Fucking Crazy...

Here's why Bloomberg insists he's not crazy

None of his assumptions is wildly implausible. It would just take all of them coming true for this to work.

By JOHN F. HARRIS, SALLY GOLDENBERG and MARC CAPUTO

Yes, say the political strategists around former New York City mayor Michael Bloomberg, the notion of him becoming the Democratic presidential nominee requires many unprecedented and highly speculative factors falling into place just so.

No, these strategists insist, the billionaire media titan and philanthropist is not crazy, and neither are they.

The evidence for the alleged non-craziness is based on polling, an emphatically low regard for the current field of Democratic candidates, and an emphatically high regard for Bloomberg’s purported assets. These include a compelling life story, a record of accomplishment as mayor, credibility with activists on gun control and climate change, and an ability to nationalize the race this coming winter and early spring with a historic torrent of money and messaging.

What Bloomberg contemplates is not so much an exercise in threading the political needle as pulverizing that needle as it has existed for decades.

“We’re just going to rewrite a new system,” said Kevin Sheekey, a senior Bloomberg strategist.

“Our theory of the case is that we’re going to skip the first four early states and we’re going to run as intensive a campaign” in other Democratic states as rivals do in Iowa and New Hampshire. That plan kicks in with the March 3 run of Super Tuesday states, but won’t stop there.

“We’re going to do it all across the country,” Sheekey said.

In background briefings, Bloomberg operatives defend this strategy in ways that makes logical sense as an abstraction but requires suspension of disbelief about numerous practical factors that are largely outside his control:

— That the contest will remain muddled and fluid until the March 3 Super Tuesday primaries (the first time Bloomberg’s name will be on the ballot), even though historically the early states have clarified the race and created frontrunners in ways that offered no path to late entrants.

— That Bloomberg’s argument that he’s best-positioned to beat President Donald Trump will be compelling eventually to African-Americans and women, even though he starts the race with gaping challenges with these groups.

— That the narrative advanced by liberal pundits, that Democrats in 2020 urgently want a more progressive agenda and a more demographically diverse nominee, is wrong — even though this is precisely what has powered Elizabeth Warren’s campaign so far.

Here is a breakdown of four key strategic assumptions of Bloomberg’s nascent campaign, along with some “yes but” analysis about why those assumptions might be wobbly. Probably there is no individual Bloomberg assumption that is wildly implausible. But it is the number of assumptions that must come together at once that make this for now a low-probability endeavor.

Assumption: Bloomberg’s rivals are losers

There’s no nice way to put it. Bloomberg operatives say he made a decision months ago not to run for president in 2020, and in recent weeks reversed course because of public and private polls that he believes shows the people currently atop the Democratic field are suffering from potentially fatal political defects.

Under the current trajectory of the race, Bloomberg’s team believes Warren is the likely nominee. By this reckoning, former Vice President Joe Biden simply has not been commanding enough in debates and other venues to inspire confidence among Democratic voters. Bloomberg aides believe even his support from African-Americans may turn to mush in the event — entirely possible under current polling — that he barely registers in the Iowa caucuses and performs limply in the New Hampshire primary.

At the same time, the assumption is that South Bend Mayor Pete Buttigieg is riding high in Iowa largely because he has devoted so much personal time there. It's an investment that may pay off with a victory there, the thinking goes, but won’t translate into national gains as Democratic voters conclude at age 37 he is too young and inexperienced to actually win.

Bloomberg aides say the former mayor likes and respects Warren personally, and is not bothered by the effect of her wealth tax proposals on his own fortune. The problem, they believe, is that she made a critical strategic error by deciding no rival would get to her left, and in the course embraced a “Medicare for All” plan in which private insurance would be banned. The plan is losing popularity among Democrats, and many party officials share Bloomberg’s belief that the plan could be her undoing in a general election.

“We did a poll, it was the exact same poll that the New York Times did — it overlapped by a few days — and it had Elizabeth Warren losing not one swing state but six swing states,” one of Bloomberg’s advisers said, listing the states as Florida, North Carolina, Pennsylvania, Michigan, Wisconsin and Arizona. "If the election was held today, with her [running] against Trump, he wins all six" states, the person added.

Bloomberg aides say they are helped by Democratic voters’ eagerness to put head before heart in 2020. His recent polling has shown that 85 percent of Democrats rank perceived ability to beat Trump as a top concern, a number that has spiked 40 points or so since the impeachment drama got underway in September

These aides don’t disguise their hope that Warren will do well enough to serve as a foil but not so well that she is the prohibitive favorite by March 3. They want Warren and Sen. Bernie Sanders to each keep enough support that the battle for the Democratic left remains a stalemate.

Yes, but: There are a lot of questionable assertions in the Bloomberg team’s appraisal of the race. Is it really so clear that Biden is spiraling downward? A new national Quinnipiac poll showed he just retook the lead while Warren lost half her support, dropping to third place. Journalists have been quoting Democratic chattering-class types for months about his alleged defects, but he continues to perform well in national polls and his support among African-Americans especially has proven durable. The primary is littered with candidates mired in single digits in the polls because they anticipated a Biden collapse that never came.

