Oprah (68 page)

Before the 2008 presidential election, Oprah was so determined to preserve her platform for Obama that when Bill Clinton returned to her show on September 4, 2007, to promote his second book,
Giving,
she made a point of telling viewers that he had called her himself, asking to appear. Months later the former president shrugged off Oprah’s lack of support for his wife. “Oprah is from Chicago,” Clinton said. “She was never going to be for anybody but Obama.”

The timing of Clinton’s second appearance on Oprah’s show was politically sensitive, because everyone knew that four days later she was hosting a huge fund-raiser for Obama at “The Promised Land,” her forty-two-acre estate in Montecito. The event, planned to accommodate
at least sixteen hundred people paying $2,300 apiece, was trumpeted as one of the largest political fund-raisers in history. One late-night comic joked, “Oprah’s fund-raiser is projected to raise three million dollars; two million of which is to come from the ‘Dunk Stedman’ booth.”

Oprah’s fund-raiser had been announced in July, and people across the country scrambled to buy tickets as much to support Obama as to see Oprah’s $50 million mansion, with its man-made lake and rolling meadows. The event received wide coverage around the world and, according to Oprah, it “was no small thing for me [to open the gates of my estate]….I really do feel that this place is God’s gift to me. It is a very, very special place….There are going to be some serious restrictions and requirements to get in there.”

She insisted that no one be allowed inside the twenty-three-thousand-square-foot mansion, so the event was staged outside on a sunny Saturday afternoon with Stevie Wonder (an Obama favorite) performing. More than sixteen hundred people attended, sitting on apple green blankets that Oprah had commissioned with “Obama 08” woven in the corner. Tents filled with tables of food and drink (mini hamburgers and “electric” lemonade spiked with vodka) dotted the landscaped lawns, where squadrons of waiters scampered about with silver trays. No press was allowed, and all guests were wanded by security guards after being relieved of cameras and recording devices. With the exception of a few VIPs, no one was allowed to drive into the premises, so everyone had to assemble ten miles away and be transported by shuttle buses. Celebrities in the majority African American crowd included Whoopi Goldberg, Sidney Poitier, Ernie Banks, Bill Russell, Jimmy Connors, Linda Evans, Lou Gossett, Jr., Cicely Tyson, Forest Whitaker, Tyler Perry, Chris Rock, Cindy Crawford, George Lucas, and Kenneth “Babyface” Edmonds.

After the picnic, Oprah hosted a dinner party for two hundred in a huge tent with crystal chandeliers. “It was a magical night that I will never forget,” said Valerie Jarrett, a close Chicago friend of the Obamas and now senior advisor to the president.

“Marred only by one diva moment,” recalled another Chicago guest. “When Cindy Moelis and her husband, Bob Rivkin, arrived with the Obamas—Cindy is one of Michelle Obama’s best friends—Oprah was
very ungracious. She invited the Obamas inside, but directed Cindy and Bob to wait outside, where they sat on one of the unreserved green blankets. The meadow soon filled up….Oprah and Stedman came out and sat on a reserved blanket in front of Cindy and Bob, an arm’s length away. One of Oprah’s bodyguards came over and told Cindy they had to move. Cindy asked why, pointing out there was no room, and Stevie Wonder was about to perform. Another guard came over and told Bob they had to move or leave. Bob said they had come with the Obamas and they were not moving or leaving. This all happened within earshot of everyone on adjacent blankets, who were watching, except for Oprah and Stedman, who sat with their backs to Cindy and Bob as if they didn’t know what was going on. One would think a hostess would have her security guards stand down to avoid escalating an unpleasant situation. But no. The guards then took out notebooks and wrote down their names, repeatedly asking for the spelling of
Moelis
as if to loudly embarrass them into leaving. They stayed for the performance….The event was fantastic, except for Oprah making two people feel very unwelcome.”

Such moments become indelible because some people expected Oprah to be at all times what she appeared to be on the air—a woman of enveloping warmth, charm, and affability.

“She was fabulous when she took the microphone and introduced Barack,” said another guest. “She was passionate, gracious, and intoxicating in her remarks.”

