There is probably never a bad time to be a billionaire. But this, at least, is an especially complicated one.
Yes, one billionaire is president — if President Trump’s financial self-assessments are to be believed, in lieu of his tax returns — and at least one more, Tom Steyer, is running to succeed him.
Yet as a more famous and formidable avatar of the mega-rich, former New York City mayor Michael R. Bloomberg, moves toward a run of his own in a 2020 Democratic primary defined largely by economic inequality, he is stepping into a public moment uniquely fraught for the three-comma set.
Across politics, technology and popular culture, the wisdom and purpose of the extremely wealthy is being questioned as never before. Billionaires, led by Bill Gates and the hedge fund manager Leon Cooperman, have quarreled this week with one of the top Democratic contenders, Senator Elizabeth Warren, over the way she talks about affluence.
Mark Zuckerberg, no longer lionized as the Facebook wunderkind in an unpretentious hoodie, has been hauled before Congress for televised floggings over privacy and advertising standards. Adam Neumann of WeWork has been scorned as an archetype of start-up chicanery, walking away with a $185 million “consulting fee” and potentially far more in sold-off shares after effectively running the company into the ground. HBO has built a hit show, “Succession,” around the dim morality of an ultrawealthy media family.
So convoluted are the billionaire wars that on Friday, the Democratic primary descended into multibillionaire sniping: Mr. Steyer, seeking to distinguish himself from his would-be rival, called on Mr. Bloomberg to either support a wealth tax or sit out the primary.
“I missed that,” said Howard Wolfson, a top adviser to Mr. Bloomberg, when told of Mr. Steyer’s challenge. “Is he still running?”
Mr. Bloomberg’s allies plainly see him as a more credible contender — not just a business giant but a former three-term mayor of the country’s largest city, with a national reputation buoyed by high-dollar philanthropy and activism on gun control and environmental issues.
“He’s run for office three times as a billionaire and won three times,” Mr. Wolfson said, adding that voters valued that he was self-made. “It’s not the first time he’s been attacked for being a billionaire.”
Still, in the years since Mr. Bloomberg left office, polls have shown a wide-scale distrust of billionaires, once celebrated as the pinnacle of American achievement. Many Democratic candidates have done the math — 99.999999 percent is larger than .000001 percent — and campaigned accordingly.
Senator Bernie Sanders has said he does not believe billionaires should exist at all. Ms. Warren has delighted in taunting them with a customized tax-bill calculator on her website, infusing her stump speech with a faux-sympathetic “awwwwww” after telling voters about the very-upper-class opposition to her wealth tax proposal.
At an event in Greensboro, N.C., on Thursday, which found Ms. Warren onstage for a word association game with an interviewer, one of the prompts was “billionaires.”
“Boohoo,” she said, breaking into mock tears.
Such is the unsubtlety of the nation’s present debate: a real-time collision of topple-the-plutocracy candidates and actual plutocrats in the same presidential field, injecting the race with a raft of questions that suddenly seem less academic:
In a primary consumed by talk of corporate excesses, with top candidates mostly in their 70s, can Mr. Bloomberg, a 77-year-old titan of high finance, really find a major audience?
Might his entry only boost the progressive candidates whose ascent — coupled with the stumbles of former Vice President Joseph R. Biden Jr. — so troubled Mr. Bloomberg in the first place, supplying them with another flesh-and-blood billionaire against whom they can make their case?
And, at a more fundamental level, what does America expect of its billionaires in 2019? How are they supposed to behave when the first line on their résumés, the one they worked so hard to acquire, is liable to attract suspicion from a not-insignificant segment of the population?
“To whom much is given, much is required,” said Randi Weingarten, the president of the American Federation of Teachers, who clashed often with Mr. Bloomberg’s education team when he was mayor. “There is great income and wealth inequality in this country, greater than any other time since the Gilded Age. If a billionaire is going to run, a billionaire has to understand that.”
Against this backdrop of simmering populist anger, growing since the Occupy movement of 2011 into a mainstream political force, several billionaires have stepped forward to defend their kind, particularly in reaction to Ms. Warren’s policy plans, which stand to cost them considerably.
