The Washington PostDemocracy Dies in Darkness

Should Democrats find a Trump of their own? Political outsiders find little room in 2020 presidential field.

Media mogul Oprah Winfrey with the Cecil B. DeMille Award during the Golden Globe Awards in January.
Media mogul Oprah Winfrey with the Cecil B. DeMille Award during the Golden Globe Awards in January. (Frederic J. Brown/AFP/Getty Images)

For a guy who says he is not running for president, Starbucks executive chairman Howard Schultz sure checked a lot of political boxes over the past week.

Upon announcing his resignation from his company, he published a snappy new website, with a direct-to-camera video and a fashionable black-and-white photo of him smiling on a Seattle street. He revealed plans to write a book, likely to be published early in 2019, about his philosophy on running a socially responsible company. And he sent an open letter to his employees announcing his desire to explore “public service.”

But it took less than 24 hours for Schultz to divulge something else — a willingness to challenge the liberal orthodoxy that courses through the Democratic Party. “We have to go after entitlements,” he said in an interview Tuesday on CNBC, after dismissing as “falsehoods” the proposals for single-payer health care and guaranteed federal jobs that have become all the rage on the left.

Starbucks CEO Howard Schultz said he believes “the country needs to become more compassionate” in an interview on Sept. 20, 2017. (Video: The Washington Post)

So it has gone for months, as Democrats poke around at the possibility of finding a non-politician candidate to challenge President Trump’s reelection campaign in 2020. In theory, there is a real opportunity for an outsider to take over the party and challenge Trump, the first American to be elected president without political or military service, on their own terms. The problem has been finding the right person to do it, particularly in a party whose voter base is more inclined to favor government experience. The potential 2020 field already includes about two dozen traditional politicians, including mayors, governors and senators.

The political outsiders who have explored candidacies include some of the biggest names in the corporate world — Disney chief Bob Iger, mega-mogul Oprah Winfrey, Facebook executive Sheryl Sandberg. But each of those people ultimately decided to give up the dream, at least for now, after feeling out Democratic strategists.

As it stands, the only remaining brand-name business leaders besides Schultz known to be actively considering a run are the liberal financier Tom Steyer, who is traveling the country to build a grass-roots effort to impeach Trump, and the celebrity entrepreneur Mark Cuban, who has taken few steps to build inroads in the Democratic Party, after saying last year he would rather run as a Republican or an independent.

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Cuban, 59, owner of professional basketball’s Dallas Mavericks and a star of the investment show “Shark Tank,” said in an email exchange that he has been focused on policy development, including a plan to reshape the nation’s health-care system, among other ideas that would “make it interesting.”

Billionaire philanthropist Oprah Winfrey may be flirting with a 2020 presidential run. (Video: Victoria Walker, Julio Negron/The Washington Post)

“Make a commitment to AI to assure that in the next 20 years, first autonomous, weaponized robots ever put to use are made in America and not in China or Russia,” he wrote.

Steyer, 60, continues to spend heavily on television advertising that casts him as a movement leader, while hosting town halls about impeachment in states including South Carolina and Colorado. He said in a recent interview that he is focused on the midterm elections. “As far as I am concerned, anybody who is thinking about 2020 is taking their eye off the ball,” he said.

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Among those who have demurred, the reasons vary. Sandberg found her trajectory complicated by the unexpected death of her husband in 2015 and, more recently, the ma­nipu­la­tion of Facebook by the Russian government in the 2016 election. Her commencement speech at MIT on Friday did not directly touch on politics, though she expressed pride in Facebook’s role in promoting movements such as the Women’s March on Washington and Black Lives Matter while lamenting that “we didn’t see all the risks coming, and we didn’t do enough to stop them.”

Iger’s ambition was hijacked by corporate happenstance. The boards of both Disney and 21st Century Fox implored him to sign a contract extension through 2021 as a condition of moving forward with the proposed combination of the two companies. People who spoke with him say he remains convinced that he had a path to win, even as he recognized the challenge that a corporate leader would have winning over the Democratic rank and file.

“He looked at it seriously enough to know that it was a viable option,” said one person with knowledge of the 67-year-old Iger’s exploration who spoke on the condition of anonymity to discuss the run. “He was also very cognizant of the fact that a Democratic primary was extremely difficult.”

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Winfrey, 64, and her friends made similar calls to Democratic strategists and leaders after she delivered a well-received speech in January at the Golden Globes, said a person familiar with the effort. Winfrey’s speech, in which she recognized victims of sexual harassment and lauded the press for “uncovering the absolute truth that keeps us from turning a blind eye to corruption and to injustice,” sparked buzz that this trailblazing African American talk-show host could be the one to take on Trump.

