Mike Bloomberg holding a microphone
Mike Bloomberg's team insists that he'd be the Democrat with the best chance of winning swing voters in swing states. (Simon Dawson / Reuters)

Michael Bloomberg Can Buy Popularity, but Can He Buy the Presidency?

If the stop-and-frisk mayor runs in 2020, he’ll have to convince voters that he’s done more good than harm in elected office—and that he’s actually a Democrat.

Here’s the premise: A white, by then 78-year-old New Yorker, who built his fortune on Wall Street and is one of its most vocal defenders, and who’s had issues with African Americans and women, is the answer to what’s going on in the Democratic Party right now.

Oh, and he’s a former Republican. And he’s a terrible campaigner whose signature move is awkwardly asking kids to give him high fives. And he says he’s not sure how true all the accusations against Charlie Rose are. But … he does have close to $50 billion. And he did spend Saturday night in New Hampshire.

So Mike Bloomberg can maybe run for president as a Democrat?

Or, as so many politicos and reporters have been reacting to the talk: Are we really doing this again?

His team thinks he could win over voters who don’t like him, because they are desperate to win—his appeal is right in line with the people in the states the party needs. Donald Trump couldn’t mock him for being too far to the left, and even if the president is somehow worth what he claims to be, Bloomberg is worth at least 15 times as much.

They think he has until around next summer to decide.

We’re at the stage of the Bloomberg-for-president bubble inflation when pretty much no one believes he’ll actually go through with it, but his small circle of media-fascination-stoking virtuosos are excelling at what he pays them hundreds of thousands of dollars a year to do.

Bloomberg himself sees a campaign as still far-fetched, according to people who have spoken to him about it, though he misses the spotlight and can’t help wondering if it could work. The life of full-time philanthropy he said he was going to devote himself to when he finished as mayor of New York never really interested him. The company he returned to running when he gave up on that doesn’t really need him. He’s bored. He thinks Trump’s a moron.

“Mike Bloomberg would like to be president, and he looks at a situation that he thinks he can help,” says Kevin Sheekey, who ran Bloomberg’s 2001 mayoral campaign and who has been coyly floating presidential speculation every few years since he first did so in an interview on NY1 the night after Bloomberg was reelected in 2005—and who urged that this quote be on the record. “Whether or not he wants to run for president is a question.”

He is definitely enjoying being in demand again, and having crowds crush around to see him, showing up in his black-tasseled loafers at the annual seafood gala for the Camden, New Jersey, Democrats he headlined in late September. He likes being thought of, at least by some in the punditry and political intelligentsia, as the savior from Donald Trump, who might just be able to win the White House on his own terms. He likes those articles about himself in The New York Times and being mentioned on the Sunday-morning talk shows, which he is old and insistent enough to still think of as the only outlets that matter in the media. He does not know the password to the Instagram account his aides used to announce that he’d reregistered as a Democrat on Wednesday morning.

Asked on Saturday night during that New Hampshire trip how he’d deal with the party’s surging progressive energy, Bloomberg repeated an argument that his aides have been nudging around for months: “There are an awful lot of other people who say if you talk to Democrats, they’re much more centrist than people understand.’’

The response from Democratic operatives and officials around the country is laughter. And when they’re not laughing, they’re just confused. One compared imagining the way Bloomberg would be greeted in a primary field to the opening scene of Saving Private Ryan.

But, as has happened throughout Bloomberg’s political career, his money—already topping $100 million this cycle, making him by far the biggest Democratic donor in 2018 (though still under the $109 million he spent in just the five boroughs on his own campaign for a third term)—has bought a lot of silence.

“I don’t want to say anything negative about him, because I want him to come and spend a lot of fucking money here for the next four weeks,” said one top Democrat in a key state.

“I give him a lot of credit for what he’s done on guns. He’s personally put a lot of money into it (and has been doing so for a while now). So I’m not going to slam the guy publicly, even if my honest assessment is that he has little chance of winning,” texted a Democratic congressman, who added, “Seeing him campaigning in Iowa will be funny and fascinating.”

