Maclean's Interview: Biographer Kitty Kelley

On Oprah Winfrey’s grudges, her sexuality, her long-time fiancé, and her father’s talk of ‘dark secrets’

Oprah Winfry, Secrets

Photograph by Steve Simon

Kitty Kelley, queen of the unauthorized biography, has written bestselling tell-alls about the royal family and Frank Sinatra, among others. Oprah Winfrey, queen of daytime confessions, denied Kelley’s repeated requests for an interview for her new biography, Oprah.

Q Was it harder to get people to talk about Oprah than about your previous, famously private subjects Jackie Onassis or Nancy Reagan?
A: They’ve all been very hard, but in this case, it was extraordinarily difficult because present and former employees are terrified to speak. They signed confidentiality agreements, so they’re afraid they will be sued.

Q: And Oprah bears a grudge, doesn’t she?
A: She’s not a screamer. She says she has “a disease to please,” so she wouldn’t confront you directly. But if you displease her, a curtain falls, and it is never, ever lifted. The displeasure can come from anything: asking her for a quote for a book or, in the case of one Chicago photographer who took quite glamorous pictures of her, recommending that she wear black lipstick—she never spoke to him again. [MetaFitness author] Suzy Prudden had done Oprah’s show many, many times, but then in promoting Suzy’s column the tabloids called her “Oprah’s exercise instructor,” and that was enough.

Q: What are the differences between Oprah and her TV persona?
A: There are two Oprahs. What you see on television is a woman who is just wonderfully warm, embracing, humorous. At other times you get an idea of a very cold and aloof woman. On camera, she can be totally charming. Off camera, she’s very removed, almost anti-social, which is hard to believe.

Q: Is she like that with celebrities, too?
A: No, she loves celebrities. They get the on-camera version.

Q: What surprised you most about her?
A: That this is a woman who appears to be so open and uninhibited, but she is absolutely choked by secrets. Some of the secrets she’s revealed, mainly because she’s been forced to. For instance, when one of her former lovers claimed they’d done drugs together, crack, she denied it, denied it, denied it. She only admitted it when he sued her, and under oath, she had to. The same thing with having a baby [when she was 15]. Her sister sold the story to the tabloids, and then Oprah had to admit it. [Talking about her secrets has sometimes] been so helpful and beneficial to others. For instance, revealing that she was sexually molested from the age of nine to 14 helped a lot of people, by bringing that taboo into the public arena.

Q: Does she have any secrets left?
A: Other secrets have shackled her. As she herself said in her autobiography [which Oprah withdrew pre-publication in 1993], during her teenage years she was a prostitute. And I got hauled into the secrets. Her Aunt Katharine told me who Oprah’s [biological] father is, and then told me I couldn’t tell because Oprah doesn’t know. Aunt Katharine feels it’s Oprah’s mother’s place to tell her. I wondered why her mother hasn’t, and Aunt Katharine said, “Because I don’t think she wants to revisit it at this stage of the game.”

Q: She isn’t close to her mother. Why not?
A: I think she blames her mother for putting her in a situation where the sexual abuse could happen. Also, she really dislikes her mother for being greedy. Oprah’s been very good to her financially, but she will not give her mother her phone number.

Q: Oprah’s father really turned her life around when she was out of control as a teenager, and she’s acknowledged his influence. Are they close?
A: No. When I interviewed Mr. Winfrey in Nashville, he was very angry and upset because Oprah had called and asked why he was writing a book about her. He said, “It’s not about you, it’s about my life,” and she said, “Well, the only reason anyone would be interested is because of me.” He loves Oprah, but it’s a complicated relationship because he knows he doesn’t get that love in return. Yet she is very good to him financially.

Q: He told you that he’s disappointed in the ways she’s changed and, alluding to “dark secrets,” said, “I know the truth. So does God and so does Oprah. Two of us remain ashamed.” What was he talking about, exactly?
A: I think he was talking about the sexual promiscuity and the prostitution. He didn’t go into great detail about speculation around Oprah’s friendship with Gayle King, but he was so indignant about Gayle King. He called her “that girlfriend of Oprah’s.”

Q: And also a “dirt hog” and “street heifer.” Why?
A: He dislikes Gayle because she told him not to write his book. And it seems like there’s more than that, but he didn’t say. I said, “You sound so disappointed in your daughter, she’s the most admired woman in the world.” But he doesn’t admire her New Age guru beliefs, the fact that she no longer believes Jesus is her saviour. He said, “She was raised in the church, and she’s left the church.”

Q: A number of family members talked to you about what they call “Oprah’s lies.” Which lies most upset them?
AHer Aunt Katharine and her sister felt that Oprah exaggerated the conditions in which she was raised, by saying she never had dresses and spent the first six years of her life barefoot, that her only playmates growing up were the pigs that ran around her grandmother’s farm—those are the kinds of things the family objects to. Oprah says, “People don’t want to hear the truth, they want drama.”

