Oprah Unbound

After 25 years, Chicago’s Media Queen builds a bigger business and charitable empire, dabbles in politics, and strikes out for the West. Can $2.7 billion buy happiness?

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Winfrey salutes candidate Barack Obama after a 2007 rally in New Hampshire.

POLITICS

From the beginning of her television show in Chicago, Winfrey had refrained from making any political endorsements. She was above politics, she said. Even in 1996, when the Democratic Party held its national convention at Chicago’s United Center, only blocks from Winfrey’s Harpo Studios, she did not invite any politicians to appear on her show. Only John F. Kennedy Jr., who had never run for office, visited the show during the convention, and that was to promote his magazine, George.

In 2000, Winfrey departed from her own tradition and had both major-party presidential candidates, Al Gore and George W. Bush, on separate episodes of her show. Still, she did not endorse either candidate. That changed on May 1, 2007, when Winfrey appeared on the CNN show Larry King Live and announced that she was supporting the Illinois senator Barack Obama for president. “I haven’t [endorsed anyone] in the past because . . . I didn’t know anyone else well enough to say, ‘I believe in this person,’” Winfrey explained. She had met Obama and his wife, Michelle, in Chicago before his 2004 U.S. Senate bid. In 2005, the Obamas attended Winfrey’s Legends Ball, a white-tie affair celebrating African American women, at her Montecito home. In September of that year, says a friend of Michelle Obama, Winfrey and Barack shared a flight to Houston, where they checked in on Hurricane Katrina refugees. On the plane, the two bonded over their unusual “O” names, sharing people’s past suggestions—Joe O’Bama and Suzie Winfrey—for mainstreaming their names.

Winfrey’s endorsement was not entirely surprising. At her Legends Ball, she had jokingly suggested to Obama that her estate would be a great place for a fundraiser. And in October 2006, when both the Obamas appeared on her show, Winfrey publicly urged Barack to run for president, saying that if he did declare his candidacy, she would support him.

In an effort to draw a line between her show and her private opinion, Winfrey gave her endorsement on King’s show, rather than on her own. “My value to [Obama]—my support of him—is probably worth more than any other check I could write,” she said then. Although historically there is little evidence that celebrity endorsements draw voters to a candidate, Winfrey’s television show had produced some effect in a past election. On September 19, 2000, George W. Bush appeared on Winfrey’s show and talked about his decision to stop drinking and his love for his daughters. At the time, Bush trailed Al Gore by five points in a CNN-USA Today poll. The following week, the same poll showed Bush tied with Gore. Some news reports called it “the Oprah bounce.”

But for the 2008 election, Winfrey was not inviting the Obamas, or any other declared candidate, on her show. In an audio chat on her Web site in August 2007, Winfrey said it would be “disingenuous of me to be sitting up there interviewing other people . . . pretending to be objective.” Late in 2007, Winfrey hit the campaign trail with the Obamas, appearing at rallies in Iowa, New Hampshire, South Carolina, and California. The South Carolina rally had to be moved to a football stadium to accommodate the crowd of 29,000. Through Winfrey’s appearances alone, the Obama campaign estimated it garnered 10,000 new volunteers. The Washington Post wrote that most celebrity endorsements don’t matter, “but this one might.” And a study by the University of Maryland professors Craig Garthwaite and Timothy Moore concluded that Winfrey’s endorsement had resulted in a million votes for Obama in the primaries and caucuses.

Winfrey appeared to pay a price. According to a Gallup poll conducted in October 2007, shortly after her endorsement, her favorable rating fell by eight points, from 74 percent in January 2007 to 66 percent. Meanwhile, her unfavorable ranking rose by more than half, from 17 percent to 26 percent. It is unclear whether that trend will continue, but as Fortune once pointed out, if people decide not to trust Oprah, the person, the brand could quickly fizzle.

“With the Obama endorsement, I do think her image has been very politicized,” says Janice Peck, the author of The Age of Oprah. “On message boards for Oprah’s Web site, it used to just be adoring fans.

After the endorsement, you began to see some very negative responses. Now, it could be that these people are not her normal fans in the first place. But I do believe that her endorsement has caused some ripples among her fans.”

Part of the problem, Peck says, is that Winfrey has always presented herself as being above politics. “Then, suddenly, she got down into the muck of politics. So there are fans who are angry she endorsed anyone at all, Republicans who are angry she endorsed a Democrat, and Hillary Clinton supporters who are angry she didn’t endorse Hillary. Now, on her own Web site, I have started to see claims that she is a racist—that some fans feel she has endorsed Obama only because he is black. It’s incredible that she would see postings on her Web site accusing her of racism.”

On September 8, 2007, Winfrey hosted a spectacular fundraising party for Obama at Promised Land. More than 1,600 guests attended, with the ticket price starting at $2,300. Inside the gates, guests could mingle on the lawn, eat mini burgers and corn on the cob, and listen to a concert by Stevie Wonder. George Lucas was spotted; so was Sidney Poitier. Obama’s Chicago confidants Valerie Jarrett and John Rogers were present. No press was allowed, and most guests had to park in a lot eight miles away and be bused to the estate. On the Thursday before the event, signs were posted around Winfrey’s neighborhood, saying that the roads would be closed that Saturday.

“You are supposed to send a letter to the neighbors, not just post a sign,” says the Montecito resident J’Amy Brown, who admits that she was peeved about the lack of permits. After being invited and paying her $2,300, Brown was then disinvited, and her money was returned. Apparently the column she had written for the Santa Barbara Independent the week before, saying that she would be attending the party, was enough to get her nixed by Obama’s staff.

By 3 p.m. the day of the party, the Montecito roads were in gridlock. “We don’t have streets,” says Mindy Densen, who lives down the block from Winfrey. “We have tiny lanes. With all the buses, some of us worried about the safety of our kids and our dogs.” Still, Densen says, the Obama party was not an inconvenience for the neighborhood. She and her husband still held the annual block party that had been scheduled for the same day—although they did add cardboard cutouts of Obama and Winfrey “so all of us could feel we were part of the hoopla, too.” That starry night raised $3 million for Obama’s campaign.

On August 25th, Winfrey attended the Democratic National Convention in Denver. She kept a low profile during the week. After Obama’s acceptance speech, Winfrey told the reporters that she had “cried [her] eyelashes off” listening to the speech. Then on September 5th, just after the Republican convention ended, the Drudge Report, a conservative Internet site that covers politics, entertainment, and current events, posted a report that a disagreement was dividing the staff for Winfrey’s show. According to Drudge, half the producers were urging Winfrey to invite Sarah Palin, the governor of Alaska and the Republican vice-presidential candidate, to be a guest on the show but that Winfrey was refusing because of her support for Obama. The same day, Winfrey issued a denial. “The item in today’s Drudge Report is categorically untrue,” she wrote. “At the beginning of the Presidential campaign, when I decided that I was going to take my first public stance in support of a candidate, I made the decision not to use my show as a platform for any of the candidates.” Winfrey denied that there had been any discussion among her producers about inviting Palin.

Again, the message boards at Internet sites were filled with scornful posts about Winfrey, calling her unfair and racist. In an effort to force Winfrey to invite Palin, some started a petition; others cited equal-time obligations. But Winfrey, a political novice, had played her cards well. The Federal Communications Commission’s rules about equal time for candidates do not apply to news programs, interview shows, or documentaries in which the candidate is not the sole focus, so Winfrey was never obligated to give equal time to anyone.

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Photograph: AP Photo/Elise Amendola

This article appears in the December 2008 issue of Chicago Magazine.

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