Oprah (18 page)

By 1983, Oprah had to decide whether to renew her contract with WJZ and stay a big star in a small sky, or try to find another job. She was torn, especially after Debra DiMaio, one of her favorite producers, left for Chicago. When Oprah was poised to sign a new contract, DiMaio called and begged her to hold off. She said a great job was opening up because Robb Weller was leaving
A.M. Chicago.
“For God’s sakes, don’t sign yet.” DiMaio urged her to send a tape and résumé to WLS, and on Labor Day, Oprah flew to Chicago for a formal interview.

Beforehand, she sat in her hotel room and watched the show. “I’d
never seen it before,” she said, adding that she was not impressed. “They baked cookies and gave you the latest in mascara techniques.” When she went for her interview, she told WLS management their show was no good. “Too frivolous! I’m best at combinations: A sexual surrogate one day, Donny and Marie Osmond the next day. Then the Klan.”

The general manager, Dennis Swanson, had already made up his mind about hiring Oprah, but just to make sure he auditioned her by setting up an interview with a group of sexually impotent men; then he told her to reminisce on camera about her deprived childhood and her time as a teenage runaway. “Her astute merger of prurience and uplift proved irresistible,” wrote Peter Conrad in
The Observer.
Offered the job on the spot, she jumped at it. “The country’s third market! My own show!”

Dennis Swanson was also dizzy with delight. “He was like a kid in a candy store,” recalled Wayne S. Kabak, then vice president of the talent agency ICM. “I had traveled to Chicago to visit a client I represented named Candace Hasey, who hosted WLS’s morning show. I stopped by to visit Swanson, her boss, who told me he had some bad news. He was going to fire Candy because he had found an extraordinarily talented replacement, who he thought would become a huge star. Notwithstanding that I was sitting in his office feeling rather downtrodden about Candy’s fate, Dennis was so excited about his discovery that he insisted on showing me the tape of the woman who was replacing my client. He put the tape in the machine showing Oprah in Baltimore and, in a flash, I knew he was right. If any executive should have reaped the huge rewards of Oprah when she finally hit syndication, it was Dennis, who sadly did not because the laws at the time prevented companies that owned networks from syndicating shows. Since ABC owned WLS, syndication rights were dealt to King World which made hundreds of millions, if not more, from Oprah.”

After her audition, she returned to Baltimore and called Ron Shapiro to negotiate her new contract. WJZ tried to keep her with inducements of a bigger salary (WLS was offering $200,000 a year), a company car, and a new apartment. “No one wanted her to go,” said Eileen Solomon, “and some tried to pressure her by saying she’d never make it on her own in Chicago.”

Bill Baker, then the chairman of Group W, called. “Oprah, you can’t leave WJZ,” he said. “Baltimore is your home. You’re the leading lady of the city. You must stay.” But Oprah had made her decision. Baker said he saw to it that Paul Yates, the general manager, was fired for letting her go.

Bill Carter felt that Oprah would succeed in Chicago, but he acknowledged that others did not. “There was an undercurrent of feeling here that this woman was not all that special,” he said. “I guess because people are used to turning on their television sets and seeing nothing but attractive women, sexy or whatever. They really didn’t see that substance in her. I think there’s an element of racism in that. Oprah is a very black-looking black woman….There were expectations that she would flop in Chicago.”

Seeing he was losing her, Paul Yates would not release her until her contract expired at the end of the year. Then he played rough. “There’s no way you can make it in Chicago up against Donahue,” he said. “It’s his home base. You’re walking into a land mine and you can’t even see it. You’re committing career suicide. You’re going to fail.” Yates, an African American, said Chicago was a racist city that had not been entirely welcoming to its first black mayor, Harold Washington, and certainly wouldn’t be welcoming to her. But Oprah had already factored race into her decision.

“I made a deliberate choice about where to go,” she said. “Los Angeles? I’m black and female and they don’t work in LA. Orientals and Hispanics are their minorities. New York? I don’t like New York, period. Washington? There are thirteen women to every man in D.C. Forget it. I have enough problems.” Chicago, the third largest television market in the country, seemed ideal. “It’s a big little town, sort of cosmopolitan country. The energy is different than Baltimore. It’s more like New York, but you’re not overwhelmed like in New York.”

Having decided to make the move, she now had to wait four months to finish her contract in Baltimore before starting her new job. “I thought the [Chicago] show might not survive without a host for that long. I started eating. First I ate to celebrate getting the job, then [I ate] out of insecurity. If I failed in Chicago, I could say it was because I was fat.” By the time she got to Chicago she had gained forty pounds.