Winfrey, though, later revealed her conclusion in an interview with InStyle magazine: “I don’t have the DNA for it.”

One challenge for all non-politicians trying to feel out a campaign is navigating the clear differences in how Democrats and Republicans think of outsiders in politics. A test case is playing out in New York, where the actress and activist Cynthia Nixon has launched a campaign to topple Democratic Gov. Andrew M. Cuomo in the primary.

A Quinnipiac University poll in late April found a clear partisan split among voters in the state over whether they preferred to elect a governor who has experience in politics or one who is new to politics.

Republicans preferred someone new to politics by a margin of 47 percent to 38 percent. Democrats, by contrast, said they preferred experience by a margin of 75 percent to 17 percent, even though 28 percent said they supported Nixon’s campaign in the same poll.

“Democratic primary voters in general have been looking for candidates who have government experience,” said Jefrey Pollock, a Democratic pollster who counts Cuomo, a potential 2020 contender, among his clients. “They are afraid of electing people who don’t have the experience because it reminds them of the disaster that is happening in Washington.”

Nixon has tried to deal with those concerns by introducing herself to voters as a lifelong subway rider, school activist and women’s advocate, while making wonky liberal policy a centerpiece of the campaign. Only recently has she begun to mention the fictional character she played on HBO’s “Sex and the City,” penning an opinion piece about how she tries to embody Miranda’s best characteristics.

“We are actually talking about what kind of experience matters,” said Rebecca Katz, a top adviser to Nixon’s campaign. “Right now Albany is a cesspool of corruption. That is not the experience that voters want.”

Howard Schultz steps down at Starbucks — giving rise to speculation of presidential ambitions

Schultz has in many ways been preparing far longer than the other non-politician candidates for a potential run. Born in Brooklyn to an impoverished family, he built Starbucks into a $78 billion juggernaut with more than 28,000 stores in 77 countries.

As a corporate executive, he has traveled to the U.S.-Mexico border to learn about immigration concerns, studied the opioid epidemic and convened meetings around the country to discuss race relations after high-profile police shootings. When Trump announced a ban on U.S. visitors from seven predominantly Muslim countries in January 2017, Schultz announced a company goal of hiring 10,000 refugees in stores around the world.

Schultz has also styled himself as a booster of veterans’ causes and plans to attend a fundraiser for a new World War I memorial on June 18 with retired Adm. Michael Mullen, former chairman of the Joint Chiefs of Staff. His family foundation also works to create youth job opportunities.

Former senator Bill Bradley (D-N.J.), who ran for president in 2000 and until recently sat on the Starbucks board, is one of several Democrats that Schultz has spoken with about a possible campaign.

“I think Howard is an extraordinary leader. He has transformed what a corporation can do in America,” Bradley said before ticking off the benefits that Starbucks offers its employees.

Schultz’s discussions about a possible campaign date back more than a decade with both Democrats and Republicans. “The people who will post up best against Trump are people who are most opposite to Trump in the conduct of their lives,” said one strategist who knows Schultz. “In that sense, he posts up very well.”

In an email Friday to The Washington Post, Schultz said that the past week had been an emotional one and that he was not certain of his future.

“I remain profoundly concerned about the direction of the country, our standing in the world, and the millions of people being left behind,” he wrote. “As Americans we are all in this together and I’m committed to using my citizenship to be in service of others.”

Rather than criticize China, a country where Starbucks opens at least one store every day, he says, “Our problem is not China.” Instead, he blames a failure of American leadership. In 2016, at a shareholders meeting, he played clips of a speech by Robert F. Kennedy.

“The issues that we face in terms of the dysfunction and the polarization in the government is really based on a systemic problem of ideology,” he said Tuesday on CNBC. “And I think we need a very different view of how the government and how the country should be run.”

But the rules of political combat within the Democratic Party are unlikely to change without a fight, and there is a lot of public polling suggesting that the Trump era has pushed Democratic primary voters to embrace more progressive policy solutions with diminishing concern for the growing national debt.

Asked last week on CNN about Schultz’s contention that single-payer health care was an unaffordable falsehood that liberals were selling to voters, Sen. Bernie Sanders (I-Vt.), who is also making moves to prepare for another presidential campaign, did not mince words.

“I think his comment is dead wrong,” Sanders said.