The 5 big 2020 fights to watch this week, ranked

With 86 days until the Iowa caucuses, the 2020 election will be here before you know it. Every Sunday, I will outline the 5 BIG storylines you need to know to understand the upcoming week on the campaign trail. And they’re ranked — so the No. 1 story is the most important of the coming week. 

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5. Bloomberg vs. the calendar: The former New York City mayor has two calendar questions surrounding his potential candidacy.

First, did he get in too late? Yes, Michael Bloomberg qualified for the presidential ballot in Alabama on Friday. But can he meet the varied ballot requirements — many states requires slews of signatures that take time and money to get — with such a truncated timeline? The best argument in Bloomberg’s favor is that he’s a billionaire and can throw loads of money at these ballot problems as they arise. Which, maybe?

Second, can any candidate — even one worth $50+ billion — skip the first four states (Iowa, New Hampshire, Nevada and South Carolina) as Bloomberg would do if he ran and have a real chance at winning? It hasn’t worked before in the modern nominating era, largely because momentum is built in those first few contests that carries over throughout the rest of the primary.

For Bloomberg to avoid that fate, he needs some help. A single candidate — like, say, Massachusetts Sen. Elizabeth Warren — winning several of the first four could give her enough momentum to make Bloomberg’s plan useless. What Bloomberg needs is a muddled result out of the first four states — ideally with three (or even four) different winners. That would mean a reset of the race in early March, when Bloomberg begins to factor into the race in earnest.

4. Buttigieg vs. everyone else: The New York Times headline on Sunday tells it all: “Why Pete Buttigieg Annoys his Democratic Rivals.“

What’s behind the disdain of Mayor Pete held by his opponents? A decent chunk of it is jealousy; Buttigieg has raised more money and performed far better in polls than most of the field and is seen by lots of people within the party as its future.

The other piece of the annoyance is rooted in the confidence (some would say over-confidence) of the South Bend, Indiana, mayor and his team. Buttigieg, much more so than the rest of the field, is willing to publicly play pundit and make pronouncements like he did last week when he said the race was now down to him and Warren. (He later walked that back.)

What that rising ire means for Buttigieg is, well, watch out. Buttigieg is likely to be a major target in the November 20 presidential debate — and in the 10 days between now and then, too. The likeliest attacks? His age (he’s 37), his inexperience (he’s only ever served as the mayor of South Bend) and his lack of detailed policy plans.

Buttigieg’s ability has been the story of the race so far. Can he fend off the inevitable attacks that come with his rising poll status?

3. Warren and Sanders vs. Bloomberg: The likely late-entry candidacy of Bloomberg has made Elizabeth Warren and Vermont Sen. Bernie Sanders very, very mad.

“Tonight we say to Michael Bloomberg and other billionaires: Sorry, you ain’t gonna buy this election,” Sanders told a cheering Iowa crowd Saturday night. Warren sent a tweet with a link to her billionaires calculator that tells the uber-rich how much more in taxes they would pay under her presidency than they do right now.

The willingness of the two most liberal candidates in the race to attack the richest person in the race (assuming Bloomberg runs) is telling — especially when you consider that both Warren and Sanders have avoided directly attacking their rivals in the race to date. (More on Warren dipping her toe further into the attack waters below.)

Warren and Sanders clearly believe that a Bloomberg candidacy is good news for them — further dividing the moderate/pragmatic/establishment vote between Biden, Buttigieg and now Bloomberg. While Bloomberg is an imperfect example of the ways in which the ultra-wealthy game the system — he donates huge sums to both charities and political causes — his defense of the business world is enough for both Warren and Sanders to jump on him.

Watch to see how Bloomberg hits back — and if it works.

2. Trump vs. the public: The President has, to date, cast the impeachment investigation led by House Democrats as a “witch hunt” and a “hoax” among other things. Those attacks have been interspersed by the regular release of transcripts of witnesses who have testified behind closed doors about the July 25 phone call between Trump and Ukrainian President Volodymyr Zelensky — transcripts that paint a clear picture of a pressure campaign organized by the White House to force the foreign power to open an investigation into Joe Biden. (There is no evidence of wrongdoing by the former vice president.)

The landscape of that fight changes on Wednesday, when the House holds its first of a series of open, public hearings with US diplomat Bill Taylor on Wednesday. (Taylor is one of three witnesses expected to testify publicly this week.) The open hearings pose an entirely different challenge for Trump since visuals are always more powerful than words on paper.

Trump, of all people, understand this; he has spent a lifetime using the power of TV to his advantage. But shaping how people perceive these public hearings is largely out of his hands. He can tweet, sure. He can attack everyone as “Never Trumpers” — despite no evidence that that’s the case.

What will mater most, however, is how credible people like Taylor and George Kent, a State Department official, come off to the public. And whether the moments created in these hearings — and there are always moments — work in the President’s favor or in the favor of his opponents.

1. Biden vs. Warren: When Warren suggested the former vice president should be running in the Republican presidential primary because of his criticism of her “Medicare For All” plan, Biden fought back.

He’s spent the past week bashing Warren as an elitist who is out of touch with working people, who, he maintains, are the core of the Democratic Party. Warren has cast that elitist attack as an attempt to paint her as angry — a gendered low blow. “Over and over, we are told that women are not allowed to be angry,” Warren wrote in a fundraising email to supporters. “It makes us unattractive to powerful men who want us to be quiet.”

Both sides clearly believe that this is a fight that benefits their side — and that they can win. Which means it’s not going to stop anytime soon.

To reclaim momentum in the race, Biden has to convince Democratic voters that Warren represents a dangerous gamble because of her liberal policies and alleged elitism. For Warren, she needs to show she can beat back that attack — which will surely come from Trump if he is the nominee — while also making the case that Biden’s hits on her are a function of the establishment (and men in particular) panicking because they see a strong woman emerging as the potential nominee.