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For seven months after Michael Bloomberg first passed on running for president in 2020, the former New York City mayor and his tight team of political advisers reviewed the constant flow of polling data they kept commissioning from all over the country and felt mostly okay. The tycoon was at some version of peace about his decision to stay out of the fray — just like he had in 2016 and 2008 — largely because Joe Biden looked well positioned to win the Democratic primary, and then to beat Donald Trump. Bloomberg almost definitely would’ve gotten into the race if the former vice-president wasn’t looking so strong in the spring, his friends said at the time. And for the next six months-plus, they repeated that intel to themselves, to their colleagues, and to anyone who pointed out that Biden, 2020’s moderate standard-bearer, was hardly a strong front-runner. Bloomberg himself was watching closely, of course, trusting in Biden but wondering aloud in private with increasing agitation as the year matured — just like everyone else — about whether anyone in the field was truly ready to beat Trump. But the data, for seven months, held up.

Then Bloomberg’s privately commissioned polls started telling a different story. As news of Trump’s attempted Ukraine extortion spread in September, Bloomberg’s team saw “a shift: Democrats becoming hyper-focused on the issue of electability. It was always a consideration. But becoming hyper-focused,” Howard Wolfson, a top Bloomberg adviser, told New York. “There are obviously plenty of Democrats who are very excited about voting for the most progressive candidate, but what we have seen is there is a large number of Democrats who want to vote for the candidate with the best shot of winning.” Most important, it was no longer obvious to Bloomberg’s team, looking at data showing a weakened Biden — having faced constant attacks and questions about his durability and fitness to match up against Trump — was still that candidate. To Bloomberg, a Bloomberg-shaped opening was finally emerging, just like he’d quietly been musing about for months to associates and political supporters, including a handful of current and former elected officials. “He’s been thinking about this for a long time,” said former Virginia governor Terry McAuliffe, who said he had no advance notice of Bloomberg’s decision. “The thinking is, ‘Does it look like Biden has imploded?’ And obviously it’s looked more and more that way recently,” added a New York power player close with the Bloomberg team.

Biden’s team, of course, doesn’t see it this way, and its immediate concern was that Bloomberg’s entry would freeze the former VP’s already-lagging fundraising. Within hours after the first Thursday Times report of his latest moves, some top Biden aides and allies began calling their current and prospective major donors to reassure them, and to gauge their feelings about Bloomberg’s potential candidacy, according to Democrats familiar with some such conversations. Some big fish either didn’t immediately respond to the calls or told the Biden team to give them some more time — they now had to reconsider given the news.

Bloomberg’s move to start getting his name on primary ballots isn’t a final decision on a full-scale campaign, but it is a new, public stage of an evolving conversation he has been having with supporters and allies for years, especially in the last two. One of the party’s two biggest donors over the last decade, he’s remained wired in: He privately discussed a potential run last year with Democratic honchos including Senate Minority Leader Chuck Schumer, Democrats briefed on the talks said, and he’s kept in touch with others like Rhode Island governor Gina Raimondo, who leads the Democratic Governors Association, as the presidential race has evolved. Over the spring and into the summer he made no secret to associates about his preference for a centrist candidate like Biden, and his displeasure with Bernie Sanders and the ascendant Elizabeth Warren. (Sometimes this poked into public view: “I just said to Sen. Warren on the way out, ‘Senator, congratulations, it’s a nice talk. But let me just remind you if my company hadn’t been successful, we wouldn’t be here today, so enough with this stuff,’” Bloomberg joked to the audience at a Des Moines gun-safety forum in August.)

Then, in recent weeks, members of his political team, led by strategist Kevin Sheekey, ramped up their outreach to politically powerful New Yorkers over dinners and drinks. The invitees hardly needed reminding that Bloomberg — worth $52 billion, according to Forbes — had talked about spending $1 billion on an independent run in 2016, and could easily drop that much now, too.

The would-be candidate himself is not yet 100 percent convinced that he will run. Early filing deadlines for ballot access in some states forced him to go public with his possible intentions last week. But over the last few days those around Bloomberg have been working to convince political allies and potential supporters that this is for real: “Get ready,” they keep saying. And after the news broke, Bloomberg himself — notoriously not one for glad-handing — made a round of calls that would be expected of a presidential candidate, including to Democratic National Committee chairman Tom Perez and the chairmen of the state parties in Iowa and New Hampshire, operatives aware of the calls told New York.

Still, even some of his closest ideological and business allies in New York and Washington aren’t sure just how seriously to take it yet, after almost none of them got any heads-up that Bloomberg was seriously reconsidering the race. Many have requested calls or briefings from Bloomberg or his lieutenants, hoping to understand exactly where they see room for him in the race when polling shows the electorate is not actually dissatisfied with the primary field — just 4 percent said they were undecided because of a lack of good choices in a USC/Los Angeles Times survey last week. Bloomberg would also enter the race with national support between that of Kamala Harris and Andrew Yang and with the highest unfavorability rating of any Democrat — at least before unleashing his inevitable torrent of money for ads.

“This is ridiculous,” one New York Democrat in regular, friendly contact with Team Bloomberg told me. “I love those guys,” he said. But “you will not be able to find an individual who is not on their payroll who’ll say this is a good idea.”

THE PROSPECT THAT’S making many of the skeptics from the center-left particularly nervous is Bloomberg’s entry weakening support for Biden and Pete Buttigieg, arguably the two leading moderates in the race, while also himself not winning. That could clear Warren or Sanders’s path to the nomination, while giving them reason to go extra-heavy on billionaire bashing. Already both of them have made political hay of yet another tycoon’s interest in the race, as have others like Yang, Amy Klobuchar, and Cory Booker.

