Illustration by Kathryn Rathke
Illustration: Kathryn Rathke

When I was growing up in Woodstock, Illinois, I remember coming into Chicago and going to Wrigley Field. My father grew up on the North Shore and was a huge Cubs fan. In my little 5-year-old eyes, everything was gray and concrete on the outside, but then you’d walk up the steps and in and see the ivy-covered wall and the grass. It was like when The Wizard of Oz goes from black and white to color.

I came to Chicago from New York magazine in 1991 and immediately wanted to put in some changes. There was a lot of pushback from the staff. People grumbled about my efforts to make stories more urgent and compelling, with better details and quotes. And the Chicago Reader press critic did a story where I was basically portrayed as this slick New Yorker. When I told my former boss at New York about that, he said, “That’s funny. Out here, we always thought you were a hoople.”

I borrowed a story concept from Texas Monthly for how experts do things. One of our experts was the socialite and writer Sugar Rautbord. She had just written a novel that wasn’t quite X-rated. I decided to make “How to Write a Sex Scene” the cover. We got a wonderful photographer to shoot a naked woman sitting in a garden, typing. It was a beautiful black-and-white shot, more innocent than a Calvin Klein ad on the side of a bus. You couldn’t see anything. But half the newsstands wouldn’t put it out. It was, in my era, the worst-selling edition ever. I got at least a hundred letters from people complaining, including a woman who wrote, “We don’t allow any nudity in our house.” I should have written back: “How do you take a bath?”

When Donald Trump was opening his casino in northern Indiana, our managing editor, Shane Tritsch, toured it with him. All the qualities Trump has today were evident in Shane’s story: the lying, bragging, exaggeration, surrounding himself with yes men. When they were driving back to Chicago, Trump called me. He said, “You gotta put me on the cover.” I was perfectly nice to him and didn’t flat out say, “Are you out of your mind?” But I wasn’t about to put him on the cover. Because, as Shane made clear in the article, he was just bullshitting right and left.

Princess Diana was in town for two or three days in 1996, and the people of Chicago went bananas; everybody was trying to get close to her. We had a couple of writers who produced a fantastic story about a dinner at the Field Museum. It was the crowning event of her visit, and the tables were terribly expensive. This was in the days before Sue the Tyrannosaurus rex was there, and they had a big elephant. One of our writers, Ted Allen, was talking to a furious lady whose table was beneath the elephant. When he asked the event’s organizer about it, she said, “Look, somebody had to sit under the elephant.” And we all thought that was the funniest goddamn thing, so we put the line on the cover. I must have had 100 people come up to me and say, “What the hell was that about?”

One thing that completely blew past me: My wife and I used to go regularly to Second City in the ’90s. We’d come home and talk about how Steve Carell was the funniest guy we’d ever seen. And it just never occurred to me to assign a story.

I’ve said this to my Northwestern students a lot: Structure trumps language. So many of us have this idea that you have to be touched by a muse to write. But if you’ve got the facts, and you can put them together in a coherent, dramatic way, that’s how you tell a really great story.

With editing, you are aiming for clarity. My wife likes to say, “Every word has to fight for its life.”

I left Chicago on April 15, 2011 — literally the 20th anniversary of my arrival.