Last month, Mr. Cooperman, the billionaire money manager, published a letter criticizing Ms. Warren’s “vilification of the rich.” He told CNBC on Friday that Mr. Bloomberg has his support if he runs.
Mr. Gates, speaking at The New York Times DealBook Conference this week, lamented the “incentive system” at play in Ms. Warren’s tax proposals, wondering aloud if Ms. Warren would even “be willing to sit down with somebody, you know, who has large amounts of money.” (Ms. Warren responded with a tweet offering to explain her ideas in person.)
Earlier this year, Mr. Gates noted what he saw as an oddity of the modern age. “It is fascinating,” he told Forbes, “that for the first time in my life, people are saying, ‘O.K., should you have billionaires?’” Mr. Gates concluded that, yes, you should. But he allowed that a more “neutral witness,” someone without a billion dollars, might be a better messenger.
Recent campaign history for billionaires is mixed, even for candidates investing tens of millions of dollars of their own money, often at minimum. There have been triumphs, including Mr. Bloomberg’s three victories in New York and the election last year of J.B. Pritzker, the billionaire heir to the Hyatt hotel fortune who is now governor of Illinois.
In 1992, Ross Perot, a twanging Texan who drew from his billions to become a factor in the presidential race between Bill Clinton and George H.W. Bush, took 19 percent of the popular vote as an independent. Steve Forbes ran twice in Republican presidential primaries, 1996 and 2000, to little electoral effect.
On this score, Mr. Trump is the most unalloyed success, fusing boardroom bravado and constant exaggeration to convince his supporters that his vast wealth was an asset. He even boasted of past donations to politicians as evidence that only an insider mogul — someone who knew the game was rigged because he had been rigging it — could be trusted to right such wrongs.
Mr. Wolfson suggested that Mr. Bloomberg could offer his own take on an above-it-all pitch. “That was a powerful part of his appeal when he was mayor: He cannot be bought,” Mr. Wolfson said, noting that Mr. Bloomberg favors raising taxes on “upper-income earners.” “He is unbought and unbossed.”
But thus far this cycle, candidates have struggled at times to connect their financial conquests to voters’ experiences, supplying limited evidence that non-Trump entrepreneurs can find serious traction.
Mr. Steyer, a hedge fund billionaire turned impeachment activist, has qualified for two Democratic debates but left little mark on the race to date, save for his ubiquitous advertising footprint and an Associated Press report that a top aide privately offered campaign contributions to local candidates willing to endorse Mr. Steyer. (The campaign apologized for “any miscommunication” it might have conveyed to these candidates. The aide offered his resignation on Friday.)
Howard Schultz, the former chief executive of Starbucks, weighed an independent run this year before backing away. His flirtation was greeted most vocally by pleas from Mr. Trump’s opponents, who viewed Mr. Schultz as an out-of-touch spoiler whose prospective bid would only help the president.
“The obvious challenge is that everyone overlooks the drivers that turned these guys into billionaires,” said Erin McPike, a former Schultz aide, “and those are key qualifications.”
It has been a decade since Mr. Bloomberg last appeared on a ballot, inviting concerns that he may show significant rust as a candidate. Rarely folksy as mayor, he was prone to tin-eared flourishes, caricatured in the news media for spending weekends in Bermuda or urging snowed-in residents to take in a Broadway show during a blizzard.
Some voters seem inclined to forgive any sins of tone, if the platform is right. “Just because a guy’s a billionaire doesn’t make you a bad person,” said Patrick Mirocha, 46, from Davenport, Iowa, a self-described liberal waiting to see Ms. Warren speak last weekend.
In an address this spring to Harvard Business School’s graduating class, Mr. Bloomberg perhaps hinted at the kind of message he might fashion to describe his own career. “People have a hell of a lot more respect for those who make a difference in society than they do for people who just make money,” he said, adding, “Gordon Gekko was wrong: Greed ain’t good.”
On the question of greed, and whether too much power is concentrated in the hands of too few, the public seems to agree. A 2017 survey considered attitudes toward the ultrarich. It found that 53 percent of Americans distrusted billionaires, while 31 percent said they admired them.
The organization behind that poll: Bloomberg News.
Thomas Kaplan contributed reporting.