The bombshell landed in December 2006 with language understated and almost coy: “Kitty Kelley, #1 bestselling investigative author, to write an Oprah Winfrey biography,” declared the press release, in smallish block letters, from the Crown Publishing Group. But in the days and weeks afterward, snickering media outlets throughout the world provided a more candid assessment of the announcement’s true implications. “It takes a lot to make Oprah Winfrey tremble, but even the chat-show queen and cultural icon must be quaking in her Manolos at the news that she is in the sights of Kitty Kelley, the poison pen biographer,” The Times of London posited. “In wake of Kitty Kelley bio deal, Oprah to start actively discouraging literacy,” joked the New York media blog Gawker. In Nigeria, the news translated quite simply to “Oprah Gets ‘Vicious’ Biographer.”
Most certainly, this book by that author could not make her happy—and that, in turn, could haunt Crown and its parent company, the sprawling Random House/ Bertelsmann media empire. After all, Oprah is widely considered the Midas of today’s publishing industry, her namesake book club serving as a fiscal supernova, causing a frenzied dash to bookstores whenever she recommends a new title or author. “There is a concern that a Kitty Kelley–style takedown of Oprah is not going to do any good for the corporation,” an executive at another Random House imprint told Crain’s New York Business. GalleyCat, a publishing-industry blog, reported that the book proposal had languished for months before Crown decided to buy it, with other publishers apparently unwilling to risk upsetting the empress of American daytime television and pop literacy. (Crown did not respond to requests for comment.)
But now enter the five-foot three-inch, 66-year-old Kitty Kelley, her work representing the sharpest scalpel in the messy genre of celebrity vivisection. Famously, she is more of a pejorative than an actual person. For instance, here’s a sampling of recent Google News alerts for her name: “The paper was guilty of ‘Kitty Kelley journalism’”; “He comes off seeming something like the Kitty Kelley of the history world”; and “An author might be tempted to pull a Kitty Kelley.”
To “pull a Kitty Kelley” apparently means to abide by the lowest journalistic standards possible and to focus heavily on gossip, innuendo, and scandal. Her critics allege that in her 30 years as a biographer, Kelley has offered little beyond scurrilous, secondhand details and anecdotes that portray her subjects as one-dimensional frauds or scoundrels. From her home base of Washington, D.C., she has written a total of six such biographies—all unauthorized, all about iconic figures or families, and all bestsellers many times over. And since, like Oprah, she, too, can sell books in impressive numbers, her advances are normally of the seven-figure variety. (Terms of the Oprah deal had not been revealed as of this writing, but “Oprah is a multimillion-dollar subject,” Kelley told the Washington Post.)
Typically, her books feature a particularly salacious tidbit—usually vehemently disputed by sources and commentators alike—that garners significant press attention and immense public curiosity: Jacqueline Kennedy Onassis underwent electroshock treatments for depression (Jackie Oh! 1978); Frank Sinatra committed a litany of unspeakable misogynistic acts (His Way, 1986); Nancy Reagan and Sinatra partook in lunchtime trysts at the White House (Nancy Reagan: The Unauthorized Biography, 1991); the insatiable Queen Elizabeth leaves Prince Philip with perpetually weary loins (The Royals, 1997); George W. Bush allegedly used cocaine at Camp David during his father’s presidency (The Family, 2004).
Her reporting process is exhaustive, consisting of hundreds of interviews and volumes of meticulously cataloged bio-graphical minutiae. She legendarily kept a file for each month of Sinatra’s life. As a result, Kelley produces weighty tomes—literally: The paperback version of The Family consists of 737 pages and the hardcover checks in at two pounds—that are footnoted with an academic’s zeal and often include detailed genealogical breakdowns. Universally, her subjects never dig her digging—or skullduggery, as they see it. “I hope she gets hit by a truck,” Nancy Sinatra Jr. said after the release of His Way.
Kelley’s modus operandi for the Oprah project promises to be equally thorough. “As she does with all of her nonfiction, Ms. Kelley plans to interview hundreds of sources, many of whom have never before spoken on the record about her subject,” the Crown press release boasted. Indeed, in the nearly two years since Kelley signed the deal, she has traveled back and forth between her office in Washington and Harpo’s Chicago nerve center at the corner of Washington and Aberdeen—and all Winfrey-relevant points in between—approaching anyone with any kind of an Oprah connection.
But in Oprah, Kelley has taken on a famously guarded and private target. Insiderly details on Winfrey are long forbidden by contractually enforced omerta—Harpo employees (now hundreds strong) are barred forever from speaking of what they have done and seen while working for her. And fierce Oprah loyalists include millions of devoted viewers, eager advertisers, highly compensated corporate partners, fawning celebrity guests-cum-friends, and, most recently, one eminently grateful Democratic presidential candidate. Oprah herself is loath to share her private business with the world on any terms but her own— The Oprah Winfrey Show serving as her confessional—meaning it’s best for any confidant who wants to remain close to keep mum.