“I was hired to take Oprah’s place as coanchor of
People Are Talking,
” said Beverly Burke, a television news reporter from North Carolina, “and it was a huge adjustment for me. But Oprah was great. She took me to lunch at the deli in Cross Keys and told me how the show worked. She talked candidly about Richard Sher, said he was Mr. Television—always on—and would totally dominate the show but that he was very good at what he does and quite professional….If it weren’t for Oprah, I wouldn’t have gotten that job. If not for her success, they would’ve been looking for a white coanchor….

“Still it was a huge adjustment for me. But I didn’t feel I had to be Oprah….She had never been an in-the-trenches reporter, which was more my style. Oprah was flash. She was criticized for showing up to do a news story wearing a fur coat.”

In the weeks before she left, Richard Sher teased Oprah on the air. “She’s leaving us behind and she’ll forget all about us in no time….Remember where you got your start.” Beverly Burke saw an edge to his teasing. “She was leaving him behind and everybody knew it.” But unlike others at the station, Sher encouraged Oprah. “I thought [the move] would be great for her,” he said years later. “I knew she would become as big a star as she has become.” As a going-away present, Oprah gave him a gold Rolex watch, on the back of which she had engraved, “Ope, 1978–1983.”

The decision to leave Baltimore was the most important of Oprah’s life, and she never forgot who encouraged her and who tried to hold her back. She remained close to Richard Sher, spoke at his synagogue, and even attended his sixtieth birthday party. Publicly, she said she would be forever grateful to Bill Baker for giving her the start, but inexplicably, she never spoke to him again, despite his illustrious rise in broadcasting to become president of WNET public television in New York. Upon his retirement in 2007 he was celebrated with a magazine of tributes from networks and esteemed television colleagues: Bill Moyers, Charlie Rose, Joan Ganz Cooney, Newton Minow, and Bob Wright. But there was no tribute from Oprah Winfrey. She never spoke to Paul Yates again, either, but when Skip Ball, an engineer at WJZ, was dying, she flew to Baltimore to spend time with him in the hospital.

In December 1983 the station threw her a farewell party at Café des Artistes in Baltimore, which her mother, Vernita Lee, attended with Oprah’s brother, Jeffrey. All of WJZ’s on-air stars showed up—Jerry Turner, Al Sanders, Bob Turk, Don Scott, Marty Bass, and Richard Sher. Paul Yates presented her with a Cuisinart, a photo album of her days at the station, a basketful of her favorite ballpoint pens, and a twenty-five-inch Sony Trinitron television, but the gift that brought her to tears was the life-size Oprah doll wearing a copy of her favorite dress, made by Jorge Gonzalez, the station’s makeup artist and graphic designer.

In her farewell speech, Oprah thanked everyone and praised Baltimore as the place where she grew up and became a woman. She then called Beverly Burke to the stage, gave her a warm introduction, and wagged her finger at the crowd, telling them to be nice to her.

Days later she packed up her five coats from Mano Swartz Furs and headed for Chicago, while Tim Watts quietly left town for Los Angeles to try to become a stand-up comic. For the next five months they planned to see each other on weekends, with Oprah flying back and forth to the West Coast. So leaving Baltimore was not as wrenching as she had anticipated. In fact, the future looked bright. Arleen Weiner drove her to the airport and kissed her goodbye, shouting down the terminal, “I hope you make it, hon….I hope you make it.”

U
NLEASHED AND
uninhibited, Oprah chewed up the talk show competition. Chicago television viewers had never seen an overweight black female host before, and they were knocked breathless by the tornado that whirled into their homes every morning, shaking the rafters and jostling the furniture. Accustomed as they were to the cerebral style of Phil Donahue, the raunchy antics of Oprah Winfrey were a jolt, especially when she charged into the no-go zone of tabloid sex. “She receives higher ratings with controversial shows on male impotence, women who mother their men, and guys who roll over after doing it,” observed the
Chicago Tribune
’s “INC.” column, “while Donahue tries to combat her with right-wing spokesmen and computer crimes.”

“I usually don’t do homework,” said Oprah. “I really have learned that for me and my style of interviewing, the less preparation I do, the better because what everybody is now calling Oprah’s success is me being spontaneous and that’s all it is.” The
Chicago Sun-Times
’s Richard Roeper disagreed. He said her success was due “largely to loud, self-centered and often cheesy programming.”

