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t’s hard to believe, but 19 years ago, in 1999, Donald Trump speculated that if he were to run for president one day, Oprah Winfrey would make an ideal running mate. At the time he was looking into the possibility of running as a third-party candidate, for the Reform Party. In interviews, he called Oprah “a wonderful woman, popular and brilliant.”

Last week, Oprah’s and Trump’s names were intertwined once more, but this time as potential electoral rivals. Oprah’s emotional speech at the Golden Globes, in which she defended the “under siege” press and promised a “new day” for young girls everywhere, led to hopeful speculation among supporters that she might one day run for president.

Oprah has a rags-to-riches story that captures the imagination. She was so poor growing up that her grandmother sewed dresses for her from potato sacks. By the time she reached high school, she was an honors student, voted most popular girl in the class, and earned a scholarship to Tennessee State University, where she majored in communication. Oprah began working as a news anchor in Tennessee and later in Baltimore. She got her big break when a prescient producer in Chicago recognized her talent and hired her to host a morning talk show, which was soon renamed The Oprah Winfrey Show. The rest is history.

Oprah is a hugely influential figure — and fabulously wealthy. At the age of 32 she made her first million, going on to become the first African-American woman billionaire, today worth $3 billion. Over the years, she’s donated $400 million to educational initiatives.

According to Joshua Cohen, a Democratic political strategist who was part of Barack Obama’s 2008 presidential campaign, voters want candidates, like Oprah, who inspire them. “She has what they want in a leader,” he said. “We have a leadership vacuum. More than anything else, what we need is a candidate with a story to tell, who has the ability to let others speak, who can give voice to the weak and unify the country. Trump is making a lot of Democrats think about who their candidate will be in 2020.”

After Oprah’s speech, those close to her didn’t confirm or deny that she would run for president. But if she did decide to run, there are several factors working in her favor. One is the short list of possible Democratic candidates. Joe Biden is popular and well known, but he’ll be 77 in 2020. Bernie Sanders will likewise be in his late 70s in the next campaign. Other possible candidates include senators Cory Booker, Elizabeth Warren, Kamala Harris, and Kirsten Gillibrand — all rising Democratic stars, but each of them lack name recognition on a national level, giving Oprah a definite edge.

“Oprah is an African-American woman who built herself up single-handedly, a media tycoon,” said Cohen, who now works in political consulting. “She’s exactly what is needed now, the antithesis to Trump.”

That said, Oprah has a lot to lose from a presidential run. Josh Kraushaar, managing editor of political coverage at the National Journal, says that Oprah risks losing her carefully calibrated media image in an electoral race. In politics, he says, opponents launch background checks that expose any negative detail in a candidate’s life. Oprah, he said, has a decent profile as a candidate, but that’s before all of her past comments, tax returns, and otherwise unknown dealings have been scrutinized.

But for Oprah to even be considered as a candidate means we are entering a new era in presidential politics. With a semi-celebrity already in office, the idea that a wealthy, popular media star may one day sit in the White House is no longer so strange. Does that mean political experience is passé? An Oprah run for president might answer that question, but not yet. By the end of the year, we should know more.

( (Excerpted from Mishpacha, Issue 694)