Billionaires helped Democrats win. Do they stand a chance in 2020?

Tom Steyer is a longtime Democratic donor who walked away from his hedge fund in 2012 to pursue political activism full time.

Washington (CNN)Former New York Mayor Michael Bloomberg. Starbucks ex-chief executive Howard Schultz. San Francisco hedge-fund founder Tom Steyer.

Less than a decade after Democrats successfully painted Republican presidential nominee Mitt Romney as a multimillionaire too out of touch to be president, their party could wind up playing host to a battle of the billionaires in 2020.
And after two of them, Bloomberg and Steyer, each plowed more than $100 million into this week's midterm elections to help Democrats successfully seize the House majority, some Democrats seem willing to listen to what they have to say.
"I don't think it's going to be a big negative," Jeff Link, a veteran Democratic strategist in Iowa, said of a billionaire potentially seeking the nomination. "Everything changed after 2016 because of Trump."
    Romney ran for president in the wake of the 2008 financial crash, when his wealth -- which came from his auto-executive father as well as his own work as a principal at private equity firm Bain Capital -- spawned endless commentary about the car elevator he planned to install at his California beach house.
    Those days are done. Romney was elected to the US Senate from Utah this week, but the real action was on the Democratic side, where a self-funding billionaire made history: J.B. Pritzker, an heir to the Hyatt hotel chain fortune, won the Illinois governor's race after spending more than $170 million to unseat Republican Gov. Bruce Rauner, a private equity mogul. Pritzker broke the previous self-funding record set in 2010 by tech executive Meg Whitman, a Republican who pumped $144 million into her failed gubernatorial bid in California.
    Another Democrat, wine magnate David Trone, captured a US House seat in DC's Maryland suburbs this week after plowing nearly $16 million of his own money into the race.

    Building political operations

    Since Trump's election, speculation has swirled around other billionaires who could seek to challenge him. Celebrity businessman and billionaire Dallas Mavericks owner Mark Cuban, who backed Democratic Hillary Clinton in 2016, has flirted with the idea (though he has signaled at times that he might run as an independent or a Republican.)
    Schultz's retirement in June as Starbucks' executive chairman -- and his sharp criticism of Trump -- has renewed talk of a possible presidential bid. He's also retained Steve Schmidt, architect of the late Sen. John McCain's 2008 Republican presidential bid.
    But among the billionaires weighing the presidency, Bloomberg and Steyer have the running start.
    Bloomberg, a former three-term New York mayor and media magnate, has a robust political operation aimed at electing candidates who support imposing gun-safety measures and confronting climate change.
    He was elected in New York as both a Republican and an independent, but announced last month that he had registered as a Democrat. He plowed more than $110 million into the midterms, much of it to help Democrats flip the House. His Independence USA super PAC spent $45 million on television in the final two weeks of the campaign alone.
    That gusher of money took Republicans by surprise.
    Bloomberg's money "was spent in a very strategic way" that made it hard for Republicans to close the gap, said Courtney Alexander of the Congressional Leadership Fund, aligned with House Republican leaders.
    "It was kind of like 'screw you' money that they could just throw around," she said Friday.
    Bloomberg's eleventh-hour infusion also took some of its beneficiaries by surprise.
    His political action committee, for instance, spent more than $400,000 on television ads in an under-radar race in Oklahoma's 5th Congressional District to aid Democrat Kendra Horn. By law, super PACs can't coordinate their spending decisions with the candidates they support.
    Ward Curtin, Horn's campaign manager, said Horn had no idea the ads were coming but that Bloomberg's team had done its homework and struck advertising themes that complemented Horn's messages.
    On Tuesday, Horn knocked off Republican Rep. Steve Russell in an Oklahoma City district Trump had won by double digits in 2016.
    "The $400,000 in this market was significant," Curtin told CNN this week. Bloomberg's move, he added, was "extremely savvy for a candidate who in some ways is introducing himself to Democrats."
    In a post-election statement, the centrist Bloomberg said he "was proud" to help Democrats serve as a "bulwark against a White House that has shown no respect for the rule of law," and he urged the Democrats "to work across the aisle to tackle tough issues" with congressional Republicans.

    Face of the resistance?

    Steyer, a longtime Democratic donor who walked away from his Farallon Capital Management hedge fund in 2012 to pursue political activism full time, has spent much of the last two years introducing himself to Americans.
    He's sought to make himself the face of the ultra-liberal, anti-Trump resistance by starring in television ads that call for the President's impeachment. This year alone, he's barnstormed the country to headline nearly 40 town hall meetings.
    Leading Democrats, however, are less than receptive to his impeachment message, worrying it could unleash GOP charges of Democratic obstruction ahead of 2020.
    "I don't think we should impeach a president for political reasons," House Democratic leader Nancy Pelosi said in an interview Thursday with CNN's Chris Cuomo. "But I don't think we should not impeach him because we think it's politically ... impeding for us to do so."
    But Steyer's aggressive stance could help his own political ambitions: He's drawn a whopping 6.2 million signatures to his impeachment petition, giving his growing political operation valuable information about a significant base of like-minded liberal voters.
    "I don't think there's anyone who has a bigger list in the Democratic Party right now," said Chris Lehane, a former aide to President Bill Clinton and a former Steyer adviser.
    Steyer pegs his midterm spending at $120 million. His political groups employed 750 people and drew 15,000 volunteers to what he called the largest youth turnout drive in US history.
    Steyer also has had high-profile stumbles on his path to a potential presidential bid. In the 2014 election cycle, for instance, his losses in Senate races outnumbered his wins despite investing more $70 million in contests that year.
    And he gained notoriety for early political stunts, such as renting an airplane to fly banners over Boston sporting events in 2013, accusing a Republican US Senate candidate of "Running for Big Oil."
    In a wide-ranging interview with CNN this week, Steyer said he's learned lessons since plunging into politics six years ago.
    "American politics are not as transparent as people think. Understanding it is something that takes a lot of effort," Steyer said.

    Can you relate?

    In a post-election conference call this week with journalists and about 1,600 staffers and volunteers aligned with his political organizations, Steyer also insisted that he grasps the American electorate and its worries about issues such as college affordability and health care costs after a year of relentless travel.
    "Whoever is going to be the nominee of either party, I think the critical question is: Do you understand what's going on in the ground, really, for people?" he said.
    Ian Russell, a Democratic strategist and former political director of the party's House campaign committee, said he doesn't "think there's an anti-rich-guy mood" in the party's electorate. But he said Democrats are going to be looking for who can win, in a presidential race likely awash in cash from large and small Democratic donors eager to oust Trump.
    "There will be a lot more obsession with candidate quality than money," he said, particularly among the Democratic Party activists and voters in early contests in places such as Iowa and New Hampshire.
    Link, the Iowa strategist, worked on President Barack Obama's campaign in 2008 and again in 2012, when Democrats cast Romney, the GOP nominee, as an uncaring multimillionaire. He said Obama and his allies could attack Romney because of his role at Bain, whose investments led to layoffs and outsourcing.
      But Trump's populist appeal proves that enormous riches do not automatically disqualify a candidate, Link said. "Trump, to his base, is completely in touch with them, he said.
      And at a time when Democratic Party activists worry about the growing influence of anonymous money in elections, Link said: "These candidates can say, 'I can tell you where all the money is coming from. It's coming from me.' "