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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PROMISED LAND

In the summer of 2001, Winfrey bought a 42-acre private estate in Montecito. Although the property was still undergoing a three-year renovation, including the building of a 23,000-square-foot Georgian-style main house, she fell in love with it. The owners, Marlene and Robert Veloz (he is a Southern California industrialist; she, a philanthropist), who had been living in the 2,000-square-foot stone gatehouse until the main house was completed, agreed to sell it to her. The price was $50 million—according to The Los Angeles Times, one of the highest prices ever paid for a private residence in the United States.

The purchase of the Montecito property marked a turning point for Winfrey—it was a move appropriate for an established cultural icon. She would eventually play up the Martha Stewart similarity by printing photo spreads of the Montecito house in her shelter magazine, O at Home, which appeared in 2004 and is published quarterly. Like all landed gentry, Winfrey named her estate—she called it Promised Land.

Montecito (meaning “little woods”) is an exclusive unincorporated area outside Santa Barbara with a quaint storybook village. In 2007, Forbes ranked the area’s Zip Code the seventh most expensive in the country. And the estates of Montecito—with their views of both the ocean and the mountains—are highly prized. The property that Winfrey bought was originally developed in 1934 by a scion of the Libbey Owens Ford glass company. “It was a lovely old Montecito estate, with a lake and several ponds,” says J’Amy Brown, a local writer and the past president of the Montecito Association, a homeowners’ group dedicated to protecting the semirural character of the community. In 1998, the Velozes bought the property for $14 million and began renovations, starting with the construction of the stone gatehouse.

When Winfrey bought the property, she continued the renovations, making adjustments to suit her style. (The Velozes moved to a four-acre estate that had once belonged to Arianna Huffington and her former husband, Michael.) Winfrey’s fitness guru, Bob Greene, was named the property manager, and his cell-phone number was distributed to Winfrey’s Montecito neighbors. “If there was a problem with anything during construction, it was taken care of immediately,” says Brown. Dump trucks and concrete mixers were parked ten miles away, and when needed, they were called to the site by radio phone. “Around the same time, several other newcomers moved into the area, including the Chicago Beanie Baby mogul Ty Warner,” says Brown. “So we’ve seen some new things here, like security cameras pointed out to the road.”

After a year of renovations, Winfrey’s house was finished. Inside, it projects a genteel English air, with floral fabrics, upholstered chairs, and vases of full-blown roses. The acreage across the street from the house has been transformed into a meadow.

Montecito insiders say that Marlene Veloz shepherded Winfrey around her new hometown and introduced her to many of the people she socializes with today: Jelinda and Barry DeVorzon (she is the past president of the local film festival; he is a songwriter) and Margo and Jeffrey Barbakow (she is a philanthropist; he, the former chief executive officer of the Tenent Healthcare Corporation). Residents would often spot Winfrey in the village popping into stores and Trattoria Mollie. Another new presence in town: Stedman Graham, who had moved into the estate with Winfrey. “I often see Stedman more than Oprah,” says Mindy Densen, a Montecito neighbor. Evidently, warmer climates agree with Winfrey; in 2002, she purchased 102 acres in Maui for $8 million and hired the New York interior decorator Elissa Cullman to create an American farmhouse on the waterfront. (In 2006, Winfrey’s plans to add 63 acres of adjacent land fell through.) At the same time, she put her 85-acre ranch in Telluride, Colorado, and her 164-acre retreat in La Porte, Indiana, on the market, and both properties were later sold.

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

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