O.K., I’ll admit it: I have way more free time than I know what to do with these days. And I can tell that you’re a nice guy, just from our handshakes. So I feel obligated to let you know that you’re doing this retirement thing all wrong. As someone who understands how to orchestrate an epic farewell, I’m here to help you out.
Don’t announce your retirement campaign too early.
Not many people know this about me, but when I first started playing baseball, I used to swing early and fast. Then my Little League coach pulled me aside—I’ll never forget this—and said to me, “Timing is everything.”
Now I’m sharing this very important sports metaphor with you—just because everyone knows that your retirement is inevitable doesn’t mean that you should publicize it more than two years in advance. I understand that it’s hard. There were times, back in 2012, when we were playing the Toronto Blue Jays and I was like, “Why am I even here?” I’ve been watching your press appearances, and I’ve got bad news for you, buddy: your face makes it look like you’re playing the Toronto Blue Jays every day. The key is to appear engaged, at least until you’re a year out.
Forget the people who don’t have your back.
If I could get rid of A-Rod, you can get some new Secret Service agents.
Stop walking around everywhere unannounced.
I get it. It’s fun to head over to Starbucks or Shake Shack just to see how everyone reacts. When I walk outside, grown men weep and babies high-five me. When you do it, you cause massive traffic delays and give CNN fourteen hours of news. But what’s really offensive about your surprise strolls is that you’re not even making the most of these opportunities. When I go on a spontaneous walk, I always make sure to bring along the proper equipment: a Gatorade camera crew, some guy who takes care of all that nostalgic black-and-white filter stuff, and a car that blasts Sinatra. My publicist calls these Moments™, and you’re wasting them.
When all else fails, tune everything out.
People always used to ask me, “Derek, how do you stay focussed? Derek, how did you hit that home run with everyone screaming at you?” I know that you have a lot on your mind—Syria, Ebola, ISIS, Ferguson, Ukraine, immigration reform, Republicans who want nothing to do with you, Democrats who want nothing to do with you, Malia going to prom, “Gone Girl” the film vs. “Gone Girl” the book, Putin, the economy, Biden surpassing you in popularity on Tumblr—but if I’ve learned anything from being in countless high-stress situations, it’s that there’s no problem that can’t be solved by eating a P. B. & J., stretching, and tuning it all out.
Incorporate your number into a word or phrase that will define your legacy.
“RE2PECT” was wildly successful. You could try “H44LTH CARE,” “BE44ER THAN ROMNEY,” or “INHERITED A SHI44Y SITUATION.”
Days before your final farewell, invite the media to your house.
People love to say that we’re unknowable, but I’ve learned that you can change this perception with a quick “Look at my home!” interview. I did this with my townhouse, in the West Village, and I’ve never even slept there. You’d be surprised, but showing people your bathroom is the best way to say everything while saying essentially nothing at all. Suggest headlines that include phrases like “As You’ve Never Seen Him Before,” or “Opens Up . . . Finally!” This will help convince everyone that privacy came with the job description and is not, in fact, a deep-seated part of your personality.
Celebrate your retirement for so long that even your enemies forget they hate you.
Steinbrenner taught me that the best way to make an impact is to force your enemies to tolerate you. It wasn’t an accident that I played my final games at Fenway—I wanted to make everyone in Boston sit through my career highlights one last time. When you retire, your goal should be to have Fox News air an hour-long highlight reel with that sad Enya song playing in the background. Boehner should be photographed with a solitary tear running down his face.
In closing…
From the Captain to the Commander in Chief, take my advice: don’t feel too sorry for yourself. You’ve been in the public eye for about a decade, but I’ve been dealing with this for 2wice as long.