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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