Oprah

by Kitty Kelley

  Even in retirement, Sher was unapologetic about the tabloid-like shows that he and Oprah did on People Are Talking. “When sex got big, we did shows on the man with the micro-penis. We did the thirty-minute orgasm. We did a lot of the tough topics—the transsexual mother with brittle bone disease.”

  One of their most exploitive shows became meaningful to Oprah and altered her way of thinking. The guest was a transsexual quadriplegic whose boyfriend’s sperm was inserted into her sister. The quadriplegic became the biological aunt/uncle and also adopted the child. The show was criticized when it aired, but afterward Oprah happened to see the child with the transsexual quadriplegic.

  “It was just a moving thing,” she said. “I thought, ‘This child will grow up with more love than most children.’ Before, I was one of those people who thought all homosexuals or anything like that were going to burn in hell because the Scriptures said it.”

  At the time, Oprah’s strong Baptist beliefs were being tested because of her intimate involvement with Tim Watts, a married man with a young son and no intention of leaving his wife, Donna.

  “He was her first real love,” said Oprah’s sister, Patricia Lee Lloyd.

  “Oh, God,” said Barbara Hamm, remembering when Oprah was so depressed over Tim Watts’s breaking up with her that she could not get out of bed for three days.

  Arleen Weiner, the producer of People Are Talking, recalled “the many, many tearful phone calls at one, two, three, four in the morning.”

  The women on the production staff were sympathetic and did all they could to help Oprah, who was so obsessed with the six-foot-six disc jockey that she once ran after him in her nightgown and threw herself on the hood of his car to try to make him stay with her. Another time she blocked the front door of her apartment, screaming, “Don’t go, don’t leave,” and then threw his keys down the toilet. This was the story she later told Mike Wallace on 60 Minutes, attributing it to her more benign relationship with Bubba Taylor.

  After Watts walked out on her at 3:00 A.M., she called her best friend, Gayle King, who she knew had been in a similar situation. “For her it wasn’t throwing keys, it was checking the odometer,” Oprah said of King. “We both have done equally crazy things. I was on the hood, but Gayle was on the bumper. So because she has been there and lived in that place, she never judged me. But she was always there to listen and support me.”

  The men on staff were not so tolerant of Oprah’s hysterics. More than two decades after working with her, Dave Gosey, the director of People Are Talking, could not say one kind word about her. “My mother told me if you can’t say something nice about someone, say nothing at all. So I have nothing at all to say about Oprah Winfrey.”

  Her volcanic affair with Tim Watts started in 1979 and crested and cratered for five years, even after she left Baltimore and moved to Chicago. “Those years were the worst of my life,” she said. “I had bad man troubles.” Being in love with a married man meant snatched hours, empty weekends, and lonely holidays that left her feeling desperate and forlorn.

  “Poor thing. She had to spend Thanksgiving with us one year [1980] because she had no place else to go,” said Michael Fox, whose parents, Jim and Roberta Fox, were close to Richard and Annabelle Sher. “We didn’t know her until the Shers brought her to our house….I sat next to her at dinner. She ate so much food that night I couldn’t believe it. I’ve never seen a human being eat as much as Oprah did….Paul Yates [WJZ’s general manager] told me about her affair with Tim Watts and how miserable she was.”

  Oprah did not mind being seen in public with a married man, but when she found out that he was also having an affair with a pretty young blonde, she said she felt “devastated” about being “two-timed.”

  “My affair with Tim started in 1980 [in the midst of his with Oprah],” said Judy Lee Colteryahn, the daughter of Lloyd Colteryahn, a former football star from the University of Maryland who played for the Baltimore Colts. “Tim always said that Oprah couldn’t know about us because it would ruin his business opportunities [with her]….He led me to believe that he was only seeing her to get a job at Channel 13….He did get a weekly Sunday show there for a while….So I didn’t pay much attention at first, but then my friends started seeing Tim and Oprah having dinner at The Rusty Scupper when he was supposed to be with me….He played basketball for the station on Friday nights, so one night I walked into the gym [unexpectedly] just as they were finishing up a game. I saw Tim walk over to the bleachers with his cowboy boots and hand them to Oprah. He leaned over, whispered in her ear, and she started walking out with his boots. Then he saw me. ‘What are you doing here? You need to go home right now. Right now. I’ll be over later.’ That’s when my jealousy of Oprah started….Then I found her credit cards in his pockets….She really took good care of him….He was always broke….But he returned the favor later by keeping his mouth shut.”

