Pickett’s Charge

Debra Pickett trembles on the cusp of stardom. She knows it; her readers know it, colleagues at the Sun-Times know it–though none have called to complain she’s a callow princess unfit to mop the floors at midnight (which is the sort of thing I heard years ago when Richard Roeper trembled on the cusp of stardom). And of course everyone knows it across the street at the Tribune, a place that doesn’t want its own writers getting swelled heads.

The Tribune is strangely diffident about its columnists. They show up as little square faces in a sea of gray. “We know we’re supposed to have such people, so here they are,” says the design of the Tribune. “But our heart’s not in it.”

When the Tribune dropped Bob Greene, Crain’s Chicago Business did an inventory and noted an “icon” deficit at that paper: Greene, Royko, Siskel, Ann Landers–all of them gone. As it happened, Greene, Royko, and Ann Landers were Sun-Times imports; and as Siskel became famous on television he was cut down to size at the Tribune. It must be a great satisfaction to the editors to know that hundreds of thousands of people buy their paper every day even though there’s no one in it they want to read. Obviously they’re doing something right.

Writers drive the Sun-Times. Editors spot reporters who’ve shown the right stuff, give them a little extra space and a head shot, work up a design that says “pay attention,” and then wait for the readers to warm up. It’s “astounding” to Pickett how much mail she gets “from the regulars, from the people who buy the Sun-Times and have this relationship with it. I didn’t realize people have those kinds of relationships with their newspapers anymore, and they really do.”

“I think most of the Tribune columnists are blah, with the occasional exception of Kass,” says Michael Cooke, editor in chief of the Sun-Times. “When he’s not blah he’s often wrong, but that doesn’t matter with a columnist. If you think about the New York Times, the first words that come out of my mouth are Maureen Dowd and Paul Krugman. Thomas Friedman. I can’t think of the ones in the Tribune, except those two fools who write notes to each other.”

Those “fools” are Mary Schmich and Eric Zorn, each a writer I admire. (Schmich was offered a job by Cooke’s predecessor, Nigel Wade, and turned it down.) Cooke isn’t interested in whom I admire. “The words don’t come off the page,” he continues, establishing what’s wrong with the competition’s lineup. “They never ever color outside the lines. They don’t take risks. They’re not edgy. They’re corralled into typical Tribune safe journalism.”

A year ago Pickett started writing what she calls the “Sunday lunch thing.” In June she started showing up in Mark Brown’s page two space on Friday, and about that time a friend with an eye for talent and fast-trackers began to noodge me. He wanted to know when I intended to look into the phenomenon of Debra Pickett.

Occasionally there are writers who for whatever reason remind me of one of my heroes, a Canadian reporter named E. Kaye Fulton. I happened to be in Toronto in 1974 at the time of the city’s annual air show, and the Toronto Star gave Fulton the stock assignment in which the city room’s most delicate piece of porcelain climbs into a cockpit behind a stunt pilot, spends five minutes in the air, and dutifully describes how terrifying it was. Up to a point, Fulton’s report was routine. “I arrived at Toronto Island Airport with an empty stomach and a nervous grin,” she wrote. “I was too scared to move even my facial muscles for one last smile to the ground crew clustered on the runway.”

But Fulton didn’t climb into the cockpit. She had herself strapped to a vertical pole on the upper wing of an ancient Chipmunk biplane, where she flew upside down past an astonished editor sipping a martini in a rooftop restaurant in the harbor.

To pull a stunt like that takes more than courage. You must be willing to risk life and limb for the absurd. It helps to be young, and Fulton was 23. I’ve always sensed that Schmich would have been capable of something as foolhardy, and though she’s paid to be a lady who lunches I told Pickett I had the same feeling about her.

“I suspect you might be right,” she says. “Debra would bolt herself to the space shuttle,” says Cooke.

Pickett, who’s 29, grew up in and around New York City and was an English major at the University of Pennsylvania. “I always knew I was going to write, at least on the side, but I decided fairly early on that I didn’t think I could make a living writing–not the living I wanted to make. So because I didn’t want to be poor I found consulting. It was really hard, really challenging work, and it appealed to my competitive nature to see if I could do that. And I did it for five years.”

The tricky thing about consulting is that clients who know more about a subject–in her case, software–than you do hire you for your expertise. “It becomes kind of a confidence game,” she allows. “You have a little bit of knowledge and you build knowledge with every project you work on. So much of it is about whether you have your clients’ confidence and whether they’re willing to listen to you and accept you as an expert.”

If they do, you are?

“Right. If you’re five feet tall and look 15, it becomes how much talking can you do and how much working can you do to be an expert.”