The project seemed to invite an epic cultural standoff, a spectacle to behold. So I asked Kelley via e-mail if I could tag along, observing as she tried to puncture the unwavering fealty to Oprah. Politely, Kelley declined, explaining, “So far I haven’t encountered the dire roadblocks you’ve enumerated.” When I asked again later, she termed the book merely “a work in progress” and, therefore, somehow uninteresting. Yet it’s exactly her pursuit that’s fascinating. For decades, people have noted that nothing is more terrifying than opening your door and finding the 60 Minutes muckraker Mike Wallace waiting outside. But what does it feel like when Kitty Kelley comes calling to extract personal details about arguably the world’s most powerful woman? I set forth to find out.
Photography: (From Left) Nancy Kaszerman/Zuma/Corbis; Arnaldo Magnani/Getty Images
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
Kelley lives and breathes—air, not fire—in Washington, D.C., ensconced with her second husband in their fabled Georgetown home. They married in their garden, among 300 guests, a topiary dancing bear, magnolia tree, smokehouse, and the buried remains of her pet cats. Both of her postnuptial works (The Royals and The Family) are dedicated to him—Jonathan Zucker, allergist, the man “who makes dreams come true.” (Kelley on romance, according to the Washington Post: “Tulips from Mr. Right are far more romantic than a trip to the South Seas with Mr. Wrong.”) Although the late Supreme Court justice William Brennan, a previous occupant of the premises, once penned his decisions from a card table there, the place is now known in Washington as the “Kitty Kelley House.” “It makes me feel safe living here because of whose home it was before,” she remarked in the tony coffee-table book Private Washington: Residences in the Nation’s Capital. It is the house that Jackie Oh! bought and Nancy Reagan renovated. Much tittering ensues when the “Celebrity Georgetown Walking Tour” stops out front. Tour fun fact: Kelley’s vanity license plate reads “M-E-O-W.” She can be whimsical and self-effacing like that. Per The New York Times, “Around and above the toilet in the first-floor half-bath . . . hang framed cartoons, magazine covers, and newspaper front pages that recall the public figures Ms. Kelley has clawed, the hisses of protests she provoked, the catfights that ensued.” She entertains eagerly. “She threw me a fabulous, old-fashioned ladies’ luncheon when I happened to be in D.C. well after I had moved to Chicago,” says Ellen Warren, a Chicago Tribune senior correspondent and a longtime friend.
Unless she’s promoting a book, she discourages peeks into her own personal life. In the 1991 unauthorized bio-thrashing of her life, Poison Pen, by George Carpozi Jr., we learn that she helped the famed Washington Post editor Ben Bradlee prepare the Pentagon Papers for publication as a researcher for the newspaper’s editorial page, and that she wields her feminine wiles with abandon. Other biographical tidbits from various sources: Two of her favorite mottoes: “Speak the truth but ride a fast horse” and “Never explain—it tires your friends, and your enemies won’t believe you.” She suggested to TV Guide that the cartoon baby Maggie Simpson’s first words be “Hail Hillary!”—as in the former First Lady, current Democratic New York senator, and, in Kelley’s estimation, “one of the most fascinating women of the twentieth century.” When she first moved to Washington, she worked as a press assistant in the then Minnesota Democratic senator Eugene McCarthy’s office; in 2001, she held an 85th-birthday party for him at her home. She wrote in the girl-power anthology What I Know Now: Letters to My Younger Self that she considered The Family “political but not partisan.” She has spent an hour with Nelson Mandela and cohosted a fundraiser for Al Franken; she originates from the same hometown as Bing Crosby—Spokane, Washington, the “Lilac City,” where she was crowned teenage “Lilac Princess.” She attended the University of Washington.
Kelley met Oprah once, in the late 1970s, on the Baltimore morning show People Are Talking. The station assured me that a tape of their encounter did not exist. Kelley shot a pilot for her own daytime talk show in 1992. It featured an hour with Michael Jackson’s father, Joe—with exclusive footage from the Jackson family’s Encino home. “The main objective of the show was the same as Kelley’s books, which was to deliver the goods,” says Ron Ziskin, the pilot’s executive producer. He adds, “Kitty had a fun side to her, and she was able to be herself onscreen, which is unusual to have talent bring that to the air.” In this regard, she reminded him of that affable talk show madman Regis Philbin. Ultimately, though, Kitty Kelley never aired. “Only 28 markets (a mere 30 percent of the country) had bought Kelley’s offering,” Entertainment Weekly reported at the time, “so syndicator MCA pulled the plug.”
On the Chicago front, she frequently traded faxes with Esther “Eppie” Lederer, a.k.a. Ann Landers, who threw Kelley a book party for The Royals at her posh Lake Shore Drive digs; Kelley gave a gift from Hermès as thanks. “I’m sure Mother, like I, felt like a journalist girlfriend of hers,” says Eppie’s daughter, Margo Howard. “We’re all doing stuff at different levels, but in the journalistic community of women, there’s a sisterhood, and you meet people who you especially click with.” Whenever Kelley is in town—a younger sister lives in suburban Glenview, her husband the former CFO of Abbott Laboratories—she makes friends easily. “We both belong to the International Women’s Forum,” says Judy Wise, senior director of Facing History and Ourselves, a charity that educates students about global awareness. “It held its [October 2007] conference in Chicago, and she was randomly assigned to a dinner at my home. I found her incredibly easy to talk to, fun, interested in other people, and charming.” Adds Warren, “Kitty is Exhibit A for a great girlfriend. She is loyal, thoughtful, there for you. Just reading her books, you can tell she’s a terrific raconteur and a blast-and-a-half to be around.”
