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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."
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