And so from consulting–where success is measured by the ability to sound like you know what you’re talking about–Pickett made the vast leap into journalism.

“It was a remarkably smooth transition, really.”

Her work brought her to Chicago five years ago. A freelance piece she wrote for Chicago magazine with the regrettable title “Confessions of a Single Girl” was spotted by a consultant hired by the Sun-Times two years ago to create Next magazine. Next was a fiasco–a lifestyle supplement no one would advertise in that lasted six months. But Next launched Pickett. She joined its staff and survived at the Sun-Times after Next folded. “It was just about the end of the dot-com boom about to be bust,” she says, “and I’d put in enough 80- and 90-hour weeks and satisfied my longing to prove exactly how smart I was. I wanted to do something that–I would love.”

If everything breaks right for you, and you’re famous and syndicated and great papers duel for your services, will you ever make as much money as you made as a consultant? She thought about that. “I suppose there’s the potential to get close,” she said.

Cooke and vice president for editorial John Cruickshank suggested Pickett start taking people to lunch. The idea had worked before–a Toronto writer Cooke and Cruickshank knew of named Jan Wong had turned her stories into a book–and Pickett made it work again. “I have a tolerance for silence that’s 10 or 15 seconds longer than the other person’s,” she explains. “They start talking to fill it.” Her lunches, carried in the Sunday paper, were a low-pressure chance to make a name for herself–“We don’t have that many readers on Sunday,” she’s noticed–but before long readers started to respond to her way of plucking the wings off flies. The recent Jamie-Lynn Sigler lunch was memorable: “She was a very nice person, very sincere,” says Pickett of the actress who plays Meadow Soprano, “but everybody’s had those experiences where you’re sitting with someone and you think this person is so misguided I want to take her skinny little shoulders and shake her. And when you write about the person you have an opportunity to do that.”

Contrary to what Cooke seems to think, the Tribune carries several columnists worth reading. Without trying to be inclusive, Schmich, Kass, Zorn, David Greising, Rick Morrissey, and Barbara Brotman all repay the effort to find them and the plodding chore of reading them in the austere, skinny spaces most of them are given, an exercise not quite as severe as doing research on microfiche.

If history repeats itself, the Tribune will hire Pickett away when she’s past her prime–when she’s ready to trade the fun she’s having for stock options and job security. That moment isn’t now. “It’s funny,” she says. “Not being a Chicagoan, I guess I didn’t have a lot of the history, and so reading the columnists just literally for what they wrote, and not having a background in who was supposed to be who, I always found–and well before I started working there–I found the Sun-Times to have so much more compelling writing coming out of their columnists.

“One of the things that’s been really emphasized to me is how important it is to get out, to be in the city and be in the world, and be writing about things that are happening, things that are out there. I have the feeling when I read some of the Tribune columnists that they’re at home in their bathrobes and have just turned on their computers. I feel we’re a little more active in what we do.”

The View From Across the Street

Michael Cooke’s comments on Tribune columnists weren’t going to be allowed to pass without comment. I sent them, as well as Pickett’s, to Eric Zorn, Mary Schmich, and editor Ann Marie Lipinski.

“I have a lot of respect for the work of most of the columnists at the Sun-Times, who are generally class acts,” Zorn E-mailed me in reply, “and I don’t feel the need to trade self-serving barbs with Michael Cooke, Debra Pickett or anyone else over there. They’re not the ones I’d consult for an objective critique of our lineup, our writing and reporting, our accomplishments or even our coloring ability.”

Schmich told me: “Every time I hear people engaging in the interminable entertainment of columnist-bashing, I always think an essential thing is being overlooked: There’s more than one way to write a column. The people who fret over the decline of column-writing (generally people who’ve never written a column, or columnists who don’t include themselves) seem to believe there’s only one column model. In that model, argument, offense and biliousness are the columnist’s chief tools. There are certain columnists, and the people who love them, who don’t care if they’re wrong as long as they’re ‘edgy’ and ‘provocative.’ Insult passes for opinion, bitchiness for cleverness, attitude for intelligence. Makes my skin crawl.

“On the getting out and about question: For the first couple of years I wrote my column, I was out and about all the time. It’s a good place to be. What I’ve come to realize is that merely being out and about doesn’t make a good column. Taking someone to lunch on your expense account and writing up the conversation ain’t necessarily better than mulling over some quirk of human nature. Readers respond as strongly, if not more, to columns that don’t involve being out and about. A good columnist has a mix. By the way, I never sit at home writing in my bathrobe. I prefer my merry widow bustier.”

