The Deal Donald Trump Couldn't Close

The veep he's said he wants has instead endorsed Hillary Clinton

Donald Trump once said Oprah would be a fantastic VP choice, but now she's backing Hillary Clinton. (Photo by Kevin Winter/Getty Images for NAACP Image Awards)

Way back in 1999, when Donald Trump was toying with the idea of a presidential run, he was asked who would be a good vice president on a Trump ticket and cited Oprah Winfrey, calling her “very special.” Just last year, he repeated that choice, saying that together, the two would win “easily.” It would be the showman’s dream. Celebrity meets celebrity.

Well,  Oprah Winfrey is taken now. She has endorsed Hillary Clinton, and that, as Trump would say, is huge. Next to her, other Clinton celebrity endorsers, including George Clooney, look like chopped liver.

Like Trump, Winfrey is skilled at mixing politics with business — her business. She announced the endorsement at a premiere of her new OWN network show, “Greenleaf.” She said to Entertainment Tonight: "Regardless of your politics, it’s a seminal moment for women,"   and echoed Clinton’s slogan when she added, “I’m with her.”

Will her endorsement bridge the divide between the white feminists of her generation and the African-American women who worked tirelessly for Barack Obama, loved Michelle Obama and carried the family into the White House on their electoral shoulders? If anybody can bridge that divide, it may be Winfrey, who has a few scars from that particular war.

It was electric in 2007 in Williams-Brice Stadium in Columbia, S.C., when Winfrey transferred her star power to the Obama campaign, appearing with Obama, then a senator, who acknowledged which “O” the crowd estimated at 30,000 had really come to see. It was a decision that was criticized at the time by some fans and viewers who were "Team Hillary" all the way and accused the talk show host/mogul of choosing color over gender.

When African-American women look into the mirror in the morning, they aren’t black one day and a woman the next. But the “whose side are you on” question has been one African-American women have routinely been asked.

Winfrey's endorsement in the 2008 race started a rehash of a conversation that was an echo of abolitionist/suffragist Sojourner Truth’s 1851 lament: “Ain’t I a Woman?” on the special trials of being black and a woman. It has extended through the modern-day feminist movement from Betty Friedan and “Lean In” and doubts about whether some leaders were as inclusive as they needed to be or if enough credit was given to women of color.

The divide spilled out into editorial pages when it was Clinton vs. Obama, with Gloria Steinem arguing for Clinton , and noting that black men got the vote before white women. Others urged her to take a more realistic view of the racial history of this country.

By November 2008, many white female Democrats, despite PUMA (Party Unity My Ass) loyalty, returned to the party fold though overall, Obama lost the majority of white women’s vote in 2008 and 2012. Nevertheless, he was elected twice.

The alliance has not always been an easy one, with Michelle Obama, for example, coming in for criticism from some white feminists puzzled by   choices  like describing herself as "mom-in-chief." It fell to black women to explain that spending time raising your own children and not someone else's can be a revolutionary choice.

Now the African-American women who were the backbone of the Obama coalition, who turned out in numbers greater than any other demographic considering their share of the electorate, are needed for Clinton to win in November.

Winfrey could be the key to getting them to the polls — and convincing them to bring their friends, neighbors, church mates and partners. She’s still popular with the rest of the electorate, as well.

Witness her queenly appearance spot on last Sunday’s Tony Awards. Host James Corden paid a tribute and the show “The Color Purple,” which she helped bring to Broadway in several incarnations, won awards for best revival of a musical and best actress in a musical for its star Cynthia Erivo.

Oprah did that smiling and crying thing as only she can.

If she takes that show on the road from now until November, with some appearances with Clinton, a bit of the “Oprah” touch may rub off on a candidate who knows the details stone cold but has been accused of being light on that undefinable “something.”

Donald Trump certainly knows it when he sees it, which is why he may be regretting one deal he could not close.

Roll Call columnist  Mary C. Curtis  has worked at The New York Times, The Baltimore Sun and The Charlotte Observer. Follow her on Twitter  @mcurtisnc3 .

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