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Bagging the Media Queen

From December 2008: For two years, Kitty Kelley, America’s most notorious celebrity biographer, has been tracking Oprah, a notoriously private subject. The multimillion-dollar game of cat-and-mouse promises to play out in an epic cultural showdown

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Kitty Kelley has Oprah in her sights

With Kelley now embarking on year 3 of her Winfrey project, I can offer the following bits of information from months of canvassing her sources (potential and actual): Kelley’s charm is irresistible—perhaps hazardously so, depending on your perspective—capable of prying voice from the mute. Her flattery—well formed and informed—can similarly misdirect and seduce. Even the stiffest of turned backs can slacken in her presence. Sources are more likely to open up if they have nothing negative to share; people without quality dish tend to divulge what they know happily and endlessly. It’s best never to underestimate Kelley’s reach—a maxim that’s equally true of her subject. “We do not provide any information or video about Oprah without her express permission,” I was told by a representative at the first television station where she worked. (Oprah’s official stance regarding the book, per the New York Daily News: “I’m not discouraging it or encouraging it.” And then, playfully: “And you know I can encourage!”) Still, the name Kitty Kelley can jolt—“Check this out—yikes. . . . ” blurted an e-mail from a good friend who had written about Oprah when forwarding me Kelley’s initial salvo seeking his input. But, then again, her reputation cuts multiple ways: A furniture maker in Oprah’s native Mississippi asked me, “How about e-mailing [Kelley] and plugging me a little bit? You know, that I’m an interesting character, and here’s my slant on what went on. If there’s any way that I could get my name in that book, it would be very big.”

Last summer, Kelley ventured to Oprah’s hometown of Kosciusko, Mississippi, population 7,372, 70 miles northeast of Jackson and 706 miles from Chicago. There, she walked the ceremonial, although unpaved, Oprah Winfrey Road and Buffalo Cemetery, the multigenerational resting place for Oprah’s maternal relatives. Kelley has also called upon family members. “I never did quite get Kitty’s intentions,” says Oprah’s cousin Katharine Carr Esters, her tone Southern-steely. “Part of the time, she sounded as if she was doing what I do—admiring my cousin. And at other times, it sounded like she was trying to get something ugly. I didn’t like that. She didn’t get any ugly from me.” Despite Kelley’s steadfast claims that she was writing a positive book—“So far, I don’t see anything negative on this woman,” she remarked to the Washington Post in late 2006—most everyone I spoke with remained leery of her intentions.

In Nashville, home of formative Oprah years (high school, college, nascent broadcasting days) and of Vernon Winfrey (father, beloved barber, former city councilman), locals imparted their eternally ripe and affectionate Oprah memories to Kelley unsolicited. “After I ran an item [about Kelley being in Nashville conducting interviews], people contacted me about wanting to get in touch with her,” says The Tennessean columnist Beverly Keel. “Many Nashvillians that knew and know Oprah are very proud of her and like to brag about her every chance they get. I remember her anchoring the news here when I was growing up. We think of her as our Oprah. There’s no dirt here. She’s the ultimate hometown girl does good.”

When in Chicago, Kelley has dined at RL, a frequent Oprah haunt, and visited the two major daily newspapers. Her task bemuses local media people, who know firsthand about Harpo’s sound-and-snark-proof walls. “Kelley’s got a tough job,” Michael Sneed cautioned in her Chicago Sun-Times column. “Oprah’s people are famous for clamming up.” Many people even declined to talk to me about declining to talk to Kitty Kelley. Indeed, to write about Oprah is to invite silence—rigid, constant, and unexplained. The common refrain I hear: “What does anyone have to gain from talking to Kitty Kelley about Oprah?” No one ever provides me with a compelling answer.

Thus, in Chicago, Kelley’s Winfrey quest is greeted with a pervasive hearty skepticism: “What are you doing in town?” the Chicago Tribune stalwart Rick Kogan asked when Kelley found him outside the Tribune Tower.

“I’m working on a book about Oprah,” she told him.

“Good fucking luck,” he said.

Kitty Encounter I—Neil Steinberg, Chicago Sun-Times columnist/author, gleeful Oprah cynic: She arrives via e-mail, press release officially announcing her business attached. Lamentably, she had missed him during a previous trip to the paper. Per wont, she knows his work, which she cites with admiration and chagrin, unable to find his irreverent, out-of-print 1996 catalog of aggravation, The Alphabet of Modern Annoyances—“O” being for Oprah, wherein he terms her a “frog-like dominatrix presiding over her Theater of Pain.” Steinberg responds immediately, full of his signature cheeky aplomb: “Dear Miss Kelley, I’m flattered that you’re interested in reading ‘O is for Oprah.’ I’ll drop it in the mail tomorrow—no purchase necessary. The pleasure of helping you with your important work is payment aplenty.” As further aid, he directs her to a couple of prominent Chicagoans with Oprah associations. Eventually, he sends her the galley of his recovery confessional, Drunkard; she happily provides a blurb for its jacket. He reads it to me over the phone, still marveling at its fulsome gush: “‘If you want to get drunk on words, not wine, and become intoxicated by real writing, read this fabulous book by Neil Steinberg. His journey into alcoholism and recovery soars above all other drinking books you’ve ever read. Drunkard is funny, sad, and illuminating, and leaves in its wake’—here’s the kicker—‘the macho drunkalogues of everyone from Ernest Hemingway to Pete Hamill.’ When she compares you to Hemingway!” Steinberg exults. He then demurs: “It was so flattering that I considered whether she was mocking me by excessive praise.”

Kitty Encounter II—Sugar Rautbord, author/socialite, Oprah Winfrey Show guest: “There were several unreturned phone calls, and then a friend asked if I would talk to her. I spoke with her for a few minutes. She wanted to meet with me when she was in Chicago, but since she already seemed to know everything I had written and said about Oprah, I didn’t see the purpose of it. Plus, I knew people who talked to her about Nancy Reagan and were devastated when they read that book. I also felt uncomfortable because I’m such an Oprah fan and a friend. When I hung up, I thought, ‘Wait a second—I’m probably going to be listed as a source or footnote because I took her call!’ I plead guilty to recommending the best place to eat in town with high visibility—RL. So it’s not like I told her to go to hell, I told her to go to RL.”

Illustration by Sean McCabe



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