Home Celebrity Oprah’s Politically Opposite Billionaire Republican Pal, Harold Simmons, Is Dead

Harold Simmons, the right wing Dallas billionaire who underwrote both the John Kerry Swift Boat effort and the anti-Obama Bill Ayers campaign, is dead at age 82. I wrote about him in 2008 because it turned out that Simmons and his wife were best pals with Oprah Winfrey. Huh? Yes. Simmons donated $5 million to Oprah’s South African Leadership Academy for young women. Winfrey and the Simmonses are neighbors in the extremely posh Montecito, California. How Oprah managed this friendship tells a lot about how engages power, period. Simmons, — a self made billionaire from savvy investing– leaves behind an eponymous charitable foundation now run by his daughters. The Harold Simmons Foundation seems to have taken a sharp turn to the left. The daughters are to be commended. Condolences on their loss.

I wrote in 2008:

Winfrey is very close friends with Dallas billionaire named Harold Simmons, a leading Republican donor and supporter of John McCain.

This past August it was revealed that Simmons was the single donor to a 527 committee called American Issues Project. Its only issue: to run ads linking Obama to William Ayers, the political activist who was once part of the Weather Underground. Simmons paid $2.9 million to try and make Ayers the Obama campaign’s “Swift Boat,” an issue that might have sidelined permanently the Illinois senator’s chances and advance John McCain — Simmons’s candidate — to the White House.

Nevertheless, Winfrey has cultivated her friendship with Simmons on many social fronts since 2001, resulting in his being second only to her in donating funds to her Leadership Academy in Johannesburg, South Africa.

According to the 2006 federal tax filing for the Oprah Winfrey Operating Fund, Winfrey accepted a $1 million donation to the school from Simmons. That amount, The Dallas Morning News reported in 2007, was only part of a $5 million pledge to the Academy. Simmons is considered Dallas’s leading philanthropist to worthy causes. In this case, though, it might have been unnecessary, since Winfrey herself has donated over $60 million to the school.

It’s not like Simmons is a new Republican donor. He gave over $100,000 in the 2007-2008 election cycle to Republican candidates, separate from his Ayers campaign. He has always been an active Republican. In 2004 he was a major donor to the Swift Boat Veterans, the group credited with destroying the campaign of John Kerry for president.

Winfrey has long been close friends with Simmons and his wife Annette. She’s their neighbor in Montecito, California, having bought the estate next to them in 2001. As recently as two weeks ago, Oprah mentioned the couple on her show during a telephone discussion of the Montecito fires with another neighbor, actor Rob Lowe.

(Winfrey was not available for comment, according to her representative. Simmons, who doesn’t have a press representative, did not return our call.)

The Dallas Morning News—thanks to the dogged byline of Alan Peppard — is full of stories over the years documenting Oprah’s friendship with the Simmonses. They are often at each others’ homes and parties. When Oprah’s significant other, Stedman Graham, spoke to a group in Dallas, it was noted that he dined with the Simmonses. In April, 2006 — two years after the Swift Boat scandal was revealed — Oprah sent a camera crew to a Dallas luncheon hosted by Annette Simmons showcasing the thousands of tulip bulbs surrounding the lake on her property.

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