Q: Do you think, given the thousands of interviews with Oprah that you’ve reviewed and the hundreds you’ve conducted with people who know her, that she is generally truthful?
A: It depends how you look at exaggeration. For instance, Oprah tells a very funny story about working at a Baltimore TV station. She claims that the dunderheaded male management wanted to remake her, wanted her to have plastic surgery on her nose, change her look, and so they sent her off to a hair salon where they did a permanent that caused her to lose some of her hair. But her co-workers at that time say that because she had done so poorly at the station in the beginning, and because she was under a great deal of stress, she started losing her hair. Oprah is quite right that people do love drama, so she gives them a very dramatic story.

Q: You reveal that she dumped her long-time friend Eppie Lederer, a.k.a. Ann Landers, after she told Oprah she’d heard “distressing stories about Stedman Graham’s sexual preferences.” Is Oprah in denial about her long-time fiancé?
A: She used to talk about all the wonderful sex they had when she got thin. But I think they share something beyond that. They know each other very, very well. He looks upon her as someone very special. He’s very spiritual. And he likes Gayle—that’s a good thing, I guess, because Oprah is with her all the time. Oprah says that they could never have been married because both of them are wedded to their careers. That tells you something about their priorities: work comes first, not each other.

Q: You strongly imply their relationship isn’t romantic.
A: There’s been a great deal of speculation about Oprah’s sexuality, and she’s put it into the public domain by continually denying that she’s gay. Maybe five years ago, based on everything I know, I might’ve suggested “bisexual.” But now that Oprah is 56, I would really say that she is asexual. I think she has poured all of her sexual energies into her career. In an interview [years ago] with a black entertainment magazine, she said, “I don’t really consider myself a sexual being.” I’m taking her at her word for two reasons. I think sexual molestation leaves scars that are rarely healed, and healing has to be done with therapy, none of which she’s had. The other thing is that she had a tumultuous four-year affair with a married man in Baltimore that truly brought her to her knees, and I don’t think she’s ever been able to fully trust a man since then.

Q: Oprah was very confident even as a teenager, predicting she’d be rich and famous. But as she became successful, she started saying things like, “I know people really, really love me, love me, love me?.?.?.?Being able to lift a whole consciousness—that’s what I do.” Why?
A: She has got an entire corporation, about 500 employees just within Harpo, and as one of them described it to me, it’s a cult. She’s got more than yes-people around. She has adorers. It’s like a church.

Q: What matters most to her?
A: In the beginning it was money, she was determined to be the richest black woman in America, and she was very smart to camouflage that. Now, I think what makes her happiest is probably what makes all of us happiest: being with family, but in her case she views her friends as her family. The thing I think that makes her unhappiest goes back to the secrets again: the secret eating—it’s just trying to fill some mammoth hole inside her that she cannot fill. I think it creates a lot of anxiety that she doesn’t look the way she’d like to look.

Q: There’s a memorable incident in the book when she orders two pecan pies from room service and gobbles them both in an hour.
A: It’s the total excess. And pecan pies! They’re so sweet and rich.

Q: She has a reputation as an über-philanthropist, but looking at your research, her donations are relatively small given her income—yes, she gives millions, but she makes hundreds of millions a year. Is she generous?
A: The only way to ever say with any kind of accuracy or fairness is to do what I did: pull all the tax returns, and list the information so readers can see it. It’s interesting, too, that she’s like Donald Trump, everything has to be named after her—she does make sure that you know about her giving. Now, maybe she’s doing this to stimulate giving from others. But [her philanthropy] is not commensurate with the amount of money she makes, no. That’s part of the difference between the public image and the private reality.

Q: She’s a very contradictory person. On one hand, clearly a brilliant businesswoman with sharp elbows. On the other hand, susceptible to flaky ideas like those in The Secret, namely that you get what you wish for.
A: She does not see that timing or luck has had anything to do with her success. She feels that she wished for it and wanted it, and that’s why she got it, and you can do the same.

Q: Maybe the weirdest thing about her is her penchant for bathroom humour.
A: The occasion that threw me the most was when she was giving a speech at the Holocaust Museum and started talking about how hard it is to be famous, that she’d used the restroom and the woman in the next stall told her, “You pee like a horse.” It was such a bizarre statement to make in a situation where you’re remembering the devastation of concentration camps. She also talked about peeing when she went back to her hometown for Oprah Winfrey Day and at a graduation ceremony at Wesleyan College. I was there for that one, and people were stunned. But you know, that potty humour makes Oprah seem as country as cornbread, and maybe that’s why she does it.

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