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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In early 2007, at the opening of the school Winfrey founded in South Africa

CHICAGO: HER PART-TIME KIND OF TOWN

When Winfrey started as the host of A.M. Chicago in January 1984, the half-hour program was considered a throwaway slot. It ran at 9 a.m. against The Phil Donahue Show, and Donahue, also based in Chicago, was dubbed “the titan” of daytime talk. With her close-cropped hair and bubbly enthusiasm, Winfrey modeled her show after Donahue’s—setting up on-air debates (Should this woman stay with this cheating man? Should children be spanked? Is it wrong to be a cross-dresser?). But while Donahue’s persona was cerebral, Winfrey came across as the gal next door, an image underscored by the frequent sightings of Winfrey riding the bus to the WLS-TV studio in the Loop. Within three months, she was beating Donahue in the Chicago market. By 1985, A.M. Chicago had been renamed The Oprah Winfrey Show and had been expanded to an hour. The following year, it went into national syndication, and Winfrey captured two daytime Emmys.

In the beginning, she would pad around the green room at the TV station in her stocking feet; backstage she would hover around the edge of conversations that celebrities—Jeremy Irons, Mel Gibson—were having, starstruck and tentative. “She was the kind of person who would go get her own soda and ask you if she could get you one, too,” recalls an early visitor. Over time, her hair got big (for a while bouffant), and her impact got bigger. As Fortune magazine wrote, “Oprah’s life is the essence of her brand.”

And that life was openly intertwined with Chicago. Winfrey ate at the modest Papa Milano’s on State Street. In 1989, with the Lettuce Entertain You mogul Rich Melman, she opened a restaurant, The Eccentric, and would often pop in to say hello to customers or to eat some of “Oprah’s mashed potatoes,” a popular menu item. She started dating Stedman Graham, the chief executive officer of his own marketing, management, and consulting firm and the former boyfriend of the local television news anchor Robin Robinson. By 1992, Winfrey and Graham were engaged and talking about wedding dates. In her quest for fitness, she could be seen running along the lakefront in the early morning or working out at the East Bank Club. Even when she wanted some free time, she didn’t go far. Weekends were spent outside La Porte, Indiana, on her 164-acre estate anchored by a French farmhouse. The property was equipped with a ten-stall horse barn, a helicopter pad, and roaming llamas. In the summer, Winfrey ran on back roads and waved to neighbors.

But slowly, her focus changed. That started with her television show. “It’s time to move on from ‘we are dysfunctional’ to ‘what are we going to do about it?’” Winfrey told The Boston Herald in 1994. Her show changed directions, emphasizing the positive, healing, and self-fulfillment. “Her rise mirrors the dramatic growth of therapy as an institution in American culture,” says Janice Peck, an associate professor in the school of journalism and mass communications at the University of Colorado and the author of The Age of Oprah: Cultural Icon for the Neoliberal Era (Paradigm Publishers, 2008), a book about Winfrey’s widespread influence. “The forms of spirituality she has embraced and the emphasis on personal responsibility—these can be seen as an element of American history. Oprah does reflect her times.”

That change moved Winfrey’s show away from what was then a proliferation of trashy TV talk shows (with hosts such as Jenny Jones, Jerry Springer, and Ricki Lake), and when the scandal of a former Jenny Jones guest murdering another guest exploded in 1995, Winfrey was already far above the fray. In 1996, she started her book club, which played a seminal role in elevating Winfrey to iconic status. Most of her choices became instant bestsellers. Two years later, she introduced an occasional segment on her show, Change Your Life TV. She performed the theme song herself and conferred with self-help gurus such as the psychologist Dr. Phil McGraw, the financial adviser Suze Orman, the relationship mentor John Gray, and the spiritual writer Gary Zukav. Remembering Your Spirit, a five-minute segment about finding one’s center, ended each episode. Journaling and the search for “new truths” were encouraged, but for the first time, Winfrey’s ratings dropped. Two months later, she dialed back Change Your Life TV, cutting those themed shows by almost a third.

Winfrey’s own center seemed to change, too. She wasn’t seen riding the bus anymore. In 1995, she and Melman shut down The Eccentric. The relationship with Graham continued, but a wedding never materialized. In 1998, Winfrey told this reporter: “I see no reason to get married if I’m not going to have children. And I’m not. I could not do what I do as well as I’m doing it and have a child. Impossible.” Winfrey’s time in Chicago now centers on the shooting schedule for her show: She flies in from California on Monday night; works at Harpo on Tuesday, Wednesday, and Thursday; and then flies out Thursday evening.

The visitor who remembers Winfrey from the old days, asking people backstage if she could get them a soda, met with her again a few years ago. “Things had changed,” he recalls. “I don’t think the queen of England is treated with such deference and formality.”

In Chicago, Winfrey is protected and hidden from random view. Since 1984, she has lived in Water Tower Place, in what is now a 15,000-square-foot duplex. Some residents in the building say they rarely see her on the elevators. Recently, she bought a 5,000-square-foot co-op on East Lake Shore Drive, one of the most exclusive addresses in the city. But she abandoned the idea of downsizing her Chicago duplex and moving there when she realized that residents from nearby apartments could see into her windows. That apartment has been sold.

When she isn’t here, Winfrey is spending time at her Montecito retreat—“We know she is here when we see her jet,” says a neighbor—or at her 102-acre home in Maui. She is visiting the Oprah Winfrey Leadership Academy for Girls that she started in South Africa in 2007 or touring Italy with a group of close friends that includes the writer and director Tyler Perry and her longtime pal Gayle King, an editor-at-large for O, The Oprah Magazine. The air around Winfrey now is rarefied; her private life has a profile so low that only big money can sustain it—in her case, that profile remains very low.

Photograph: AP Photo/Denis Farrell

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

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