NEW YORK — A liberal billionaire whose face is plastered on televisions across the country took a significant step toward a potential presidential run on Monday.

And Oprah Winfrey joined the 2020 discussion, too.


Just hours after the entertainment mogul stormed into the 2020 sweepstakes with a speech that had the distinct ring of a presidential campaign warm-up, hedge fund manager-turned-activist Tom Steyer showed up in Washington to announce plans to plow $30 million into flipping the House, while amping up his push to impeach Donald Trump.

The two of them occupy an increasingly crowded space. Eyeing the historically unpopular real estate executive sitting in the Oval Office, at least eight magnates who could fund their own campaigns have entertained — or been the focus of live speculation about — 2020 bids.

The group, which ranges from Winfrey and Steyer to Starbucks executive Howard Schultz and investor Mark Cuban, has little in common other than money, antipathy toward Trump, and coyness about potential bids. Some may run as Democrats, others as Independents, and others still as Republicans.

“As I’ve said repeatedly, I am willing to do whatever it takes to save our country,” Steyer told reporters on Monday in Washington, offering a similar type of savior-from-Trump rationale for his moves that other billionaires are openly or privately entertaining, even as he denied that his latest announcement was about 2020.

As the midterm election nears, some of the business barons have begun looking at the possibility more seriously, according to a wide range of potential pols, advisers and friends who detailed their considerations to POLITICO.





POLITICO Playbook newsletter Sign up today to receive the #1-rated newsletter in politics Email Sign Up By signing up you agree to receive email newsletters or alerts from POLITICO. You can unsubscribe at any time. This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

While they would not need to spend time raising money, some acknowledge they could use the year to build political goodwill and name recognition. Others are looking at what it would take to run a campaign outside of the traditional two-party system, wary of the massive structural obstacles to gaining viability without backing from a national party and huge celebrity, but also conscious of populist anger with the 1 percent they all represent.

One stumbling block: Other than Winfrey and perhaps businessman and Cuban, none of the potential candidates possesses the universal name ID and force of personality that helped Trump get elected as a political novice.

Still, it’s nothing new for billionaires with no political experience aside from donations to be egged toward runs by consultants eager for a paycheck, or for titans of industry to be surrounded by political professionals helping them in business as well as others telling them they’d make a great president. But the current crop sees an extra opportunity in 2020: Some of them believe the allure of a blockbuster — yet competent — executive rival to Trump would be hard to resist.

Winfrey has mostly laughed off presidential speculation in the past, and she told Bloomberg News she had no intention of running after her speech on Sunday night at the Golden Globes ceremony. But her partner, Stedman Graham, fanned the flames by leaving the door open.

“It’s up to the people,” he told a Los Angeles Times reporter at the ceremony. “She would absolutely do it.”

Winfrey-centric chatter had actually already been on a low boil for months, a frequent topic of idle conversation among Democratic operatives looking over the 52 percent national approval rating she had in a March Quinnipiac poll and the 7-point head-to-head lead she had over Trump in a Public Policy Polling survey that month.

Yet it’s Steyer — by far Democrats’ largest donor in recent election cycles, to the tune of nearly $200 million — who has moved most aggressively toward a possible campaign.

Passing on long-rumored bids for the Senate or the governor’s seat in California, Steyer’s move was the most serious step forward yet of any of the handful of billionaires considering a run for Trump’s office. Even as he insisted he hasn’t yet thought about 2020, Steyer pointedly wouldn’t rule it out.

Steyer’s political organization, NextGen, has significant footprints in early-voting and swing states across the country, and his national impeachment ad campaign has both significantly increased his name recognition among voters and gained him a 4 million-strong list of activist email addresses — a valuable political commodity. He has started going through some more traditional steps of potential presidential wannabes: He has started polling Democratic primary and caucus goers in Iowa and New Hampshire, according to polling memos viewed by Politico.

Steyer has in recent years surrounded himself with campaign veterans like Bill Clinton White House alum Chris Lehane, former Jerry Brown aide Gil Duran, former Bernie Sanders lawyer Brad Deutsch, and Obama and Hillary Clinton pollster John Anzalone, among others.

“We don’t see this as a horse race, we don’t see this as the normal push-and-pull of American politics. If we did, we would not be running a ‘Need to Impeach’ campaign,” Steyer told Politico in an interview after his Washington announcement on Monday. He called Trump and his administration “shockingly short-sighted and stupid” and “dangerous to the American people.”

As for a potential 2020 presidential campaign, Steyer said, “Anybody who’s spending time thinking past Nov. 6, 2018, is doing themselves a disservice. You have no idea where we’re going to be on Nov. 7, and neither do I.”

