Democrats on Oprah 2020: It's not crazy and she could win, but ...
Posted January 8, 2018 3:16 p.m. EST
WASHINGTON (CNN) — The day after Oprah Winfrey delivered a speech that thrust her into the conversation about the 2020 presidential race, Democratic strategists and activists largely agree: It's not crazy. And she could win.
First, though, Winfrey would have to answer huge questions. Among them: Where does she stand on the issues? Is she willing to sacrifice her personal popularity and face scrutiny over how her business empire has operated?
The television star and self-made billionaire addressed the "#MeToo" moment and promised that "a new day is on the horizon" during a Golden Globes award acceptance speech Sunday night. The speech struck a chord, drawing comparisons to then-Illinois state senator Barack Obama's 2004 Democratic National Convention speech, which launched him toward the presidency four years later.
Sunday night, when her longtime partner, Stedman Graham, was asked by a Los Angeles Times reporter about Winfrey running in 2020, he said she "would absolutely do it." On Monday, two Winfrey friends told CNN she is "actively thinking" about a run for president.
Democrats across the country said that in Winfrey they see some of the qualities they're seeking in a 2020 nominee.
"Here's the thing, I think, with Oprah with women that are in their 30s, 40s and 50s: She was the first kind of serious media personality who on a regular basis told our stories. She was in our living rooms, giving validity to our stories," said Jane Kleeb, the Nebraska Democratic Party chairwoman.
A Winfrey campaign for president would drastically alter an early playing field on which Sen. Bernie Sanders of Vermont, former Vice President Joe Biden and Sen. Elizabeth Warren of Massachusetts are the biggest players for the Democratic nomination -- with Sens. Cory Booker of New Jersey, Kamala Harris of California and Kirsten Gillibrand of New York also getting serious attention.
Several Democratic strategists argued that Winfrey is one of the few people on Earth who could pull the focus of national media away from Trump in the heat of a presidential campaign -- or "out-Trump Trump," as one put it. Others cast Winfrey as an antidote of sorts to Trump's brand of politics.
"I slept on it and came to the conclusion that the Oprah thing isn't that crazy," tweeted Dan Pfeiffer, a longtime top aide to former President Barack Obama. "I don't know if Oprah would be a good president, but she would definitely be a better president than Trump."
"Oprah is really everything that Trump pretends to be -- successful, self-made, generous, charitable, beloved and the list goes on," said Democratic strategist Jesse Ferguson.
"She would be a viable candidate not because of her celebrity but in spite of it," he added. "She would be a viable candidate because of all she's accomplished, because of all she's done for people and because of what she stands for, so it's very different from Trump."
Oprah in the early states
Winfrey proved her broad appeal to Democratic voters in 2007, when she barnstormed Iowa, New Hampshire and South Carolina for Obama -- the first presidential candidate she'd ever publicly endorsed.
"I remember like it was yesterday. I sat at home watching it on television and sulking," said Jerry Crawford, a longtime veteran of Iowa presidential politics who was the Midwest co-chair of Hillary Clinton's 2008 campaign.
Tens of thousands of people showed up on cold, snowy days in Des Moines and Cedar Rapids, Iowa, and then in Manchester, New Hampshire. Then 30,000 packed into a football stadium in Columbia, South Carolina, to hear Winfrey and Obama.
"Oprah is as good in a mega-rally-type setting as she is in intimate conversational settings," Crawford said. "It's not unusual at the presidential candidate level to find people who are good at one or the other. She can do both."
"If she actually got into this race, it's pretty hard to see how she wouldn't be one of three at the end of the day coming out of Iowa," Crawford said.
There are major questions that would confront Winfrey if she were to enter the pressure cooker of national politics, and caveats that apply when considering her as a 2020 prospect.
Will Democratic voters be hungry for a progressive champion relentlessly focused on the issues, or for a healer who can move the country past the Trump era's bitter and personal politics?
And where does Winfrey stand on the issues that will define the Democratic nominating contest?
She would also have to accept the brutal toll presidential campaigns take on candidates' personal popularity. Clinton's favorability rating dropped from the low 60s when she departed as Obama's secretary of state into the low 40s toward the conclusion of the 2016 race, per Gallup polls.
There's also the reality that Clinton was pilloried as focusing too much on identity politics -- and, several Democratic strategists noted, Winfrey's Sunday night speech was all about identity politics. It's not clear whether her appeal would translate to the suburban and rural voters who have fled the Democratic Party in recent elections.
Like Trump, Winfrey would also face questions about her business, which is similar to Trump's in that licensing and entertainment are core components. Would she release her tax returns? Could she answer for lawsuits?
House Minority Leader Nancy Pelosi wasn't immediately sold on a Winfrey run.
"I think one of the arguments for Oprah, arguments for Oprah, is 45. I think one of the arguments against Oprah is 45," Pelosi told reporters Monday, speaking of Trump as the 45th president.
Where is she on the issues?
For Winfrey, a revered figure for decades who has never courted public brawls like Trump, that scrutiny would be new.
Those complications are why some Democrats believe the buzz about a Winfrey presidential run that followed her Golden Globes speech will pass in time.
"I will tell you what I think about Oprah's chance of being the Democratic nominee in 2020 when you tell me where Oprah is on single payer and what her plan is to pay for it; what her immigration reform proposal looks like and what kind of border security it includes; and which elements of the Trump tax plan she'd roll back and which ones she would leave in place," one veteran Democratic strategist said, speaking on the condition of anonymity.
Asked whether the strategist's name could be used, the Democrat said no, explaining: "I don't need Oprah mad at me!"
Winfrey has said before that she's voted for Republicans as well as Democrats -- which would raise questions about which conservative policies she has supported.
"There are a lot of practical things she'll have to figure out in terms of her positions and what her general message is going to be," said Brad Anderson, who was Obama's Iowa director in 2012. "For example, I don't know what her position is on health care or the minimum wage. But she does have a healing personality. Given that, I think she would be a strong candidate."
Anderson said Winfrey would need to travel to small-town America and "start having some real conversations with real people" about a presidential run.
"I do think Oprah would certainly appeal to suburbanites who, for whatever reason, think Democrats are not great on business or job creation, because she has a pretty strong and successful business background," he said. "I think where we win on 2020 is connecting with middle class voters in rural parts of the country who feel like they've been ignored by both parties for years."
Sanders world is skeptical
Supporters of Sanders warn against nominating someone without deep policy experience to take on Trump.
"We don't need an apprentice at this point in time. We got one. What you see when you have someone is that they can be whipsawed so easily," said RoseAnn DeMoro, the executive director of National Nurses United, a major Sanders backer in 2016.
"Everyone loves Oprah," DeMoro said. "The problem is that we are on the precipice of an extremely dangerous time in history, and I believe that this calls for the most seasoned, knowledgeable, in-depth president. To get us to unwind what's going to happen by 2020 is going to take enormous experience."
And Josh Fox, the director of Gasland, who has worked with the liberal group Our Revolution, tweeted his objection: "No more neoliberals please. #Bernie2020"