What’s more, primary candidates often look weak as general election contenders at this stage in the calendar. Historically, early victories have transformed how they are perceived by the electorate. The assertion that 2020 will be different is a wish by Bloomberg’s team but so far it is only that. In addition, women voters especially will remember that “too liberal, hurting our chances of victory” was also the rap against Nancy Pelosi, who led Democrats to take back the House in 2018.

Assumption: Bloomberg has a wide open country to portray himself as a winner

While the alleged losers are strapped down doing their thing in Iowa ( Feb. 3), New Hampshire ( Feb. 11), Nevada ( Feb. 22) and South Carolina ( Feb. 29), the man who ducked those contests is ready to spend hundreds of millions on ads and campaign turnout apparatus in Super Tuesday’s 15 states, plus more than a dozen other states and territories later in March.

It can’t be emphasized enough how unusual this strategy is. Successful nominating strategies have always started with early small-state victories, and then gone national. If one was going to try a different national-first strategy, it would help to have a self-funded campaign backed by a fortune (estimated $54 billion) that is several dozen times larger than Trump’s.

Yes, but: There may be good reason, beyond just limited financial resources, this has never been tried before. It is unproven whether a candidate can simply buy credibility with national voters through advertising if he has skipped the first states. It also might overestimate the effect of paid media and undervalue the impact of earned media from early-state victories. If Bloomberg has got thick enough skin to withstand the caustic dismissals of other candidates, and media mockery that will come if the strategy doesn’t work, he has nothing to lose in the experiment except a small fraction of his fortune.

The assumption: Biography can beat ideology

Bloomberg is not going to run principally as “a centrist” who thinks Warren and Sanders are “too liberal,” even though both things happen to be true. A message of someone who likes his porridge neither too hot nor to cold has already flopped for several candidates (Michael Bennet and John Hickenlooper) and hardly fits with the disruptive mood driving politics in both parties.

At least initially, advisers say, Bloomberg hopes he doesn’t even have to launch direct criticism of Warren or other candidates.

Instead, he’s counting on two things. The first is that his personal life story as someone who started “as a middle-class kid” — as his first, newly released ad puts it — and then built the Bloomberg media empire before becoming mayor of New York shortly after 9/11, is compelling to a national audience that otherwise would not much identify with a rich New Yorker.

“We have a really compelling candidate with a really compelling message and life story and a lot of resources to share that message with a lot of people,"said adviser Howard Wolfson, "and that’s not about running against any other one person.”

The second is that his national leadership on gun control and climate change position him as sufficiently bold on the most important issues to appeal to progressives. In addition, not many candidates boast about their record of raising taxes, but that is what Bloomberg is doing now as the former Republican shores up his liberal bona fides.

Some Bloomberg advisers say they would, as a matter of personal interest, welcome a genuinely searching philosophical debate between Bloomberg and Warren on the role of capitalism and wealth creation, which Bloomberg believes in and Warren thinks too often hurtles into pure greed. It would feature two informed and articulate advocates for different points of view.

For now, however, they are trying the rather complicated feat of saying Warren may be unelectable while not offending her supporters and not looking like they are being condescending toward a strong woman.

Yes, but: Bloomberg’s biography is impressive, and his new ad making the case is polished. But this may be a case of telling rather than showing. In person, Bloomberg is hardly a commanding presence or electrifying speaker. As for their notions about how to run against a woman, if you are worried about being condescending there is a good chance you may indeed sound condescending.

The assumption: His people are smarter than the average bears

They may be crazy, they may be brilliant, but in any event the people around Bloomberg’s campaign have been around the block. It includes long-term advisors like Sheekey, a Washington native who started on Capitol Hill in his 20s and eventually became chief of staff to Sen. Daniel Patrick Moynihan, and also Wolfson, who ran the Democrats' House campaign arm in the early 2000s and then ran communications for Hillary Rodham Clinton’s first presidential campaign.

It also has old Bill Clinton advisers with centrist streaks like pollster Doug Schoen and ad maker Bill Knapp. The team is also quickly expanding to include respected regional operatives like Ryan Berni, a former deputy mayor of New Orleans who’s in talks with the Bloomberg campaign to help carry Louisiana and hire operatives in states that are often overlooked in primaries.

The Bloomberg team believes his efforts on behalf of House Democrats in 2018 helped him build technological capacity and expertise in identifying and mobilizing voters that is superior to his rivals. More broadly, Democrats in recent cycles have fallen behind in the data wars against Trump, with his ability to efficiently enlist supporters for fundraising and turnout without spending (as weaker candidates must) vast amounts of money simply to identify potential backers. Bloomberg’s team is boasting that he will close the gap.

Yes, but: Lincoln said that the hen is the wisest of all animals, “because she never cackles until the egg is laid.” Of course, Bloomberg’s team needs to do some boasting now just to be taken seriously by Democratic activists, who in these hyper-political times are following campaign coverage closely. The next four months will show how well Bloomberg’s team can match their ability to articulate a winning strategy with an ability to execute a winning strategy. Even Bloomberg’s team acknowledges they’re not completely sure that this strategy will be more of a golden egg or a goose egg.