She began by saying that her home in Montecito was sacred to her, explaining that she called it “The Promised Land” because she was living Martin Luther King’s dream. For that reason she said she would not open it for just any event. “This is where Stedman and I lead our private life,” she said. “I haven’t participated in politics because no one inspired me until now….After all of my years in business I don’t trust many people, but I have learned to trust my own instincts….I believe we have a man here who can make a difference and bring dignity back to the people of the United States….I believe in destiny. If someone has a calling, there is nothing that can stop that destiny.” For that reason she said she had committed herself totally to Obama and was willing to take whatever the media hurled at her for doing so.
She also mentioned the $2,300 price tag for the event and said that no one, “not even my best friend, Gayle,” got in without paying.

Oprah understood her worth to Obama. When she talked about her endorsement on
Larry King Live,
she said, “I think my value to him, my support of him, is probably worth more than any check that I could write.” Federal Election Commission records show that she wrote only one—for $2,300. Yet she raised more than $3 million for him in California, and in Chicago some of her employees provided additional funds:

After endorsing Obama, Oprah experienced repercussions from viewers, who lashed out on her message boards:

“Oprah is a traitor!!!!”

“In bad taste.”

“I will never watch your show again.”

In 2008 the Harris poll announced that Ellen DeGeneres had beaten Oprah as America’s Favorite TV Personality, a position Oprah had held for the previous five years.

Twelve weeks after her California fund-raiser, Oprah hit the road for Obama, flying with Gayle to Iowa to speak in Des Moines (attendance 18,500) and Cedar Rapids (attendance 10,000) before being whisked off to Columbia, South Carolina (attendance 30,000), and Manchester, New Hampshire (attendance 8,500). In each city, the media stands were crammed with television cameras from around the world waiting to record her first campaign utterances.

Initially she seemed awkward, saying she felt she had stepped out of her pew, as she again referenced
The Autobiography of Miss Jane Pittman
and how the enslaved woman was searching for “the one” who would lead her people to freedom. “Well, I do believe in ’08 I have found the answer to Miss Pittman’s question. I have fooo-uu-nd the answer! It is the same question that our nation is asking, ‘Are you the one? Are you the one?’ I’m here to tell y’all, he is the one. He is the one….Barack Obama!”

By the fall, Hillary and Obama had sprinted ahead of the six other Democratic candidates, with Hillary enjoying the overwhelming support of women, while Obama captured the enthusiasm of the highly educated and the antiwar activists. He won the Iowa caucuses; she won the New Hampshire primary. On Super Tuesday she won 836 delegates; he won 845. Their neck-and-neck race continued until June 7, 2008, when Hillary officially ended her campaign and eloquently endorsed him.

During the early months of the campaign, Oprah had been alone in carrying the high-wattage celebrity torch for Obama, but on January 27, 2008, Caroline Kennedy stepped forward to announce her endorsement. In a
New York Times
op-ed titled “A President Like My
Father,” the daughter of John F. Kennedy wrote, “I have never had a president who inspired me the way people tell me that my father inspired them. But for the first time, I believe I have found the man who could be that president—not just for me, but for a new generation of Americans.” With Caroline Kennedy came her cousin Maria Shriver, and their uncle Senator Ted Kennedy, whose endorsement galvanized the campaign and shook the timbers of support for Hillary Clinton, especially among African Americans, who began to see that Barack Obama might actually have a fighting chance.

By the time Oprah appeared at UCLA’s Pauley Pavilion flanked by Caroline Kennedy, Maria Shriver, and Michelle Obama, she felt emboldened enough to address her critics:

“After Iowa, there were some women who had the nerve to say to me, ‘How could you, Oprah, how could you?’ ” she said, imitating a nasal twang. “ ‘You’re a traitor to your gender.’ The truth is, I’m a free woman. I am a free woman.” She repeated this three times. “Being free means you get to think for yourself and you get to decide for yourself what to do. So I say I am not a traitor. I am just following my own truth, and that truth has led me to Barack Obama.” She mocked women who declared, “I’m a woman; I have to vote for a woman.” She fired up the crowd. “As free women, you have the right to change your mind. You’re not a traitor because you believe and see a better way.”

At the end of that rally Michelle Obama told the rapt crowd, “I want you to leave here and envision Barack Obama taking the oath of office.”

So Oprah, who believed in the tenets of
The Secret,
a book she had pressed on Obama, returned home and created a vision board (see it, believe it, achieve it). She put Obama’s picture in the middle of the board, alongside a picture of the dress she wanted to wear to his inauguration. Then she began visualizing the success she wanted. By the time Obama secured the Democratic nomination in August, she was fully convinced that he was destiny’s child and would be elected president.