Cuban, who appeared occasionally with Hillary Clinton on the campaign trail in 2016 to needle Trump, confirmed to Politico he’s still considering a run after floating a balloon last year. But he said he is “not ready to commit to it. A lot can change between now and then.”

The investor famous for his ownership of the NBA’s Dallas Mavericks and his role on ABC’s “Shark Tank” said he did not yet know whether he would run with a party or as an independent, and that while has no current plans to do any political travel this year, he has in fact been in touch with a handful of political strategists and pollsters about the prospect of pursuing the presidency.

“They seem to be coming out of the woodwork,” he said. “So I’ve had quite a few conversations.”

Michael Bloomberg — who commissioned extensive polling, hired a preliminary campaign staff, produced ads and recruited a running mate in 2016 before opting against a run — has been quiet about a possible 2020 run, either as an independent or with a party. But the former New York City mayor, executive and political group financier has stepped up his climate activism and saw his Bloomberg Global Business Forum replace the Clinton Global Initiative conference in September.

While Disney executive Bob Iger was widely thought to be considering a bid until late last year, his name has since fallen out of circulation with the news that his company would acquire 21st Century Fox, a massive merger that will keep him occupied. And while even more presidential speculation has surrounded the CEO and the COO of Facebook, neither Mark Zuckerberg nor Sheryl Sandberg has made any concrete political move recently as the Internet giant has come under increased scrutiny in Washington and the founder publicly pursues his 2018 goal of “focus[ing] on fixing” his company.

The chatter around the pair isn’t entirely idle, though people close to them brush off speculation about their political ambitions, and one operative who helped organize Zuckerberg’s visit of early-voting Iowa earlier this year has even offered his services to other potential candidates, further indicating the unlikelihood of a Zuckerberg run. Sandberg, the author of “Lean In” and a former Treasury Department official, was in contact with Clinton’s campaign team in 2016, while Zuckerberg has surrounded himself with campaign veterans including Barack Obama’s 2008 campaign manager David Plouffe, George W. Bush’s 2004 campaign manager Ken Mehlman, and Obama and Hillary Clinton pollster Joel Benenson, among others.

But the corporate titan even more likely to consider a bid lives further up the West Coast, in Seattle.

Starbucks’ Schultz rarely engages with current local or national Democratic leaders, but he has maintained an ongoing dialogue with a handful of longtime campaign pros from both sides of the aisle after speaking out against what he views as Washington’s overly partisan atmosphere, say multiple operatives who have spoken with him. Schultz, whose spokesman did not respond to a request for comment, says both publicly and privately that the country is suffering from a lack of national leadership, according to acquaintances.

To multiple political professionals who’ve spoken with Schultz, his wiggle-room denials of interest in running for public office down the road — “I have no plans to run for office, I am very consistent on that,” he told Reuters in October — are further evidence that he still might consider a run.

Like Bloomberg in 2016, Schultz would likely consider running as an independent, a daunting undertaking given the lack of built-in political base that a traditional party provides.

But business leaders who have gamed out a run with operatives from both parties believe there could be room for a middle-of-the-road candidate in a contest pitting Trump against a left-wing Democrat like Bernie Sanders — a calculation that echoes Bloomberg’s in 2016.

To many pollsters and campaign strategists, however, such speculation remains the stuff of fantasy. That’s largely because of the enormous hurdles to assembling a viable candidacy and in part because of the relative lack of national name recognition plaguing nearly all the potential billionaire candidates, no matter how famous their corporations.

The best-case scenario is a Ross Perot-like candidacy that would lower the Democrats’ threshold for victory to less than 50 percent. Perot won almost 19 percent of the national vote running as an independent obsessed with the deficit, but carried no states against Bill Clinton and George H.W. Bush.

“This is really a pipe dream,” said GOP pollster Robert Blizzard. “You’ve always seen a little bit of this in statewide races, that people think just because they were successful in business they can do it in politics. But Trump is the exception, not the rule.”

Even within the traditional party structures, the path to success for such figures is treacherous in a climate where leaders on both sides regularly rail against inequality and frequently criticize the excesses and practices of the wealthy.

So even as possible contenders like Steyer shy from traditional moves like visiting New Hampshire, calling swing-state machers or making nice with party committee leaders, they are eager to be seen more as activists than simply high-flying donors.

It may be a political necessity.

“It’s a symptom of the cancer of the big money in politics: People think just because they have a lot of money, they think they can run for office,” said Larry Cohen, a former head of the Communications Workers of America who now chairs the board of Our Revolution, the political group built out of Sanders’ 2016 presidential campaign.

“It’s one thing to say we need new people,” he added. “But this isn’t what we mean.”

