a captain. It’s nauseating. It’s get-a-room-uncomfortable. It’s nails on a chalkboard to Red Sox fans. Remember, there were wounds still not healed from the previous October, so Sox fans hated everything Yankees even more so than normal. 

In hindsight, it was an amazing play. But I could never see it as such at the time. I was too young to appreciate it.

Fast-forward to the present.

Derek Jeter sits on the cusp of 3,000 hits and suddenly, I am nostalgic. 

After a contentious contract negotiation with the Yankees last winter, and with age becoming a factor, Jeter’s on the tail end of his career. And despite being a Yankee, I cannot help but feel sad that we’re losing something here. 

Jeter reminds you of the old boys of baseball. The Mantle’s, the Ryan’s – and some combination of both. He is a pretty tough cat, but he’s got this high amount of celebrity cache. The man has been with nearly every attractive celebrity female on the planet. 

Somehow, with all that happens in the current media age (Twitter, Facebook and 24/7 scrolling tickers) Jeter has managed to be in the public eye without anyone really knowing anything. It is like old Hollywood, really. People say they saw Jeter out doing this or that, hanging with this woman or that woman, but there’s no pictures, no proof – just stories. It’s mysterious, but not in a bad way since it leaves something to the imagination.

With Tiger Woods, once it all came out, there was literally nothing left to the imagination. In fact, your imagination died painfully as you scrubbed your eyes with Clorox. Either Jeter’s really, really good and doesn’t text people or he’s paid off everyone in Manhattan to keep quiet. And either way, that is pretty freakin’ cool.

Despite advancing in age and putting tons of miles on the tires with all the Yankees postseason runs, Jeter just went on the disabled list for the first time since 2003. He has really been a model of efficiency offensively and defensively. He is the only guy who could pull off forcing Alex Rodriguez to move to third base and then have people say that A-Rod was a better shortstop. And Jeter holds so many memories of iconic plays – mainly the flip play, where he tossed the ball to Jorge Posada to tag out Jason Giambi while running the opposite direction after cutting off a throw from right in 2001. 

I still don’t like Derek Jeter, yet I cannot help but feel odd (and old) that his time left in baseball is short.

We forget that athletes age too. Oh, we see it. We can see the gray hair and the loss of physique. We watch them stumble and get burned because they have lost a step – but we are not really comprehending it. At first, they get by on raw talent and athleticism. But in the end, it is all about being a cagey veteran who knows how a situation on the field or on the court will play out because they have been there, done that. 

This is where Jeter is at, like so many before him – getting by on what he knows and how the movie plays out. He has the script, he’s just executing the lines with more nuance. But the time is coming where he will not be able to get by on his wits anymore. 

And what does he do then? Naturally, he retires and becomes a manger or a TV analyst and becomes something entirely different. The better question is, what do we do next? 

It is always odd watching guys like Charles Barkley, Dan Marino and Troy Aikman in the studio or calling games. To anyone under the age of 30, that is all these guys are – old dudes referencing a game they once used to play. People view them with a sort of “Sure, I bet, old man” reverence, which is to say, “I hear you, but it’s just words.”

To anyone over 30, we remember how good these guys were. We were there, we saw their prime and we still hold them in high regard. 

And that difference in how people view athletes from one generation to the next is a striking similarity to Don Henley’s song and how we operate day-to-day in our own lives. It is why someone who enjoys Eminem does not get why people think NWA was controversial. It is why LeBron James can never be Michael Jordan. It is why I cannot begin to tell my kid how cool “Tecmo Bowl” was, because he has an X-Box and can run his own franchise, create himself as a player and set the price of popcorn in the concession stand. 

Perhaps that is why we can’t look back. We can never look back because only you understand the intrinsic value of what you’re looking back at if you were actually there to witness it.

In other words, for both Jeter and for me, getting older sucks.