Kitty (Near) Encounter III—Paul Natkin, former staff photographer of The Oprah Winfrey Show: She prowls Lake View, looking for his house. He has either not answered or declined her earlier overtures. “I look at her as the paparazzi of writers,” he explains. But on a Thursday in late June, she swings by unexpectedly—a bold move that might entice him to talk. She’s particularly interested in his Oprah photographs. He maintains a library of about 30,000 of them. Famously, he sued Oprah to retain their copyright; they later settled out of court. But he isn’t home when Kelley shows up. Hastily, she writes him a short note asking if they might be able to meet and slips it into his mail slot. “I still wonder what I would have done if I had been home,” he says. Again, he ignores her appeal for an audience. He says he did keep the note for possible framing: “To be stalked by Kitty Kelley is a pretty cool thing.”
People who understand the Harpo fortress of silence give Kelley varying odds at piercing its hush. “Whatever Oprah does to her cringing underlings, she must cut out their tongue with a hot iron, because you never, ever hear them dishing dirt,” says Steinberg. “So one of two things: Either they will line up to anonymously find an empty spot on her back to stick the shiv in; or, and this is my bet, they’re so inculcated with fear that Kitty will come up with a dry well.” Bill Zwecker, his colleague at the Sun-Times, agrees: “There will be some naysayers here and there,” he says. “But Oprah has made a commitment to Chicago. She could have left this town many times for Los Angeles or New York. But she’s remained in Chicago. We’ve been her good-luck charm, and she’s been our good-luck charm. That’s why people here have a sense of loyalty to her.”
Natkin, who no longer speaks to anyone at Harpo, clarifies the unshakable pillar of this allegiance. “I used to hang out with the producers and directors of The Oprah Winfrey Show. They all had beautiful homes in the suburbs, sent their kids to great schools, and had a shelf full of Emmys in their living rooms. But I always thought that they were completely trapped. Unless they uprooted their lives and moved to Los Angeles or New York, they would never get another job like that in television. So it’s not really loyalty, it’s necessity.”
Conversely, Ann Gerber, gossip doyenne for the Gold Coast newspaper Skyline, speculates, “There have got to be people out there who haven’t signed confidentiality agreements. So I would think Kitty could find people. There are lots of people with loose lips.” And Ellen Warren, confident of Kelley’s abilities, offers, “Hello? Remember Frank Sinatra?”
Kitty Encounter IV (serving perhaps as the perfect paradigm of the Kelley quan-dary)—Chris Clark, the legendary Nashville anchorman, an early Oprah mentor: She goes to him, traveling from Washington to Nashville. They meet at his office on the Middle Tennessee State University campus, where he teaches broadcast journalism. In Nashville, he is Bill Kurtis, Floyd Kalber, and Fahey Flynn rolled into one. He retired from the local CBS affiliate last year after more than four decades of anchoring the nightly news; Oprah sent him a sweet video tribute to mark the occasion—“I thank you for giving me my first break in television when breaks were really hard to find.”
He hired her when she was just 19 years old, making her Nashville’s youngest and only African American television personality. Despite her age and inexperience, she told him that she could operate a camera, write news copy, and report stories. She could not. It didn’t matter. “Those things you can learn,” he says. “What you can’t learn is how to communicate on television—a skill Oprah had from day one. It was just so obvious. She was a genuine person, and it came across that way onscreen.” She invited him to her 50th-birthday party. As a gift, he framed two memos that he had written about her when she worked for him—one welcomed her to the station; the other marked her departure. “In that memo, I wrote, ‘Barbara Walters—watch out!’”
For nearly two hours, he sat with Kelley and recounted all of this. “[Kelley] puts you at ease immediately,” Clark recalls. “She makes you feel like a long-lost friend, someone you can really confide in.” And once an easy rapport has been established: “Then she asked about sex, drugs, and boyfriends. The interview ended shortly after I told her that I didn’t know anything about sex, drugs, and boyfriends when it came to Oprah.”
And so the clash of these two publishing colossi continues apace—its finish still many months in the future. But however the Mighty Oprah chooses to withstand the furtive mewing underfoot doesn’t much matter. Because there will be no stopping it. “I’ve interviewed hundreds of people across the country and am grateful to each for the time and consideration shown to me,” Kelley cheerfully wrote in an early e-mail to me. “Of course, I’m most grateful to Oprah Winfrey for giving me such a phenomenal life story to document. She’s a biographer’s dream.”
Photograph: Harry Borden/Corbis Outline