“I’m very happy that I made the decision early last year to come out for him….I decided early on that even if I lost every sponsor on the show—there’s a wonderful Bible passage [Matthew 16:26] that
says, ‘What does it do for a man to gain the world and lose his soul?’ If I had not come out for Barack Obama when I did, I know I would have lost a piece of my soul.”

On election night, Oprah, in a bright green dress with a suggestion of cleavage, joined the joyous throng of 125,000 people in Grant Park to cheer Chicago’s favorite son as the first man of color to be elected president of the United States. With tears streaming down her face she rejoiced, standing on the right side of history and knowing that she just may have had a role in shaping it.

“My job was to make people, or allow people, to be introduced to Obama who might not have been at the time,” she said. “I wanted him elected, and I think I did that.”

I
 REMEMBER
Oprah standing in the control room watching Phil Donahue toward the end of his run and shaking her head,” recalled a former Harpo employee. “She said, ‘If I ever stay that long, kick my ass out of here.’ Of course, that’ll never happen because she’ll never give up her show. She can’t…she needs to be on television. It’s her oxygen.”

Most people assumed that it would take a wrecking crew with tasers and stun guns to get Oprah to retire, but on November 20, 2009, she announced she was stopping her show after twenty-five years—when her contract expired in September 2011.

“This show has been my life,” she told her viewers with trembling lips, “and I love it enough to know when it’s time to say goodbye.”

Those words sent an “Oh, my God” shudder across the country and triggered Code Orange distress throughout the television industry. Oprah’s departure from four o’clock in the afternoon would crater a hole in daytime broadcasting and deprive local stations, especially those owned and operated by ABC, of a gigantic ratings lead-in to their evening news hours. The financial ramifications were potentially enormous.

From the next day’s headlines it seemed as if Chicken Little was right: the sky had fallen. Oprah’s announcement made the front pages of most newspapers, the cover of
People,
and the evening news broadcasts, and prompted a tidal wave of commentary, most of which praised her for hanging up her gloves before she risked getting knocked out by dwindling network audiences and flaccid ratings.

Alessandra Stanley applauded her in
The New York Times
for practicing “The Fine Art of Quitting While She’s Ahead,” and Gail Collins wrote a column about “Putting the Fond in Farewell.” The
Los Angeles Times
mourned “Afternoons Without Oprah,” and
The Wall Street Journal
wondered what her departure would mean for the economic future of Chicago.

Oprah said she planned to concentrate on OWN (Oprah Winfrey
Network) in partnership with Discovery Communications. The debut of OWN, announced in 2008, was originally scheduled for 2009. Now it will be sometime in 2011. Once launched, Oprah’s network will replace the Discovery Health Channel, which is available in 74 million homes.
The Oprah Winfrey Show,
in 2008–2009, before the nation switched to a digital system, reached approximately 110 million homes. In its current incarnation, the show is watched by around 7 million people each day. There is little doubt that switching to OWN will dramatically lower her viewership.

OWN is based in Los Angeles, and soon after her announcement, Oprah was quoted as saying she wanted to divest her real estate in Chicago “as soon as possible,” adding, “Why would anyone stay in Chicago? It’s freezing here, and I have a mansion in Montecito that I haven’t been able to enjoy.”

While the national media mourned the departure of daytime’s Goliath, the Davids of Chicago grabbed their slingshots. “[H]er announcement spurs a question: Does it matter?” asked the
Tribune
’s Rick Kogan. “Over the years she has become, with some justification, increasingly isolated, distrustful of all but a close circle of friends and associates, and remote…” With tongue in cheek, the
Trib
’s media critic, Phil Rosenthal, told readers: “Deal with it however you see fit. Maybe ask yourself: What would Oprah do? Then call your best friend Gayle to commiserate.”

Chicago’s mayor, Richard Daley, was furious at the tone taken by the city’s media and blamed them for driving Oprah out of town. At her request, he had closed part of Michigan Avenue for her season’s opening show in September 2009, which lured twenty thousand fans, snarling traffic in the middle of the city’s busiest street. The havoc did not go unnoticed by reporters, some of whom saw it as just one more example of Oprah’s hubris.

“That became a big rhubarb in the Chicago press—beat up Oprah,” said Mayor Daley. “So you keep kicking people, people will leave, simple as that.”

She returned the mayor’s favor and support by flying to Copenhagen to join him and the president and First Lady to lobby the International Olympic Committee to bring the 2016 games to Chicago,
which had spent $60 million on its presentation. When the IOC knocked Chicago out of the competition almost immediately and gave the nod to Rio de Janeiro instead, Oprah, Mayor Daley, and the Obamas were made to look like losers in the Chicago press.

