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On Sunday, former New York City Mayor Michael Bloomberg made it official: After a series of past head fakes, he’s running for the Democratic presidential nomination in 2020.

Bloomberg quickly put his money where his mouth is, laying out $37 million out of his own fortune to fund a massive two-week ad campaign in states that will vote on Super Tuesday (March 3) or later. And Bloomberg was on the trail in Virginia (primary date March 3) already on Monday.

So what do we make of Bloomberg (and his billions)? Is this a pure vanity campaign? Or does Bloomberg actually have a path? I put those questions to Azi Paybarah, a New York Times metro reporter who has been following Bloomberg’s career for more than a decade.

Our conversation, lightly edited for flow, is below.

Cillizza: Michael Bloomberg is finally running for president. Did you always expect it? Or assume he would look and never do it?

Paybarah: Presidential races can have a Groundhog’s Day feel to it. Will the incumbent ditch their running mate for a fresh face? Will Democrats pick a moderate from the South or Midwest to balance their ticket? Will Bloomberg actually jump in this time?

But so much conventional wisdom was thrown out the window since 2016, it’s hard to say what’s expected anymore. What’s been true for a long time is that it’s hard to discount 1) a mayor from the largest city in the country 2) who has a giant fortune and 3) a willingness to actually use it.

Bloomberg’s interest in higher office has been present for quite a while (remember that push for a third term?). What hasn’t always been there is a plausible-ish path for him to get there.

Cillizza: Compare Bloomberg’s first run for mayor in 2001 with this run for president. Similarities? Differences?

Paybarah: Similarities: He is a party-hopping billionaire running a long-shot campaign for the nomination of a party he hasn’t always identified with.

But 2001 is not like 2020.

The coverage: Social media and marketing are playing a bigger role than earned media did when Bloomberg first dipped his toes in electoral politics. But the campaign video he released has a traditional pitch – introductory biography (he made his own fortune) – policy checkboxes (climate change, tax the rich, expanded health care coverage) – and images of lots of different kinds of people, telegraphing the idea that Bloomberg can attract votes across the board.

Oh, and the video has a few direct shots at the incumbent, rather than his Democratic primary opponents.

The candidate: Similar to 2001, he is running not to be the best representative of any party, but rather, as the most electable version of anyone who can come out of a party system.

Bloomberg’s team seems intent on running a general election strategy in the primary, with a healthy dose of outsider-isms.

Flashback: When Bloomberg prepared to run for mayor, he spent time laying the groundwork. He studied municipal government (ask Jonathan Capehart about quizzing him on the education budget) and networked with elites at his townhouse on the Upper East Side.

But he was new to the idea of retail campaigning and dealing with campaign reporters. When he did get in front of reporters, he was a bit too candid, which aides said would try to spin as the kind of refreshing candor that proved Bloomberg had the kind of authenticity and candor voters craved.

That worked to some degree, but it only took him so far. He won the Republican nomination in 2001, in part, because the party establishment (State Senator Roy Goodman, Assemblyman John Ravitz and others) was in sync with him as far as being fiscally conservative and socially liberal.

Democrats had a brutal primary and runoff and never coalesced afterward. Then, the terrorist attacks of September 11 – and the general election about a month later – cast the race in a new light. Bloomberg had argued his party infidelity was really a sign of pragmatism. His wealth was proof he could rebuild New York’s finances, and a sign of his independence from politics, everyone was in a spirit of uniting.

Cillizza: Have Bloomberg’s politics changed from when he first got into it and now? How?

Paybarah: The details have changed, but the core principle seems mostly intact.

Bloomberg believes in the free market, and the rising tide of economic prosperity to help those who are struggling. He has a lengthy record to point to when it comes to gun control, public health (smoking, calorie counts, trans fats, giant soda) immigration and same-sex marriage.

His apology for stop-and-frisk was particularly newsworthy, since he had supported the New York Police Department’s use of it for so long. But it still appears that he is firmly holding onto the broader idea that it is police intervention which plays a critical role in driving down crime, rather than improved housing for those who are struggling, and sustainable access public to mental health and other services, etc.

Ditto for his line in the campaign video about taxing the rich. In New York, he resisted such efforts, because, essentially, he said it was a bad idea to tax people who can move away. That may hold some resonance on a local level, but his video signaled he may be talking about the issue differently on the campaign trail. The details of how and why will probably get fleshed out in the days and weeks ahead.

Cillizza: Bloomberg has always faced charges he is trying to buy elections. How has he handled it in the past?

Paybarah: Bloomberg’s team has acknowledged their willingness to heavily outspend any opponent.

At first, it was described as a necessity because nobody knew him and he was running as a candidate either from a minor party (sorry, New York City Republicans) or as an incumbent essentially without a party.

His campaign says spending his own money buys them an opportunity to be heard without being sullied by special interests. That argument taps into voters’ natural suspicions about every candidate who has to shake the tin cup either online or in the Hamptons.

There’s also a tactical advantage to this big talk about big money. It could make someone rethink whether they want to be on the receiving end of all that spending. (Anthony Weiner used this as his reasoning for getting out the mayor’s race in 2009, though, it’s unclear he would have gotten the Democratic nomination that year anyway.)

What is less clear is how his indirect spending filters into politics His philanthropic giving is so vast it can be hard to trace where it goes and where it doesn’t. Somebody page Jane Mayer!

Cillizza: Finish this sentence: “Michael Bloomberg wins ________ primaries/caucuses in his run for president in 2020.” Now, explain why.

Paybarah: Thanks for trying to get me in trouble, Chris!

Michael Bloomberg wins at least as many, or more primaries and caucuses than his immediate predecessor and successor. Get it?

He’s relying on a general election message to work in big-state strategy, with a few front-runners stumbling along the way. That’s some double or triple bank shot and anyone who’s played billiards with me knows I’m no good at seeing, let alone, hitting those.

If Bloomberg has success with voters, it going to be, in part, based on how voters think of New York City – post-Giuliani, pre-de Blasio. And who doesn’t have an opinion about this city? But primary voters also are clearly looking at who can win in November. And that’s has a lot to do with another guy from New York.