  When Oprah became famous the tabloids pursued Watts and offered to pay him for the story of their love affair, including details of their drug use. “He called Oprah, said he didn’t want to talk but he was strapped for cash,” said Judy Colteryahn. “He said, ‘Look at it from my point of view. I don’t want to talk to these people, but I sure could use some money. I’ve got kids, I’ve got bills, but I am a friend to you….What can we work out?’ That’s what he told me.

  “That Christmas [1989] Gayle King delivered a gift-wrapped box to Tim in Baltimore, and Tim called me down on the Eastern Shore, where I was staying with my parents. He said, ‘Oprah came through. Big-time. She really came through. Fifty thousand dollars, cash. Get your butt back here. We’re going out for New Year’s Eve.’

  “Naturally I drove right back to Baltimore. Like Oprah, I was always available for Tim. Like her, I was always hanging out the window waiting for him to drive up in his blue Datsun. But…she was smarter than me. She only wasted five years of her life on him. I wasted more….I did not intend to fall in love with a black man….Tim is very light-skinned, so I told my friends that he was mulatto….I nearly fainted the first time I saw a picture of Stedman Graham, because he looked exactly like Tim: tall—six-foot-five or six-foot-six—handsome, with a mustache, and very light-skinned. I thought, ‘Wow. Oprah has found a replica for Tim in Stedman.’ ”

  That New Year’s Eve, Oprah’s gift of $50,000 in cash financed her former lover’s trip to Atlantic City with Judy Colteryahn. “Tim got a limousine and we had a big fancy hotel and front-row seats in Remo, a black jazz club….At the time I thought he was a great guy for not selling Oprah out, especially on drugs, which we did all the time in those days….Now that I’m older I realize how much power Oprah had and what she could have done [to him]. So they probably both had nooses around each other’s necks.

  “I asked [him] what he could say [to the tabloids] that would make Oprah pay him fifty thousand dollars in hush money not to talk….That was big money then [$50,000 in 1989 equals $86,506.85 in 2009]….I was wondering what he knew about her….He said she did not want him to talk about her brother being gay [Jeffrey Lee died of AIDS December 22, 1989]. It’s no big deal to have a brother who is homosexual, but apparently it was to Oprah….Tim also said he knew about some lesbian affairs or whatever….But that’s all he said, and we never went into it.”

  Oprah never revealed Tim Watts by name as the man who had brought her so low in those years. Over the next two decades she referred to him on television as a “jerk,” frequently telling her audience of the debasements she had endured because of him. “I was in love; it was an obsession,” she said. “I was one of those sick women who believed that life was nothing without a man….The more he rejected me, the more I wanted him. I felt depleted, powerless….There’s nothing worse than rejection. It’s worse than death. I would wish sometimes for the guy to die because at least I could go to the grave and visit….I have been down on the floor on my knees crying so hard, my eyes were swollen…then it came to me. I realized there was no difference between me and an abused woman, who has
to go to a shelter—except that I could stay home.”

  African American women understand in their bones the slave mentality that leads sisters like Oprah to give their all to a man in complete subordination. One friend explained Oprah’s obsession with Tim Watts and his rejection of her by citing Toni Morrison’s novel A Mercy, in which a freed black man rejects a slave woman for not owning herself and for being a slave to her desire for him. Oprah tried to fight her own slave mentality but acknowledged through the years that she struggled not to surrender. “There’s always a teeny, tiny little conflict that says, ‘Maybe you already have enough. Why do you keep pushing?’ That comes from lack of self-esteem, from what I consider to be a slavery mentality.” Three years later she was still fighting it. “Every year I ask God for something. Last year it was love. This year it’s going to be freedom…from everything that’s kept me in bondage.”

