Oprah (41 page)

She admitted years later that she was sad at her best friend’s wedding. “I just didn’t think it was going to work out,” she told Gayle in a joint interview in 2006. “You know how you go to weddings and they’re full of joy….I didn’t feel that at yours….It just felt it was kind of pitiful. I never told you because it wasn’t my place to say that….Maybe I couldn’t feel the joy because I was feeling like our friendship was going to change. But it didn’t.”

That was unfortunate for Gayle’s husband. “I knew them well in the early days [1985–1990],” said Oprah’s good friend Nancy Stoddart. “Nile and I took ski weekends with Oprah and Stedman, and spent country weekends with Gayle and Billy. He was a cop then…and there was no way he could [provide for Gayle the way Oprah could]. He was pretty resentful of the effect that Oprah’s fame was having on their relationship….Billy later went to Yale Law School, became a lawyer, and is now assistant attorney general for the state of Connecticut….He’s done great stuff for himself….At the time, he wanted to provide
his family with a new house, but Oprah came in and bought Gayle a one-million-dollar home, which in those days was huge—just huge.”

Gayle divorced Bumpus in 1992 because, as she said, “he cheated,” and Oprah encouraged her to leave him rather than forgive his extramarital affair. “I’ve been to five therapists,” Gayle said, “and nobody’s been better than Oprah in terms of [my] marriage/life counseling.” Bill Bumpus told a reporter in 1992 that he blamed Oprah for the breakup. “She didn’t mean to hurt us, it wasn’t malicious, but she ruined our marriage with her generosity and her insistence on taking up so much of Gayle’s time. There probably are lots of husbands who complain about their wives watching
Oprah,
but at least they can turn off the television set. They don’t have Oprah calling at all hours of the day and night. They don’t have her buying their wives expensive presents. They don’t have her giving their families things they can’t afford….” In the divorce, Bumpus paid one dollar and signed over to Gayle ownership of the million-dollar house Oprah had purchased.

By the time of Oprah’s fortieth birthday, Gayle had been divorced two years. She continued to live and work as an anchorwoman in Connecticut, in order to share with her ex-husband custody of their two children. Oprah flew her back and forth to Chicago so they could spend more time together. Gayle described those trips as episodes from
Lifestyles of the Rich and Famous.
“The limo picks you up and everything is taken care of. You can literally go [to see Oprah] with five dollars in your pockets and return with $4.99—because you spent a penny for some gum.”

For the celebration of her fortieth, Oprah had emailed her staff, which always fêted her birthdays, that no gifts were expected and none would be accepted. But for the special party in California, “40 for Oprah’s 40th,” as the engraved invitations read, she relented and said guests could bring a copy of their favorite book for her library.

“All year Oprah’s been looking forward to turning forty,” said Debra DiMaio. “For her it is part of a very positive milestone.”

At a cost of $130,000, she flew everyone, including Stedman, Gayle, Maya Angelou, select members of her staff, her private photographer, and her five bodyguards, to Los Angeles on a private jet and gave them all $1,000-a-night suites at the Hotel Bel-Air. The
celebration began with a dinner Friday evening at L’Orangerie that, according to press reports, cost more than $15,000. In a long white gown, Oprah, escorted by Stedman, greeted guests, including Steven Spielberg, Tina Turner, Julius “Dr. J” Irving, Quincy Jones and Nastassja Kinski, Maria Shriver and Arnold Schwarzenegger, and Sidney Poitier and his wife, Joanna. Oprah’s photographer took pictures of everyone with Oprah, got them developed, placed them in sterling-silver frames, and gift-wrapped them by the end of the evening so that she could give each guest a memento of the dinner, just like Queen Elizabeth II does for guests at state dinners.

The next day, Debra arranged for a fleet of black stretch limousines to chauffeur everyone to lunch at The Ivy, to Montana Avenue in Santa Monica for a shopping spree, and then to the home of Maria Shriver and Arnold Schwarzenegger for a tea party. That night, leaving spouses and partners behind, the women headed for Oprah’s bungalow for a slumber party.

During that evening they brainstormed about what they could do to extend Oprah’s spiritual reach. Each believed that Oprah was a blessed disciple, a special messenger sent from God to do good. Maya Angelou later put the feeling into words: “In a queer way…she holds a spiritual position not unlike Norman Vincent Peale once did. Each culture and each time has its…moral mountains that we looked up to….These are people, who, to lesser or greater degrees, are really the lights, the pinnacles of what is right and kind and true and good and moral. Well…she’s sort of that.”

