After skipping Iowa and New Hampshire, can Michael Bloomberg win the Democratic nomination?

After the farcical events of the Iowa caucuses, the New Hampshire primary has finally introduced some order into the Democratic primary.

Bernie Sanders and Pete Buttigieg are duking it out at the top, Amy Klobuchar’s strong third-place finish has vaulted her towards frontrunner status, and Elizabeth Warren and Joe Biden are rapidly falling behind. Entrepreneur Andrew Yang has dropped out, while billionaire Tom Steyer is staking his chances on Nevada and South Carolina.

But however much the next two contests winnow the field down, the contenders have another adversary to face: Michael Bloomberg, the almost unimaginably wealthy former mayor of New York who’s spent tens of millions of dollars on his campaign even as he’s entirely skipped the early primary states.

Once thought highly unlikely to run and then written off as a vain sideshow, Mr Bloomberg has hired hundreds of people across the country and spent hundreds of dollars on crucial TV advertising. He has yet to make it into a Democratic debate, but looks likely to finally reach the polling threshold that would guarantee him a place in the next one.

The first big day in his campaign is March 3 — aka “Super Tuesday” — when 16 contests are held at the same time. It’s in these states that Mr Bloomberg has concentrated much of his spending and organising.

His plan is to enter the race with a bang and start blocking the other candidates’ paths to the nomination after they've expended vital resources fighting each other in the first few states.

So what are the odds Bloomberg’s strategy will work — and how could he fail?

First of all, by the standards of typical presidential campaigns, his chances are unusually hard to predict. Because no one in modern US political history has tried what Bloomberg’s trying on such a vast scale, even the country’s crack pollsters are wary of predicting his chances.

Even as he announced that Mr Bloomberg is now included in FiveThirtyEight’s forecast, the legendary Nate Silver cautioned against taking current predictions seriously: “Suffice it to say that I think there’s sometimes a lack of rigour when analysing Bloomberg’s chances,” he wrote. “Self-funded candidates are rare enough, but a self-funded candidate with as much money as Mr Bloomberg who’s prepared to spend that money in these quantities is unheard of.”

“In some simulations, the model treats Mr Bloomberg’s enormous spending as a relatively important factor in the race, and in other simulations, it gives it very little weight,” Mr Silver says. “This reflects the fact that the evidence is quite mixed on how self-financed candidates do as compared with candidates who raise money from individual donors.”

There’s also another variable to consider: the particular states in which Mr Bloomberg is investing.

His biggest single target is California, which votes on Super Tuesday and where he has spent vast sums of money even by his own standards.

After holding one of the later primaries in 2016, California’s role in this year's nominating process has been talked up ever since it moved its date forward into February. It carries the most delegates of any state, and could theoretically offer one candidate a massive, even decisive, advantage.

“Theoretically”, however, is the key word. California allocates its delegates in a complex way that makes it very hard for one candidate to come out with a massive net gain over their rivals — especially in a contest with more than two viable contenders.

If Mr Bloomberg fails to rack up a net delegate advantage by running strong in the largest states, he will miss a crucial opportunity to overtake the other contenders. However, he’s also fighting on another front: the smaller states that start voting from Super Tuesday onwards.

Many of these are states where the Democrats rarely, if ever, seriously compete to win in presidential years. That means the party’s infrastructure on the ground is relatively thin, and that candidates must therefore invest heavily to build machines of their own. Given the sheer expense of competing in the early states alone, most of the campaigns have directed their spending and hiring at established battlegrounds.

Mr Bloomberg has taken the opposite approach. Skipping the first four contests entirely, he has poured money into hiring and organising for often-overlooked states like Oklahoma and Alabama, where strong finishes could net him a serious delegate advantage over whoever’s still in the race by the beginning of March.

This isn’t so unlike the strategy that worked wonders for Barack Obama in 2008, when he focused on winning big in places that Hillary Clinton’s campaign overlooked. By consistently defeating her by huge margins in small states like Idaho, he was able to eat into any net delegate advantage she gained from winning more narrowly in big states like Ohio.

But however well Bloomberg manages to execute that strategy, he’s still fighting an uphill battle.

As FiveThirtyEight founder Mr Silver writes, one thing is increasingly true: even if Bloomberg does manage to build up his delegate count from Super Tuesday onwards, there simply may not be enough delegates available for him to win. “The more you try to run through specific, realistic scenarios for exactly how Bloomberg wins the race,” said Mr Silver, “the harder you’ll find it is for him to get a majority of pledged delegates.” That leaves another path to victory: a contested convention.

Contested conventions are not common. The most recent that really qualifies is the Democratic one in 1980, when senator Ted Kennedy tried and failed to persuade delegates to abandon the incumbent president, Jimmy Carter; since then, no convention for either party has begun with any serious doubt about who the party’s nominee would be.

And yet, with a crowded field of credible candidates, this is a scenario that several of this cycle's campaigns are reportedly preparing for.

To seize the nomination at a contested convention, Mr Bloomberg (like any other candidate) would first have to win enough delegates to be a credible challenger, then probably persuade another campaign to release some of its pledged delegates to join his column and/or win over a good share of “superdelegates”, the party insiders who can vote on the nomination if the convention’s first ballot fails to produce a winner.

On that last point, Mr Bloomberg has to overcome a very serious obstacle: himself.

With Super Tuesday round the corner and his polling figures rising as planned, Mr Bloomberg is increasingly being attacked for his record as mayor, in particular his embrace of stop-and-frisk policing tactics. He credits the policy for bringing down the city’s crime rate, but it has for years been decried as the epitome of racism in law enforcement.

Just as the New Hampshire primary was wrapping up, an audio recording of Mr Bloomberg talking about stop-and-frisk began to recirculate online. In it, he voices exactly the ideas that his policies have long been accused of indulging:

“We put all the cops in the minority neighbourhoods. Yes, that is true. Why did we do it? Because that's where all the crime is … and the way you get the guns out of the kids' hands is to throw them up against the walls and frisk them."

These sentiments are a hard sell with the Democratic party’s electoral coalition, which is younger, more educated and more diverse than ever. Mr Bloomberg now claims that “my comments about [stop and frisk] do not reflect my commitment to criminal justice reform and racial equity,” but few on the left seem convinced — just as they are disinclined to listen to a billionaire whom they see as trying to buy the presidency.

As he now prepares to compete at the ballot box with Bernie Sanders, the risk is that his own words could put a permanent ceiling on his support, one that no amount of money might be able to lift.