Some are more diplomatic, like John Fetterman, the Braddock, Pennsylvania, mayor and lieutenant-governor nominee who’s seen by many as embodying an important new strain of left-behind progressivism for the Democratic Party’s future. He praised Bloomberg for “compassionate pragmatism” and management skills, while noting, “In a Democratic primary, you’re going to have a much different perspective. I think he has a series of barriers and challenges given where the party is going overall.”

Some are more dismissive, like Representative Ro Khanna.

“Donald Trump ruined it for billionaires,” the Silicon Valley congressman, who’s identified himself with the Bernie Sanders wing of the party, told me in June, when the Bloomberg rumors were first being floated—right around the time of Alexandria Ocasio-Cortez’s surprise primary win in a district that includes parts of Queens, which helped carry Bloomberg in his three elections.

The PAC that’s supporting Andrew Gillum, the Democratic nominee for governor in Florida, got a $250,000 check, and Bloomberg then appeared with Gillum at a center for Jewish seniors in Florida last week. *

Bloomberg’s 2020 math is also almost all about money.

For a guy who has nearly $50 billion and earns a couple billion more in interest every year, people who have been having the conversations point out, there’s no difference between spending $500 million and $3 billion. Or more. The unacknowledged reality of the supposedly enormous presidential-primary field is that it’s likely to be a long slog, and that will require at least $40 million to keep a campaign running into the spring. Add that superexpensive California is for the first time going to be right after the South Carolina primary, headlining a day of at least nine states voting on the first Tuesday in March 2020, and it matters that Bloomberg could be easily writing checks to buy wall-to-wall TV time in the Los Angeles market while his opponents are running between cocktail receptions where they’ll be lucky to pull in a few hundred thousand bucks.

They’d lean in to the work he’s done promoting gun control, years of support for Planned Parenthood, becoming a global leader on climate change, and speaking up for immigration.

“There’s lots of reasons to talk about Mike Bloomberg in a vacuum and say he doesn’t fit in a Democratic primary. But you don’t look at it in a vacuum,” Sheekey said. “The question isn’t who is he, but it’s ‘How does Mike stack up against 11 other candidates—and what has Mike done compared to the other 11?’”

Then there’s stop-and-frisk, the New York police program that let cops search anyone on the street they wanted, whenever they wanted. The police department argued it was just coincidence that most of the people stopped were young black men.

I asked Hazel Dukes, the president of the New York chapter of the NAACP, whether Bloomberg would be able to move past those years of what was seen as endorsed racism and harassment.

“I don’t think so,” she said.

The best that Bloomberg’s team has come up with to blunt that is to talk up all he’s done to reduce gun violence, pushing the idea that he’s helped save more black and brown lives than anyone realized. Or as Bloomberg himself put it in 2014, when talking about his record on guns, the citywide ban on smoking in restaurants and bars that quickly became a global norm, and anti-obesity campaigns: “I am telling you, if there is a God, when I get to heaven I’m not stopping to be interviewed. I am heading straight in. I have earned my place in heaven. It’s not even close.”

Al Sharpton, who had a good working relationship with Bloomberg while he was mayor, said that although stop-and-frisk “would be a problem, it wouldn’t be insurmountable.”

“He would have the same advantage he had running for mayor,” Sharpton said. “Because we were so mad at [Rudy] Giuliani, we forgot he’d never marched with us. Because we’re so mad at Trump, it’s almost like déjà vu.”

Sharpton said Bloomberg “could be a billionaire version of Bill Clinton, like the DLC done 21st century.”

He then noted that he ran against exactly that kind of politics himself in the 2004 primary.

Bloomberg joined the Republican Party as a way of getting around the 2001 Democratic mayoral primary in New York, then threw himself into courting the state GOP and bringing the 2004 Republican convention to Madison Square Garden. When he was thinking of running for president in 2008, he reregistered as an independent and quietly paid an aide to go around the country preparing the framework to get him on the ballot, according to people who were involved. He took a more cursory look at running in 2012, having privately complained that Barack Obama was inexperienced and wrong on business issues, and telling Rupert Murdoch after a round of presidential golf that Obama was the most “arrogant man” he’d ever met.

