Inside Oprah’s Obama Party

The event people had been talking about for months finally came to be Saturday in Montecito. Talk show host Oprah Winfrey hosted more than 1,600 guests at her palatial estate Saturday afternoon in support of presidential candidate Barack Obama, bringing in more than $3 million for the Democratic hopeful.

Santa Barbara airport was reportedly packed with private jets, bringing in Hollywood celebrities, CEOs, and intellectuals traveling from near and far to the event, coming from such places as Michigan, Washington, D.C., Indiana, Boston, and Los Angeles. The highly publicized event, described by some as high-energy and full of hope and inspiration, turned out to be all it was promised to be for the guests who dropped $2,300 – the maximum one can give to a campaign-to attend. But just having the money wasn’t going to be enough to get in. It was a tough ticket to snag if you weren’t famous, involved in the Obama campaign, or friendly with either Obama or Winfrey.

Spotted celebrities included actors Forrest Whitaker, Ellen Pompeo, Sidney Poitier, Dennis Haysbert, former basketball players Bill Russell and Charles Oakley, music producer Russell Simmons, and director George Lucas. Oprah’s partner Stedman Graham was there, as was her close friend Gayle King. Some celebs like George Clooney and Will Smith, who had been rumored to have a ticket lined up to the event, weren’t spotted, but they could’ve had tickets to an even more exclusive after-party dinner.

There were only a handful of locals, according to some who were there, including Michael and Anne Towbes, realtor John Sener, author Patricia Bisch, painter Arden Rose, Beverly Jackson, Vicki Riskin, and public relations consultant Jonatha King. Other attendees included many from Obama’s campaign, like Julianna Smoot, his national finance director, who was no doubt pleased with the weekend’s earnings. Deborah Hayes, who had been the manager of all external communication strategies for Winfrey-owned Harpo Productions, and is currently the public affairs managing director for the Pew Foundations, was also there.

If you weren’t a celeb or VIP, Earl Warren Showgrounds was the place to park for the party. The check-in process was described as dignified by one guest. No cameras or recording devices were allowed. From there, guests were taken via Greyhound bus from Earl Warren Showgrounds to Oprah’s Montecito home, where they were unloaded walked through the front gate.

Guests were toward a grassy meadow down a wooded path, where servers on each side of the trail had wine, lemonade, and sparkling water waiting. The meadow extended from Winfrey’s house down a hill to the main stage. As guests approached the meadow, Winfrey could be seen with her party standing on the balcony to her house.

Those who followed invitation instructions for women to wear flat shoes proved to be wise, as the grounds weren’t easily walkable. Plus flat shoes made it easier to dance to Stevie Wonder, just a few weeks removed from a Santa Barbara Bowl concert, who was back in town and providing the on-stage entertainment for the evening. His daughter Aisha Morris also performed one song with her dad. Wonder told the crowd his band was playing for free that night. Bebe Winans closed the evening with a song and a poetic comedy act opened for Wonder.

Food for the evening was corn on the cob, mini hamburgers, chips and guacamole, and fruit as well as finger foods and drinks served throughout the party. Everything else was served from booths in the wooded area at the bottom of the hill.

According to attendees, rows and rows of green and white “Obama ’08” blankets had been laid out for guests to sit on for the concert and take home as a parting gift. There was also an area of tables and chairs where people could sit and watch, with two or three sectioned off for VIPs.

Before introducing Obama, Winfrey, who stated on Good Morning, America Monday morning that she hosted 1,657 people, told the crowd she hasn’t supported politics for many years because there hadn’t been anyone who had inspired her until Obama came along. She spoke “from her heart,” according to one attendee, about Obama’s authenticity, convictions, honesty, and commitment. She also told the crowd the $2,300 they each paid to attend was just the entry fee. “There is a lot of work to be done,” one person quoted her as saying. Winfrey brought Obama’s wife, Michelle, up on stage, giving her a hug and applauding her willingness and courage that comes along with being the wife of a presidential candidate.

Obama spoke for 20 to 30 minutes, touching once again on the idea of hope he spoke of earlier in the day at a public rally at Santa Barbara City College. After his speech, he and his wife took seats in the lawn and rocked the night away with the rest of the crowd, indulging anyone who approached him. Winfrey hung out with her man, Stedman Graham, on a blanket for much of the show, with security guards occupying the blankets on either side of them.