Sipping Cristal champagne (Oprah’s favorite), and led by her spiritual guru Marianne Williamson, self-described as “the bitch for God,” the women decided that Oprah should contact the Pope, and together the two of them could lead the world in a weekend of prayer. No one voiced the slightest concern that an American talk show host might appear slightly brazen to be calling the Vatican to arrange a global pray-in with His Holiness. The papal weekend never took place, but such was Oprah’s power at the time that national leaders—U.S. senators, presidential candidates, First Ladies—clamored to be on her show. Being in a position to pick and choose her guests, she no longer granted access to just any important personage. When it was suggested that she
should interview Mother Teresa, the nun who ministered to the poor of Calcutta, Oprah vetoed the idea. “I don’t think she’s much of a talker,” she said. “That would be a long hour on television.”

The all-female slumber party ended with a group prayer led by Marianne Williamson, and Oprah left determined to present more spiritual and less sensational shows in the future. “I’ve been guilty of doing trash TV and not even thinking it was trash,” she told
Entertainment Weekly.
She later made a mea culpa to
TV Guide
and resolved to elevate her shows. Her timing was perfect. Within a year, William Bennett, who wrote the bestselling
The Book of Virtues,
joined forces with Senator Joseph Lieberman (D-Conn.) to denounce daytime television talk shows and the companies that produced them. Bennett, who was contemplating a presidential run in 1996, exempted Oprah and Phil Donahue because he had been on their shows to promote his books, but he castigated the hosts, owners, guests, advertisers, and viewers of Jerry Springer, Sally Jessy Raphael, Ricki Lake, Jenny Jones, Montel Williams, and Geraldo Rivera, saying they all must share the blame for the televised “rot” that “degrades human personality.” A few years later Bennett, satirized as “The Virtues Czar,” was publicly exposed as a compulsive gambler, and he apologized for blowing $8 million in Las Vegas, but his rant on rot had been effective. Procter & Gamble, the nation’s biggest daytime television advertiser, announced its decision to pull $15 million to $20 million in advertising from four daytime talk shows, and Sears, Roebuck and Co. did the same, citing “offensive content” as the reason.

Flying back to Chicago after her birthday celebration, Oprah felt she had launched her forty-first year in great style. Finally in shape thanks to Bob Greene and his twice-daily workouts, she announced she was starting to train for the Marine Corps Marathon in October. Having pared herself down to a trim size eight, she again decided she would never need her “fat” wardrobe, so she staged a benefit sale of nine hundred dresses, plus hundreds of pants, blouses, and jackets, at the Hyatt Regency in Chicago for two thousand of the fifty thousand viewers who sent in postcards for tickets. She reserved fifteen special outfits to sell at a silent auction, including the purple sequined dress she had worn to the premiere of
The Color Purple
in 1985. She raised
$150,000, which she donated to Chicago’s Hull House and to FamiliesFirst in Sacramento, California.

The day before the
The Oprah Winfrey Show
was to go on summer hiatus in 1994, her senior producers presented her with their ultimatum: Either the “dictatorial” Debra DiMaio goes or we go. Having lost a dozen producers and associate producers over the last two years, Oprah could not afford any more staff upheaval. So she called in her executive producer, who was also vice president of Harpo, one of her oldest friends, and her closest professional colleague, and allowed her to resign. DiMaio signed a lifetime confidentiality agreement that she would never speak or write about her association with Oprah, and she walked out of Harpo with a check for $3.8 million. Oprah was now without the hard nose and soft shoulder of the woman who had functioned as her alter ego for the past ten years. Within the industry the unexplained departure of DiMaio, who had launched Oprah into national syndication and kept her at number one, resounded like thunder. Her successor, Dianne Hudson, pledged to keep the show “out of the talk-show gutter.” Oprah immediately closed the studio, dispatched her staff, and disappeared on vacation, where she was “not available” for media calls, all of which fell again to Colleen Raleigh, her publicist.

In losing DiMaio, Oprah had lost her executive producer, chief of staff, party planner, confidante, nanny, and buffer against Jeff Jacobs. As a consequence, she became even more dependent on her personal assistant, Beverly Coleman, who soon caved under the strain and resigned two months later, saying she was “totally burned out.” Oprah offered her $1 million to stay, but Beverly said she could no longer take the twenty-four-hour workdays.