When Bloomberg was thinking of running in 2016, he had aides dispatch teams to key states, do polls, and build a plan that depended on a deadlocked election throwing the decision to the House of Representatives, where they thought he might be able to prevail. Bradley Tusk, an aide who would likely have been the 2016 campaign manager, writes in a just-published book that he even drew up a fantasy Cabinet—including Bill Gates as secretary of state, Oprah Winfrey as commerce secretary, Elon Musk as energy secretary, and Gabby Giffords in charge of the Bureau of Alcohol, Tobacco, Firearms, and Explosives.

So far, there isn’t permanent staff on the ground anywhere, say people involved. Most in the Bloomberg orbit roll their eyes at “Kevin being Kevin,” as Sheekey’s Dennis the Menace–style pot-stirring has become known. He’s been seeding the idea through old friends among reporters. Howard Wolfson has been taking the lead on doling out the campaign cash and scheduling appearances. A few others have pitched in, like the longtime right hand Patti Harris, and the former city-hall press secretaries Stu Loeser and Marc LaVorgna. But the circle has remained small.

“It’s much more ad hoc than you’d think,” said one person in the Bloomberg camp.

None of them has been involved in a campaign since the last time Bloomberg ran, in 2009, long before the earthquakes that have transformed politics since. With the exception of Wolfson, who was the communications director for Hillary Clinton’s 2008 White House run, most of them haven’t done much in politics outside New York. The only time Bloomberg’s machinery worked on anything directly political other than electing him mayor was the 2008 effort to get Caroline Kennedy appointed to Clinton’s Senate seat, which ended in a spectacular face-plant.

Then there are all the Republicans he’s helped along the way, and is continuing to now. Yes, he slammed Trump as a con man onstage at the 2016 Democratic convention in Philadelphia, but he did it while helping bankroll the reelection campaign of Senator Pat Toomey, who both co-sponsored the failed post-Newtown background-check gun bill and who took the bold stance of refusing to answer whom he was supporting for president until announcing on Election Day that he’d picked Trump.

In a Senate that just confirmed Brett Kavanaugh by two votes, that’s a decision with consequences.

Nor has Bloomberg’s new commitment to a Democratic majority in the House stopped him from backing old Republican friends, like Representative Dan Donovan, a top target for his seat in Staten Island, or Representative Pete King, lower on the Democratic prospect list, but higher on the Democratic rage list for comments over the years like calling for the mass surveillance of Muslims and saying they don’t act “American” when the country is under attack.

“He’s not going to like that I say this, but in many ways, he’s like Donald Trump,” King told me the day Bloomberg switched his registration. “Donald Trump didn’t really run as a Republican; he used the Republican Party to run. Mike’s just using the Democrats to run.”

He recalled being with Bloomberg and Trump at Ground Zero for the 9/11 memorial service in 2016, expecting to get caught in the middle of a fight, and being surprised by how cordial they were.

“They certainly seemed to be speaking the language,” King said. “Maybe it’s the language of billionaires.”

King kept calling the former mayor a good friend, laughing about a night when he was invited over to watch Driving Miss Daisy and then being joined at dinner afterward by James Earl Jones. So I asked him what he’d do in an election that pitted his friend against a president whom he’s been a big defender of.

“I’d have to go with President Trump, because he’s a Republican,” King said. “But you wouldn’t hear me saying a bad word about Mike Bloomberg.”

Then there’s Bloomberg’s history with women. His company has been sued for discrimination against pregnant women, including one who famously alleged that he greeted the news of her pregnancy by telling her to “kill it.” And he has made comments for years about women’s looks and his own interest in having sex with them.

There’s the real possibility that a Bloomberg 2020 primary run would go down much like Meg Whitman’s 2010 campaign for California governor, when she dumped $144 million into losing by 13 points to an old liberal who had already held the job for eight years 30 years before. Bloomberg’s team knows it. They know that if he runs, they’ll have to get him into the mind-set of his first mayoral campaign, which he knew he would likely lose, rather than his 2016 presidential exploration, when he refused to take a chance unless his team could tell him he’d win.

Not a lot of people are expecting that Sheekey or anyone else will get Bloomberg to pull the trigger, once he finishes having fun toying with the idea and really looks at the data. “You don’t get to be where he is,” said one person who’s talked with him about running, “by being an idiot.”

* This article originally stated that Michael Bloomberg had made a contribution to a Democrat Fred Hubbell’s gubernatorial campaign in Iowa. The campaign said there was no such contribution.