In your face and up your nose, Oprah left her audiences (and eventually Donahue’s) gasping and begging for more. “The difference between Donahue and me is
me,
” she said. “He’s more intellectual in
his approach. I appeal to the heart and relate personally to my audiences. I think it’s pretentious to think you can go into a lot of depth on a subject in only an hour.” Never plagued by self-inflicted doubts, Oprah appeared supremely confident, especially after Donahue moved from Chicago to New York City. The only signs of her internal combustion were nail-biting and nonstop eating. Otherwise, she seemed unintimidated by the talk show king. “We’re stomping him in the ratings, you know, and suddenly he’s gone [left town]. It was maaaahvelous.”

Publicly she flicked Donahue a modicum of respect (“He listens”), but privately she complained that for the six months they were both in Chicago he did not contact her. “He never called just to say ‘Hi Ope, welcome to town.’ ” She never forgot the slight.

Everyone else called, though, including Eppie Lederer, aka Ann Landers, the city’s most famous resident. Oprah sent her a $1,000 jeweled Judith Leiber bag to say thank you, and invited the advice columnist to be a frequent guest on her show. The welcome call that paid pure gold came from Dori Wilson, a former model who owned her own public relations firm. “As a black woman I wanted to reach out and help Oprah feel good about our city. So I invited her to lunch….She was the most driven person I ever met. Wanted to go straight to the top….I rifled my Rolodex for her and helped with publicity here and there, pitching stories to various publications….We became good friends for several years. Then, well, I guess you could say she dropped me.”

During their first lunch, in 1984, Oprah asked Dori to recommend a lawyer/agent, and Dori called her friend Jeffrey D. Jacobs. (“The
D
is for
dependable,
” Jacobs told clients.) “Jeff was then with Foos, Meyers and Jacobs and represented a lot of talent in Chicago, including Harry Caray [broadcaster for the Chicago Cubs] and the boxer James ‘Quick’ Tillis.”

In Jacobs, Oprah found a Moses to lead her to the Promised Land. It was like Sears meeting Roebuck. Over the next eighteen years Winfrey and Jacobs built the House of Oprah, but then, just as Sears dropped Roebuck, Winfrey jettisoned Jacobs. Their friendship fractured over professional jealousies, and Oprah decided to reign over her own kingdom—one monarch, not two. She no longer wanted a partner, especially a hard-charger like Jacobs, whom she once described as
“a piranha, which is what I need.” By 2002 she was ready to be her own piranha. Following their acrimonious split, the lawyer was able to walk away from Harpo having earned approximately $100 million, with Oprah worth $988 million. “One of the reasons she is so financially successful,” said Jacobs before their split, “is that we understand it’s not just how much you make, but how much you keep.”

Fortune
magazine described Jeff Jacobs as “the little known power behind the media queen’s throne”; others called him “Oprah’s brain.” As her consigliere for almost two decades, he handled every aspect of her business, becoming her lawyer, agent, manager, financial advisor, promoter, protector, and confidant. Keeping it further in the family, Jacobs’s wife, Jennifer Aubrey, became Oprah’s dresser, until
TV Guide
gave her its “Worst Dressed” award. Then Aubrey was jettisoned.

Within months of their meeting in 1984, Oprah became a full-time job for Jeff Jacobs, and by 1986 he had left his law firm to become her in-house counsel. He negotiated her contracts, supervised her staff, and oversaw production of her show. He also managed her endorsement opportunities, her speaking engagements, and her charitable contributions. He foresaw the future market for branding and pushed her to establish Harpo, Inc. (
Oprah
spelled backward); she was so grateful that she gave him 10 percent of the company and made him president. Having refused to hire an agent, a manager, or an attorney—“I don’t get why anyone would want to pay 40 percent of their earnings in commissions and retainers”—she felt she got full value from Jeff Jacobs. “If something were to happen to him, I don’t know what I would do,” she said. “I don’t know.”

Oprah became an immediate sensation in Chicago, leaving in her wake nothing but breathless admirers. Cabbies honked, bus drivers waved, and pedestrians hugged her. People on the street ran into restaurants just to watch her eat. “These are the glory days, I’ll tell you,” she told the writer Lyn Tornabene. “I walk down the street and everyone is saying, ‘Opry, how ya doin’?’ ‘Hey, Okra, how ya doin’?’ ” She even surprised herself with her success. “I’ve always done well,” she said, “but I didn’t expect it to happen this fast. I even did well in Nashville. People would call and say, ‘You’re all right for a black girl.’ The callers meant well.”