Newsletter 97: About That NY Mag Cover Story From March

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I’ve decided to start putting some of the best newsletter essays here on Medium, so more people can read them. You’re still better off just subscribing. This one is from March 2018, the liner notes of the big New York Magazine cover story I wrote back the spring. This was the biggest piece I wrote this year, and since it’s nearly the end of the year, I thought it might be worth looking back at. Happy holidays.

One of the biggest pieces I’ve ever worked on dropped this week, the cover story in New York magazine leading off their “How To Raise A Boy” feature. As you know, I write a lot, but nearly 4,000 words in a national magazine to write a personal essay is a rarity, to say the least. If you haven’t read the piece yet, here it is.

Anytime there’s a piece that long, there’s a backstory. So here are some liner notes to the piece.

We have been working on this for a loooooong time. My editor is David Wallace-Wells — perhaps best known for this staggering piece — and he originally approached me to write this as a long feature about “Raising Boys in the Age of Hillary.” That’s right: We started initially researching this piece back in September 2016. That was 18 months ago, but of course it was 40,000 years.

David Wallace-Wells is the best editor in the world. Ever notice how much better I sound in New York magazine than I do in the newsletter, or anywhere else? David Wallace-Wells is a magician. All editors are lifesavers. But he is the best lifesaver.

The reason this story took so long is that it initially tried to do too much. We have gone through so many permutations of this story, and the reason we did is that we originally attempted to answer every aspect of the idea of raising a boy in my piece, and my piece alone. I talked to a bunch of sociologists, I interviewed a bunch of parents, I read a ton of books about parenting boys, and we kept hitting brick walls because the topic was just too vast. At one point, it was almost entirely about Trump, which is understandable but also both too depressing and too unpredictable: Tying it to him guaranteed he’d do some other, different dumbass thing between the time we closed the story and the time it published. He had to be mentioned in it, but it ultimately veered as far from him as it could. And all the stuff I couldn’t answer — and there was a lot! — made up the rest of the package, with so many excellent pieces by so many excellent writers. (You really should pick up the issue on the newstands.) And even with that, the package can’t help but feel a little incomplete.

The online version is a lot longer. I know I told you to pick up the mag version, but know that the magazine version is roughly 1,200 words shorter.

Here’s an alternate lead, from a version dated more than a year ago:

One of my earliest political memories was my father telling me the world was going to end. It was early 1985, and I was nine years old, flipping through the TV Guide. There was a special that night on NBC called “An All-Star Tribute to Dutch,” in which various old Hollywood celebrities — Frank Sinatra, Dean Martin and Charlton Heston, primarily, though Emmanuel Lewis randomly shows up — were to perform at a birthday celebration for President Reagan. I liked “Webster,” so I asked my father if we could watch it.

My father, born and raised in the same rural Central Illinois town where he was raising his own children, was no bleeding heart liberal; he was a military man who made his son get a fresh crewcut every two weeks and drank regularly at the V.F.W. in town. But he was also a proud union man, a substation electrician for CIPS, the power company in the area. He not only loathed Reagan, but he was terrified of him. He legitimately considered Reagan’s hostility toward the USSR as posturing that might just get everybody killed. (This was two years after we had all watched the TV-movie “The Day After,” just like they all did in “The Americans.”) Dad scowled at my request, and then said something that I still remember vividly today.

“Yeah, you’ll be saying, ‘thanks, Dutch,” when the bombs are landing on your head,” he growled.

I decided I was OK with not watching “An All-Star Tribute to Dutch.” I don’t remember very much about the Reagan administration. But man, do I ever remember that.

I’m glad we didn’t go with that lede. I don’t even know where I was trying to go with that. EDITORS WILL SAVE YOUR LIFE, PEOPLE.

My wife had total veto power. I don’t write about my life much for publication anymore: I tend to limit that to this here newsletter. But something this personal, and about the single most important thing my wife and I have ever been a part of, required total buy-in. My wife is a lot smarter and a lot better reader than I am, and she had many suggestions/demands, every single one of which made it into the final cut.

She also is a quality dancer.

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We had to cut one of my favorite quotes. My friend Tim Kelly, who runs The Rook & Pawn here in town, said this about raising his kids in a Trump age.

“We’ve limited exposure to [Trump] at pretty much every level,” he says. “We don’t watch the news until [the boys] are in bed, I switch to music on the radio when they get in the car. There’s a window here where I think if we stay away from him and again just go back to teaching basic human decency, we may be able to make Trump nothing more than a weird, foggy memory from their childhood.”

I know a lot of parents who are doing this. I know we are.

The kid on the cover of the magazine is not either one of my sons. They are a lot cuter than that.

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It was a good cover, though!

Dad fact-checked the shotgun in the lede. He even had his brother get the gun out of his closet back in Illinois and take a picture.

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Unfortunately, we called it a “bullet” instead of a “round” in the first few paragraphs, which has allowed a few gun folks to have some (justified) fun at our expense. But that’s the gun!

I’m very pleased I got in the phrase “As you can surely tell having made it this far into this piece, I am not the world’s greatest writer.” Almost an old “Life As A Loser” throwback.

The piece purposely has no answers. But if you’ve got any: I’m all ears.

Subscribe to the newsletter right here.

Written by

Writer, New York, NYT, MLB, WaPo, others. Founder, Deadspin. Author of four books, with fifth, “How Lucky,” coming May 2021. https://williamfleitch.substack.com

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