Then, in September, Colleen Raleigh gave notice, and a few weeks later she sued Oprah for breach of contract, claiming she had been promised $200,000 in severance pay, $17,500 in back pay, and $6,000 in vacation pay. “As a public relations professional with a reputation as a reliable and honest source, she was no longer able, in good conscience, to foster the image of Oprah Winfrey,
The Oprah Winfrey Show,
and Harpo as happy and harmonious and humane,” said Raleigh’s lawyer. “She was continually placed in the position of trying to hide the truth about the disorganized management of Harpo” and about Oprah’s
“tumultuous partnership” with her company’s chief operating officer, Jeffrey Jacobs. “Colleen devoted eight years of her life to Ms. Winfrey, but could no longer work in an environment of dishonesty and chaos.”

Infuriated at being publicly embarrassed, Oprah told reporters she would fight Raleigh’s suit to the bitter end. “There will be no settlement,” she said. Her lawyers tried to get the lawsuit dismissed, but managed only to require Raleigh’s lawyer to file amended complaints. This continued for months, until Oprah was hit with interrogatories requiring her to respond under oath to questions about her turbulent relationship with Jeffrey Jacobs and all the work she had made Colleen Raleigh do for Stedman Graham to promote him and his business with the Graham Williams Group and Athletes Against Drugs, and to help him promote his clients the American Double-Dutch League World Invitational Championship and the Volvo Tennis Tournament. After four more months of court pleadings, Oprah saw that it was in her best interest (and Stedman’s) to pay off her former employee and bind Colleen Raleigh for life with a confidentiality agreement that prevented her from ever talking or writing about her or Harpo. So, on March 29, 1996, Oprah settled the Raleigh lawsuit and put into place even more binding lifetime confidentiality agreements so that her employees—past, present, and future—could never talk or write about her. Now they were forbidden to take any candid photos of her, and banned from using cameras, camera phones, and tape recorders at work. These agreements were not simply for Harpo employees but for everyone within her realm—guests on her show, domestic workers, caterers, security guards, pilots, dog walkers, chauffeurs, upholsterers, the little man in Washington, D.C., who waxed her eyebrows, the physician in Maryland who gave her Botox shots, and the head of the Oprah Winfrey Leadership Academy in South Africa. When asked about her gag rule over her universe, Oprah said, “It’s all about trust,” not realizing it was all about her distrust.

She expected her friends to abide by her dictates on not photographing her without her permission, and most did, with the exception of Henry Louis Gates, Jr., known as “Skip,” who could not resist the temptation to sneak snapshots of her on his cell phone. “He likes to come into the faculty room and show us the pictures he’s secretly
taken of Oprah without her knowledge,” said a professor at Harvard University.

Professionally, 1994 was the worst year of Oprah’s life. She had driven her staff to exhaustion, and when her senior producers threatened to walk out because they no longer could endure the demands of Debra DiMaio for bigger and better ratings, she had to allow her dear friend to resign. By that point Oprah believed she had evolved beyond what Debra could deliver into a more exalted realm than a mere talk show host. She saw herself as a God-inspired missionary with a divine message to deliver. She no longer wanted to lead the trash pack. Instead, she sought the kind of respect that does not come from tabloid programming. With the exodus of DiMaio, Oprah decided to raise her show out of the gutter. She had read a report in
The Journal of Popular Culture
written by Vicki Abt, professor of sociology at Penn State, titled “The Shameless World of Phil, Sally, and Oprah.” Now encouraged by her senior producers, she decided to chase her glory with a softer focus.

Professor Abt was surprised by Oprah’s sudden about-face, but not filled with admiration. “I’m glad she has changed, but it’s ten years and $350 million later. I think a lot of what these people do is self-serving. They do the dirty deed and then they cry mea culpa.”

The year ended with a sucker punch when the December 1994 issue of
Redbook
hit the stands. The article, titled “Christmas at Oprah’s,” by former Harpo producer Dan Santow, looked like a frothy recollection of how Harpo employees honored their boss at Christmas and how she generously reciprocated. In between the lines was a searing X-ray of wretched excess and unimaginable extravagance in the workplace. Most damning was the fawning obeisance to the multi-millionaire boss and the slavish time and attention spent purchasing and presenting her gifts. This office ritual later evolved into the annual holiday show called “Oprah’s Favorite Things,” in which sponsors donated thousands of dollars’ worth of merchandise that Oprah selected throughout the year as one of her favorite things (e.g., HDTV refrigerators, diamond necklaces, BlackBerrys, digital video cameras, flat-screen televisions) and then gave to her audience, complete with a list of retail prices.