The media maelstrom over her retirement continued for days. “Why is she quitting?” “What will she do next?” “Who will replace her?” Then dire predictions about her health flooded the Internet, along with photos suggesting her weight would lead to debilitating diabetes and an inevitable heart attack. The
National Enquirer
ran a cover of her looking haggard and bloated with a headline that blared: “Oprah’s Booze & Drug Binges! Fed Up Stedman Walks Out—for Good! She’ll Pay $150 Million to Buy His Silence.” This prompted the always cheeky David Letterman to announce: “Top Ten Signs Oprah Doesn’t Care Anymore.” The number one sign: “Her last three guests were Johnnie Walker, Jim Beam, and José Cuervo.”

It began to look as if her withdrawal from network television and her perceived loss of influence was turning her into a target, after years of reverential treatment. However, as she was being depicted as a dipsomaniac and dismissed by polls that (supposedly) showed her dwindling popularity, Oprah showed she should never be underestimated, pulling off a coup that burnished her luster on the world stage. She took her cameras to the White House for an intimate conversation with the Obamas as they prepared to spend their first Christmas as president and First Lady. Her hour-long prime-time special gave ABC the evening’s most watched entertainment program (11.8 million) and showed that at the age of fifty-five, Oprah Winfrey is not about to relinquish her crown as the queen of talk show television.

Instead, she is going to attempt to reinvent herself with her own network (“All Oprah all the time,” said one critic) and present on cable what she presented so effectively in her magazine: her philosophy of life with its perplexing mix of crass materialism and uplifting spirituality.

Some critics tut-tutted that her fans will not follow her to cable. Others speculated that OWN will never get off the ground, citing its start-up problems with scheduling, the fact that three CEOs have already been hired and fired, and the head of programming deposed, all of which has delayed the launch date several times. But Oprah had
already embarked upon her next career, and
The New Yorker
’s media critic predicted unbounded success. “Oprah is going to a growing enterprise,” said Ken Auletta. “She’s leaving a listing ship and getting on a rocket ship.”

She was also taking her halo to Hollywood, where she would reign supreme among the celebrities she adored. The town had first fired her fantasies as a young girl when she toured the Walk of Fame in front of Grauman’s Chinese Theatre. After that trip she returned to her father’s house in Nashville and told him she was going to be a star.

“Daddy, I got down on my knees there and ran my hand along all those stars on the street, and I said to myself, ‘One day I’m going to put my own star among those stars,’ ” recalled Vernon Winfrey. He knew then there was no stopping his daughter.

Now, decades later, the pilot light that fired her ambitions since childhood still flames, and for Oprah her work and the applause that comes from it fill her soul, giving her her greatest pleasure in life. Consequently, she will never retire. Without children and grandchildren, it seems as if she will fill her later years with the rewards of work. Yes, she has slowed down a bit and often seems fatigued, occasionally appearing listless on her show, the one hour a day when she had sparkled in the past. During the last year her producers began booking more segments to move it along at a faster pace so everyone, including the host, would stay engaged.

As she gets older, Oprah no longer expends the energy necessary to stay in shape, and she remains seventy-five pounds overweight, sagging into her mother’s genes after years of swearing to fight heredity. The responsibility of her $40 million school in South Africa has also weighed on her, especially as the sex scandals involving a dorm matron and several students dragged through the courts. The publicity surrounding the sordid case was demoralizing, and prompted some to question how anyone, even with Oprah’s vast resources, could take care of three hundred children eighty-seven hundred miles away. Still, she remains committed to her “girls” and flies to South Africa at least once a year. But even in her own private jet the seventeen-hour trip takes its toll.

Despite a setback in her show’s ratings, a dip in her magazine’s circulation, and a couple of chinks in the armor of her public image, Oprah remains the most influential woman of her generation. She has always lived on the ascent, and even as she ages, she continues aiming upward.

She has dominated her era by reaching uncommon and unexpected heights, and in doing so, she has become an icon, especially to women. For she has broken through all the barriers that once held them back, and her life story inspires others because she has never stopped pushing ahead. She has remained driven, and in all likelihood will continue to remain so to the end of her days because she has always embraced the poetry of Robert Browning, who wrote that “a man’s reach should exceed his grasp, or what’s a heaven for?”