  Oprah was still raw from being rejected by Watts when she told Cosmopolitan magazine in 1986, “If I start to talk about it, I’ll weep on the floor. But I tell you, I will never travel that road again. The next time somebody tells me he’s no good for me, I’m gonna believe him. I’m not going to say to myself, ‘Well, maybe I’m too pushy, or maybe I don’t talk enough about him, or maybe, maybe, maybe. I’m not racing home to meet him there and then not hear from him until midnight. Uh, uh. Too painful.”

  Even when she was supposedly happy in a committed relationship with Stedman Graham, she continued to refer to her doormat days with Tim Watts. In 1994 she told Entertainment Weekly that she was reading her journal from that time and was chagrined by her pathetic musings: “ ‘Maybe if I was rich enough or famous enough or was witty, clever, wise enough, I could be enough for you….’ This is a guy I used to take the seeds out of the watermelon for so he wouldn’t have to spit!”

  Twenty years after the affair she was still talking about him, unable to put the past to rest. In 2005 she told Tina Turner, “I just ran across a letter I wrote in my 20s, when I was in an emotionally abusive relationship. I’d written 12 pages to one of the great jerks of all time. I wanted to burn the letter. I want no record of the fact that I was ever so pitiful.” In 2006 she told London’s Daily Mail, “I will never be in a position where I love someone else more than myself, where I give over my power to someone else. I will never be in a position where I get in my car and follow them to see if they are going where they said they were going. And I’ll never be in a position where I’m looking in someone’s pocket or their wallet, or checking who they are on the phone with. And I will never be in the position where, if they lie to me more than once, I don’t end that relationship.”

  During her affair with Watts, Oprah was living well in Baltimore, making $100,000 a year. She described herself then as young, attractive, and still slim. “I had so much going for me, but I still thought I was nothing without a man.” She had moved into a pretty two-bedroom apartment in Cross Keys and bought a BMW. “I still remember one day we were hanging out and she transferred five thousand dollars from her savings account to her checking account just for the thrill of being able to do it,” said Barbara Hamm.

  Professionally, Oprah’s star was shining. She and Richard Sher had become the toast of Baltimore as their show began outdrawing Phil Donahue’s in the local ratings. They were so successful that their producers decided to go for syndication, which for Oprah rang the bells of big money and national recognition. It was the main reason she stayed at WJZ after her close friends Maria Shriver and Gayle King moved on to bigger markets.

  Oprah and Richard shared the same agent, Ron Shapiro (“That’s Sha-pie-row,” the lawyer instructed), and she insisted he write into her new contract that if she wasn’t working on a syndicated show, she could leave the station at the end of two years (1983) instead of three. So confident was everyone of syndication success that they signed off on the clause without objection.

  In March 1981, the staff of People Are Talking went to New York City for the annual NATPE (National Association of Television Program Executives) convention, where syndication deals are made. They rented a suite in the New York Hilton decked out with signs that read: “The Show That Beats Donahue.” Richard and Oprah held court with programming executives from around the country and sold the show in Rockford, Illinois; Minneapolis, Minnesota; and Sacramento, California, with potential deals in Milwaukee, Wisconsin; Bangor, Maine; Santa Rosa, California; and Casper, Wyoming. Unfortunately, none of the prospective buyers was a number one station offering a good time slot, but the producers still remained encouraged.

  In anticipation of national exposure, Arleen Weiner hired an image consultant to help Oprah achieve a more sophisticated look. Up to that point she had been shopping at funky little stores such as The Bead Experience. “We were close to WJZ, a one-size-fits-all kind of store with gauzy, flowy tunics and caftans and palazzo pants,” said Susan Rome, who was sixteen years old when she helped Oprah. “I tried to get her away from always buying fat-lady clothes in dark colors because she really wasn’t fat—just a bit chunky and thick—but she was very uncomfortable with her size.”

  When the paid image consultant arrived, she met Oprah at her apartment and tore through her closet. “I was hired to give her an easier, more comfortable fit, and a look that was more stylish but would still play in Peoria,” said Ellen Lightman. “There was a little trepidation on her part in the beginning, which is only natural for someone who has been directed to update her style and improve her image….We retired all her beiges and camels, got her into jewel tones and clothes that fit better and were more flattering to her full figure.”

