Michael Bloomberg is a kind of shadow 2020 presidential candidate. He hasn’t turned up on a debate stage. He won’t be on a ballot for weeks. But if you watch TV or open up Facebook, you can’t avoid him. There are Bloomberg ads everywhere. His campaign is spending millions every week. He’s retaining prominence despite skipping the early states. And it all might be paying off.

On Wednesday’s episode of What Next, I spoke with Edward-Isaac Dovere, an Atlantic staff writer who has covered Bloomberg’s political career for more than a decade. In our conversation, which has been edited and condensed for clarity, we discussed Bloomberg’s plan for victory and what nominating him would mean for the Democratic Party, and for the rest of us.

Mary Harris: Bloomberg has thought about running for president before. I’m wondering what makes this time different.

Edward-Isaac Dovere: I wrote my first “Bloomberg for President?” article in 2007. Bloomberg thought about it when he won his second term in 2005 as mayor. And then he left the Republican Party in 2007 and registered as an independent. That was part of a plan to run in 2008. He had staff that started to go around the country and explore ballot access questions and put together the pieces of what would have been a run then. Obviously it never happened, but it got reasonably far down the line. There was some talk about running maybe in 2012, but nothing more than a couple of conversations.

But in 2016, he actually had scripted ads.

In 2016 there was a full-on plan that got built. He was watching what was going on in the Republican Party, when Donald Trump was just crushing all of the expected Republican shining lights. And on the Democratic side, the weakness of Hillary Clinton was a real consideration even before Bernie Sanders exposed that weakness. And Bloomberg got really deep into thinking about it.

But his scheme to get elected back in 2016 was unorthodox. He wanted to get enough votes as an independent to trigger the involvement of Congress.

The plan was for him to run as an independent and hope that they could win enough states to throw the election to the House of Representatives. As the Constitution lays out, if nobody gets 270 electoral votes or a majority of electoral votes, it goes to the House of Representatives. Then the House votes, with each delegation from each state getting one vote.

The strategy now in 2020 is to skip the early states, which have traditionally been the places you go to sort of win over the field and burnish your reputation. Bloomberg really wants to make a big splash on Super Tuesday, and then it sounds like he wants to kind of go in and work all the advantages to get all the delegates he needs. It doesn’t sound particularly democratic.

Well, what also might not sound particularly democratic to people is that Iowa and New Hampshire, for some reason, get this primacy in deciding who the Democratic or Republican nominee is going to be. Iowa and New Hampshire are not representative of the country in any real way, demographically, geographically. There are no big cities in either of them, with apologies to both Des Moines and Manchester. What Bloomberg is saying is, Why do we do it this way? This is a silly way of doing it.

Do you think it can work?

Maybe. I think that we are seeing in real time, as someone who spent his Monday night at a Holiday Inn in West Des Moines watching a caucus go down and then the caucus come apart, we are watching all of the things that we assumed about politics over the last couple of years come apart. Trump is the president of the United States, right? He has been impeached and acquitted. We’ve never had a president who has been impeached run for reelection before, because Andrew Johnson and Bill Clinton were both finished as president a couple of years later.

“Imagine that you can pay for your opposition to just be quiet. Then suddenly you don’t seem like you’re unpopular, even in places where you might be.”

Over 12 years as mayor of New York City, Bloomberg took on problems other mayors had struggled with. He treated municipal systems like a business and used data to reshape how City Hall worked. He also leveraged his personal wealth to make complicated decisions simpler. He would slash funding in the city’s budget, but then he could backfill those cuts with anonymous donations. He would give to political organizations. He spent money on advertising.

If you look at what happened with the smoking ban—which was one of the first things that Bloomberg did when he was mayor—there was huge resistance to that among people who just didn’t really want to change the way things were. They were spending a lot of money, and Bloomberg looked at it and he spent more and drowned them out. Now, the smoking ban is just a part of New York.

I think this shows this other really important tenet of how Bloomberg presides: When you can’t find a way, find someone to pay to get your way.

Bloomberg often gets a lot of attention for how much money he spent on campaigns. He spent more than that when he was mayor, between the races: funding, writing checks, inviting people to come play golf and stay at his home in Bermuda, flying on his private plane, advertising campaigns, the smoking ban, some of the education changes that he got. He was using the money as a way of bulldozing the opposition, of giving a support structure that people needed and wanted to be there in order to get what he wanted through, and make it so that he had an agenda that was able to progress. He also used it to drown out the opposition. That is something that’s very, very special for a mayor to be able to pull off, and only he has been able to do that. Imagine that you can pay for your opposition to just be quiet. Then suddenly you don’t seem like you’re unpopular, even in places where you might be.

I wonder, at the national level, whether it’s possible to govern in this way, just because the numbers are so different. They are so much bigger.

And I don’t think that we should expect that if he were president, he would do it in quite the same way and spend $1 billion a year backing himself up. Let’s say President Bloomberg wanted to get an infrastructure bill passed, and he was running up against resistance to it. Would he start funding advertising in certain congressional districts? I feel like yes, probably.

This tactic of using money to silence critics—Bloomberg has done it for a long time in a lot of different contexts. For years, he faced allegations that women in his orbit had been mistreated. One employee said he encouraged her to kill her baby after announcing she was pregnant. Others said he’d sexualized his female workforce. In this first presidential election since the #MeToo movement went viral, it’s an open question how Bloomberg will be asked to reckon with all this.

We’ve seen the beginning of it, which is that there are people who say that they have nondisclosure agreements that they would like to be released from, and Bloomberg has said no. And so that means that there is less that can be known or said about what happened. Although some of this has come out because of some lawsuits that have a long history that, not just this year that this stuff started coming out.

His candidacy is really propelled by and has so much to do with his money. It’s why he can be here and make this argument that having all this money makes him less corruptible, and it’s really appealing—he doesn’t have to care what people think of him. But I think that if he continues to have this momentum, the conversation we’re going to be having as part of this Democratic primary is whether being rich makes you corruptible, and whether Americans care about that.

Bloomberg is about the money here. There’s no question about it. The money is an enormous part of that. And it’s a really odd fit for the Democratic Party at this point. I think his campaign would not even be within the realm of possibility if there weren’t such a level of anxiety among Democrats about beating Trump. It keeps coming back to the money for a lot of people, and that makes many other Democrats very uncomfortable. I was at an event in Iowa City a couple of days before the caucuses with Elizabeth Warren, and she called Bloomberg a danger to our democracy with the way that he is running the campaign, spending this much and skipping the early states. Not him, but the campaign was a danger to our democracy. That’s the way she said it.

Do you think Bloomberg would be a viable candidate without Trump to run against?

If you remove Bloomberg’s money from the equation, if you remove Trump as the opposition, I’m not sure that we’re having this conversation at all, but that’s the world that we live in.

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