And Lipinski replied, “I don’t see that columnists matter more to the Sun-Times, it’s just that everything else matters less. The papers aren’t comparable. In putting the Tribune together every day we’re choosing not only from our columnists but from the work of a robust investigative team, a dozen foreign bureaus, a network of national and Washington correspondents, full coverage of Chicago and suburban news and a complete portfolio of arts and features coverage. The Sun-Times has virtually none of this. Our columnists are featured prominently throughout the paper and generate some of the most passionate readership we have. But unlike their tabloid counterparts, they’re standing tall with a lot of other great journalism, which is one reason so many of the Sun-Times’ best folks have walked this way.

“As for Mr. Cooke’s claim that it doesn’t matter if a columnist is wrong: Huh?”

In Loving Memory of a Real SOB

When Walter Annenberg died last week at the age of 94, the papers had two ways to go. America’s dailies favored a respectful send-off; their eulogies focused on Annenberg as a significant national figure of another era, a powerful publisher who’d been Richard Nixon’s ambassador to Great Britain and who did great good as a philanthropist. The alternative was captured by Jack Shafer in Slate: “Walter Annenberg was born of a congenital criminal, a rascal who never saw a business proposition that he couldn’t improve with a bit of violence,” wrote Shafer, who suggested the headline “Billionaire Son of Mobster, Enemy of Journalism, and Nixon Toady Exits for Hell” fit the occasion nicely.

The Sun-Times obit ran on page six, the Tribune’s back on page nine of the Metro section. These extremely different choices were logical on their own terms, for although both papers solemnly doffed their fedoras, only the Sun-Times said farewell to someone connected to Chicago. The Sun-Times obit, written by reporter Andrew Herrmann, noted that Annenberg’s

father, Moe, had been “a veteran of early 20th century Chicago newspaper wars fought with busted skulls and bloody knuckles,” and that Walter Annenberg had given $45 million to Northwestern University, whose school of education and social policy carries his name, and (just seven years ago) $50 million to the Chicago Public Schools. The Tribune, which merely picked up and greatly condensed the New York Times obit, offered none of this local detail.

The Tribune has a knack for shorting the Chicago angle of distant stories. Two months ago it carried a Reuters piece out of Greece about a controversial proposal to carve a 255-foot head of Alexander the Great into the side of a mountain. The author of this wild plan is the Chicago sculptor Anastasios Papadopoulos, who’s been raising money from the city’s Greek community. The Tribune didn’t add this helpful information to the Reuters piece even though the Reader and the Tribune’s own Rick Kogan had written about Papadopoulos earlier.

The Tribune’s Annenberg obit was of a different order of neglect. Who’d have thought from reading it that Moe Annenberg ever set foot in Chicago? Actually, he grew up here, and in the first years of the 20th century, he and his brother Max were thugs in the service of the circulation department of the Tribune itself. Hearst hired them away, and Max became circulation manager of the American as a newspaper war broke out. As Richard Norton Smith recalls in The Colonel, a biography of editor and publisher Robert McCormick, “Burly sluggers recruited by Max Annenberg intimidated newsstand dealers. Protesting carriers were beaten to a pulp.” The Tribune responded by hiring Max back, and the war continued. Moe stayed with Hearst, left Chicago to get out from under his older brother’s shadow, bought the Racing Form, became a millionaire, and near the end of his life served three years in prison for tax evasion.

The Annenberg name is inseparable from the history of the Tribune. But you couldn’t tell that from the Tribune when the Annenberg who made the family name respectable died.

News Bite

Jim Hoge was the Sun-Times editor who authorized the 1977-’78 Mirage project, which I wrote about last week. Today he’s the editor of Foreign Affairs. I’d E-mailed Hoge asking if he had any second thoughts about the ethics of the Mirage, but his reply arrived too late to appear in the column. Here it is:

“I thought at the time and have ever since that the Mirage project was an exemplary example of dramatic investigative journalism that made a difference. The Sun-Times resort to undercover work came only after traditional reporting efforts failed to sufficiently surface the relevant corruptions and their tie-ins.

“The key question concerning the propriety of the project was whether it involved entrapment. In preparation for the Mirage project, the reporters involved were instructed by lawyers in how to avoid entrapping suspects. Under Pam [Zekman]’s superb direction, I don’t believe the reporting ever crossed that ethical line.

“The question of entrapment first arose during Pulitzer Board deliberations. I am told it was a key reason that the Mirage didn’t win for investigative reporting. In the covering letter to the submission, we had explained the steps taken to avoid entrapment, apparently to no avail. I think the Sun-Times, its editors and reporters who were involved ought to be forever proud of the Mirage project.”

Art accompanying story in printed newspaper (not available in this archive): photo/Robert Drea.