But Bloomberg looks like he’s trying to find a way around that outcome, employing a new game plan altogether. The idea is to skip the first four states in the nominating process, where every other candidate has already spent months and millions of dollars, and to instead build up operations in the states that vote in March, when the field will presumably be less crowded. The plan was almost immediately compared to Rudy Giuliani’s ill-fated attempt to do something similar in 2008 by not seriously contesting any states until Florida, though in reality Giuliani did briefly try to compete in the preceding states, but failed. Bloomberg, too, spent time in Iowa and New Hampshire when he was first considering a run earlier this year. In any case, it’s too late for him to try organizing them now.

The revelation of this strategy has infuriated the traditional gatekeepers in the states that usually play the biggest roles in the process. The idea came into public view in a series of reports on Friday, thanks to Wolfson, who along with Sheekey, ad maker Bill Knapp, and pollster Doug Schoen have long made up Bloomberg’s inner circle, though the mayor has also brought on Brynne Craig, a veteran of Hillary Clinton’s 2016 campaign, and worked with top Barack Obama campaign alums Mitch Stewart and Dan Wagner. Both Iowa and New Hampshire’s Democratic Party chairs almost immediately made a point of their “disappointment” (read: fury) that a candidate would skip their contests, which are central to the nominating path but constantly under threat from reformers who want to change it. The latter’s Raymond Buckley warned, “It’s unfortunate that Michael Bloomberg doesn’t want to participate in this invaluable, important, and unique primary process and be tested in the same way that the other Democratic candidates have been and will be.” But it also sparked speculation that he’s positioning himself as a white-knight candidate who could step in if Biden collapses in the first four states. It’s a plan of attack that fits perfectly with Bloomberg’s likeliest preferred campaign tactic: blanketing states with television ads and paid organizers, rather than personally stopping through diners to greet voters day after day, and trying to lead rousing rallies. “They’re looking for a coronation,” griped a senior Democratic strategist who’s worked closely with the Bloomberg operation for years. “Is he really willing to do the retail thing? Billions in ads don’t get you where you need to be. Just look at Tom Steyer.”

The entry of a well-funded, well-known candidate swooping in just as huge states begin voting could also raise the probability of a contested convention come July, warned one longtime Bloomberg associate currently being courted by both the former mayor and the former vice-president. Others who’d voiced a similar concern about Steyer — the hedge-fund billionaire and environmental and impeachment activist and the only person to spend more on Democratic politics than Bloomberg in the last decade — worried it could draw Bloomberg’s attention from his funding of liberal operations around the country, particularly around voter data and climate and gun-control issues. He’s talked about spending half a billion dollars on that work this election cycle. (“The Democrats owe him a tremendous amount of credit,” said McAuliffe, whom Bloomberg supported in his 2013 gubernatorial run, and who at one point discussed a campaign role with Biden. “I have nothing but great things to say about him.”) Bloomberg has not indicated that he would put these projects aside, and those close to him find that unlikely. But some leading party operatives who acknowledge how reliant they are on his cash and network are still nervous about the left’s funding and organizing future if he were to focus more on the campaign.

Even some of the Democrats closest to Bloomberg aren’t sure this is anything more than a trial balloon to see how voters and the media treat him before fully committing. Or, in the words of one of his longtime backers who is now on Team Biden, “an insurance policy” that might never be tapped. For one thing, it’s far from clear that Bloomberg — a former Republican and Independent — would be able to make many Biden supporters think twice. The ex-VP’s base, after all, is not suburban moderates so much as non-college-educated white voters and African-Americans in states like South Carolina. “This could be famous last words, but this may be like Wesley Clark entering, getting single digits, then not getting anywhere,” said one powerful state Democratic Party chair who hasn’t heard from Bloomberg, repeating a popular comparison to the general who entered the 2004 race in September of 2003, then flopped. Then there are Bloomberg’s repeated flirtations with running since 2006. “Until I hear Mike say, on the record, ‘I’m in,’ I won’t believe it,” another top New York City political operator close to Bloomberg’s team told me.

Even if Bloomberg ultimately decides against a run, he’s already changed the dynamics of the race for some major candidates and moneymen. For one, his tentative entry sucked up all the oxygen in the 2020 media room for the weekend, lightening the scrutiny Warren had been receiving for her Medicare for All funding plan and allowing her to regain an offensive posture by coming out swinging against his candidacy. Meanwhile, “you’re going to have billionaires out there crying tears of joy for their savior,” said a well-connected East Coast fundraiser who’s spoken extensively with Bloomberg and his deputies in recent months. “The Bloomberg people are going to have to convince them to calm down.” A few minutes after we hung up, investor Leon Cooperman — who’s recently been attacking Warren like he did Obama in 2011 — said he’d back Bloomberg, and the next day Recode reported that Jeff Bezos had asked him to run earlier this year.

But that plutocratic brand of exuberance has its limits. Some of Bloomberg’s friends said they’re concerned that if the mayor pumps the brakes, this renewed flirtation with 2020 runs the risk of already having backfired. It hasn’t just given the populist left’s preferred candidates an easy applause line, a handful worried over the weekend, it may have cast yet another shadow over a Biden campaign that could use as much sunlight as possible these days.

“I don’t see how this doesn’t hand the nomination to Warren,” sighed a Manhattan financier, a longtime Bloomberg supporter who’d tried nudging him toward running late last year and early in 2019. This spring, after Bloomberg initially said he wouldn’t run, the financier considered a range of other candidates before settling on backing Biden. He continued, “I don’t see how this isn’t the most destructive thing he could possibly do.”