  The show also began booking more celebrities, for a broader appeal, which gave Oprah the chance to meet and interview Muhammad Ali, Maya Angelou, Pearl Bailey, Dick Cavett, Uri Geller, Jesse Jackson, Erica Jong, Ted Koppel, Barry Levinson, and Arnold Schwarzenegger. People Are Talking also became a major stop for authors on book promotion tours. “I remember being interviewed by Oprah the day after Ronald Reagan was elected president,” said the writer Paul Dickson. “During a commercial break she talked about how awful Reagan was going to be for the country. She was very upset. ‘This man will not be good for my people,’ she said.” But she said nothing on air because she was prohibited by contract from publicly expressing any political opinions.

  Within six months it became clear to the producers that syndication was not going to happen. At its peak, the show was aired by only seventeen stations. Despite Oprah’s great warmth on air, People Are Talking was simply too parochial to go national.

  “The general manager after me was Art Kern, and he sold the show to half a dozen stations, but there was resistance within Westinghouse,” said William F. Baker, by then chairman of Group W. “The guy in Hollywood below me did not think Oprah would make it as a talk show host….I told Baltimore we were not to lose Oprah because she was a massive asset, but Baltimore was our smallest station and so the one I paid least attention to.”

  On Monday, September 7, 1981, the dreaded headline appeared in the TV and Radio section of The Baltimore Sun: “ ‘People Are Talking’ Flops as Syndicated Show.” Richard Sher was disappointed, but Oprah was devastated. This was her second big public failure in Baltimore. That evening she had another row with Tim Watts and he walked out on her, slamming the door on her hand.

  “The problem with you, baby doll, is you think you’re special,” he said. As Oprah recalled, she was on the floor crying: “ ‘I’m not, please. I don’t think I’m special. I don’t, please come back.’ Then, as I went to pick myself up, I caught a glimpse of myself in the mirror and I saw an image of my mother and I remembered her screaming one night when her boyfriend had left her. And I remembered my cousin, Alice, saying, ‘It’s all right. He’s coming back.’ That same cousin was in an abusive relationship. Her boyfriend had knocked her down the stairs and broken her leg and arms, and she still took him back. I saw myself through their eyes in that mirror. I always said I would not be a battered woman. I would not b
e screaming for some man. And when I heard myself saying, ‘Come back. I don’t think I’m special,’ I’d become that. I got myself up, washed my face and said, ‘That is it.’ ”

  At 8:30 P.M. on September 8, 1981, she wrote a note to Gayle King, saying that personally and professionally her life did not seem worth living. “I’m so depressed, I want to die,” she wrote. She told Gayle where to find her will and her insurance policies. “I even told her to water my plants,” Oprah said later. She told the writer Barbara Grizzuti Harrison that she had not considered the ways and means to accomplish her death. “I didn’t even have the courage to end the relationship,” she said. Years later Gayle returned the note to Oprah, who said, “I see it now as a cry of self-pity. I never would have had the courage to do it.” She told her audience: “The whole idea that you’re going to kill yourself and they’re all going to be mourning—that’s not really the reality. I realized that if he even came to my funeral he would go on with the other girl and on with his life and still be happy.”

  The one-two punch of losing syndication, plus the love of her life, seemed unbearable at the time. Her friends were concerned enough to keep a quiet suicide watch, and one gently suggested that she seek psychotherapy, but Oprah refused. “I was so adamant about being my own person that I wouldn’t go for counseling,” she said. Her only solace was her star status in Baltimore. “She was known and loved throughout the city,” said WJZ’s former executive producer Eileen Solomon. “In that era Baltimore was still pretty much a town that saw itself in the shadow of Washington, D.C., with more of a blue-collar sensibility.” And Oprah was its queen.

  “She was a very big deal here,” said Bob Leffler, “and we’re a sports town, where the biggest celebrities are baseball and football stars….I remember seeing Oprah at Ron Shapiro’s spring party, where everyone ignored legendary Orioles like Eddie Murray and Jim Palmer and flocked to her….Now that’s saying something for Baltimore.”