The Last Round

The Chicago Sun-Times columnist Neil Steinberg reveled in his role as a hard-drinking writer in the old mold. Then one awful night, his wife had to call the police

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Steinberg's heroes have always been alcoholic writers. Robert Benchley, James Thurber, Ernest Hemingway, F. Scott Fitzgerald. "You have to get it done," Steinberg says. "And the words work. That's the kind of writer I am. I don't know if it's a blessing or a curse, but I'm a facile writer. I like to write. It's the only time my anxiety goes away."

"Anxiety" is the word Steinberg uses to describe his urge to drink or his feeling that he just doesn't fit in. In one way or another, there has always been some kind of anxiety. He grew up in a suburb of Cleveland, Ohio, where his father, Robert, was a physicist, and his mother, June, was a homemaker. "But all the other Jewish families lived on the other side of town, so I was always the only Jew in my classrooms. I'd have to stand up every year and do my Hanukkah speech. 'This is a dreidel, and this is a menorah.' I hated it."  Before he went outside to play, he would arrange with his mother to call him back inside 20 minutes later so he could read. He liked words and their ability to bring order to things. They seemed friendlier than human beings. Even today, he says, "I don't know how to interact with people that well." Yet he was popular enough to be voted class president one year in high school. Attending Northwestern University, where he majored in journalism, he helped found a humor magazine and is still friendly today with several of those colleagues.

Over the decades, some family relations have, at times, become tremendously strained. In 1999, Steinberg tried to heal a lifelong rift with his father by sailing for a month and a half on a merchant-marine ship with him, sharing a small cabin from New York to Naples. He wrote about the voyage and their relationship in the book Don't Give Up the Ship. The trip did not go as Steinberg had hoped—the two failed to smooth over their many differences. In an article in this publication in May 2002, Steinberg's father was quoted as saying he had only "looked at the book."

"It was a flop because people want to read things like Tuesdays with Morrie," says Steinberg, "emotional treacle where everything works out in the end. And in my book, when we finally finished the trip, we were getting along worse than before." Steinberg has a sister, Debbie (as adults, they didn't speak for more than a decade), who lives in Plano, Texas, and a brother, Sam, who currently works in the Cook County treasurer's office. When Steinberg was released from jail, he temporarily moved into his brother's suburban basement.

He always believed that he would be a writer. The last job he had that didn't involve writing was when he worked in the kitchen at a Bob Evans restaurant in Berea, Ohio, when he was in high school. He was fired shortly after singing all the verses of "Ninety-nine Bottles of Beer on the Wall." After graduating from Northwestern, he briefly took a job in Los Angeles as a public-relations writer, then moved back to Chicago, where he freelanced and eventually took a job at the Barrington Courier-Review. Next he became an opinion-page editor at the Wheaton Daily Journal, but he was fired after writing a column that made fun of the publisher. He joined the Sun-Times in 1987.

By then he had been dating Edie Goldberg for about four years. They met when Steinberg wandered into an Evanston art gallery; she was working there part-time while attending Northeastern Illinois University. "I thought he was funny and interesting," she says, "so we went out to dinner." On their second date, though, Goldberg developed a migraine headache and went home early. "I think he felt I didn't like him, because I didn't hear from him for a year." When he finally got in touch, their relationship grew. Goldberg attended John Marshall Law School and worked as an attorney at Jenner & Block. But Steinberg resisted marriage until the end of a getaway weekend in Galena. "I was unloading this case of wine Edie had bought and I thought, Who is she going to drink this with?" he recalls. They married in 1990, and their first son, Ross, was born in 1995. (Their son Kent followed two years later.) Steinberg took an extended paternity leave, and Edie became a full-time mother.

In 1996, Nigel Wade, then the editor of the Sun-Times, persuaded Steinberg to come back to work by offering him a column that would run three days a week. Steinberg also secured a seat on the paper's editorial board, writing two to four unsigned editorials a week. (After his arrest, Steinberg was removed from the editorial board, but he was given a fourth weekly column.) At times, his column was humorous (the renovations to the Queen Anne house he bought in Northbrook), and sometimes it seemed deliberately provocative and even mean-spirited (the mocking of Native Americans for protesting certain images and team names). "He's rare in that the literary merit of what he writes is primary to him," says Robert Kurson, who worked at the Sun-Times with Steinberg for five years before moving to Chicago magazine and then going on to write books. "That is a hard thing to care about when you're working on a daily paper."

Steve Rhodes, a former Chicago senior editor and the founder of the blog The Beachwood Reporter, who has been a public critic of many of Steinberg's columns over the years, acknowledges that Steinberg is a talented writer. But, Rhodes adds, "I don't think the format of his column now—it's basically written like a blog—is suited to his strengths. And I think he has written some disastrously terrible columns about sports and politics over the years. But I've never had any personal animosity toward him. Neil has always shown a deep appreciation for newspapers and for newspaper culture."

Maybe that is part of the problem. From The Front Page to Network, journalists have always been cast—at least until these current politically correct days—as hardworking, hard-drinking characters. The University of Chicago sociologist Everett Hughes once wrote about "occupational mythology," the arrangements "by which men make their work tolerable, or even make it glorious to themselves and others." Traditionally in journalism, alcohol was part of the myth. "The journalist likes to think of himself as living close to the edge, whether he's covering real estate or Iraq," wrote Jack Shafer early this year in the "Press Box" column for the online magazine Slate. "If he drinks, he considers booze his muse. . . . Deny the journalist his self-image as a rule-bending individualist and you might as well replace him with a typist."

"I never had any problem getting my column done," says Steinberg. "Drinking never affected me." The only exception, he says, was the day of [Sun-Times veteran] Irv Kupcinet's funeral. "I remember going to Kup's funeral, and then a bunch of us went to Harry Caray's and got blasted. And then I wrote my column. When I picked up the paper the next day and read it, I had no memory whatsoever of having written it."

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This article appears in the June 2008 issue of Chicago Magazine.

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