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With just over 300 days until Iowa’s caucuses and more than a dozen Democratic candidates seeking their party’s nomination, it can all feel like a little much. 

So here’s my attempt to simplify it: Every Sunday night, I will deliver to your inbox the 5 BIG storylines you need to see to understand the week to come on the 2020 campaign trail. And they’re ranked – so the #1 story is the most important of the coming week. Subscribe to The Point newsletter here.

5. The health of Trump’s health care argument: Inexplicably, Trump (re)opened the health care debate last week, when his administration decided to support a Texas judge’s ruling that said the entire law should be invalidated. Despite Trump’s repeated pledges that “the Republican Party will become the Party of Great HealthCare!” it’s become abundantly clear in the intervening six days that there really is no plan just yet.

Senate Majority Leader Mitch McConnell (Ky.) was blunt about his plans on health care – putting the burden on Trump’s White House to offer details before he would take any action. Acting White House chief of staff Mick Mulvaney tried to compare the VERY broad outlines of health care to the approach the administration took on taxes, but the truth is that a GOP-controlled Congress wanted to pass a tax cut. A Democratic House does not want to upend the health care system.

This all feels like a BIG political mistake for Trump. And one that congressional Republicans don’t seem to be willing to help him fix.

Virginia Lieutenant Governor Justin Fairfax addresses the media outside of the capital building in dowtown Richmond, February 4, 2019.
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Virginia Lieutenant Governor Justin Fairfax addresses the media outside of the capital building in dowtown Richmond, February 4, 2019.

4. The Justin Fairfax question: You might have already forgotten about Fairfax, the Democratic lieutenant governor of Virginia who has been accused by two women of sexual assault. Fairfax denied those reports – and his camp says he has taken (and passed) two lie detector tests.

For the last month, the story has gone dormant. No longer. Both of Fairfax’s accusers are set to speak on TV in the coming days – which will push the issue back into the national media’s gaze. Most of the major 2020 Democrats have called on Fairfax to resign – advice he has, to date, ignored. With the story coming back on the radar, however, all of the candidates are likely to be asked about it again.

How do they handle it? Does Fairfax bend to the (increased) pressure? And if he doesn’t, what then for a party who has said women making accusations must be believed?

3. Beto goes to Iowa (again): O’Rourke seems committed – in Iowa, at least – to trying to recreate the formula that (almost) won him Texas in 2018: Go absolutely everywhere. Beto will spend four days this week – starting Wednesday – in the Hawkeye State. And that comes after O’Rourke kicked his campaign off in Iowa earlier this month.

It doesn’t take a political genius to see that Beto’s campaign has already made the decision to go all-in on Iowa which, I think, is a very smart strategy. O’Rourke’s strength is retail campaigning and Iowa is a retail campaign state. It also happens to be the first state that will vote in 2020 – and one that Barack Obama won back in 2008 to begin his march to the nomination.

The one downside of this Iowa bet for Beto? if he disappoints in the caucuses, that could be curtains for his campaign.

Democratic presidential candidate and former Texas congressman Beto O'Rourke speaks during his presidential campaign kickoff rally in Houston, Saturday, March 30, 2019.
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Democratic presidential candidate and former Texas congressman Beto O'Rourke speaks during his presidential campaign kickoff rally in Houston, Saturday, March 30, 2019.

2. Money, money, money: The first major marker of the 2020 race comes Sunday night at midnight, when the first fundraising quarter ends. Money – whether you like it or not (and lots of people don’t) – matters for two major reasons: 1) It speaks to real support as people who donate money to a candidate have truly invested in it and 2) Candidates need money to fund organizations, run TV ads, etc.

We expect BIG quarters from Sen. Bernie Sanders, O’Rourke and Sen. Kamala Harris – all of whom are regarded as top-tier candidates. (Sanders and O’Rourke raised around $6 million in their first 24 hours as candidates, which means they should have a very good first three months.)

South Bend Mayor Pete Buttigieg, who has been the buzziest candidate for the past several weeks, could keep that momentum up with a stronger-than-expected quarter. (Buttigieg is not a formal candidate right now; he has an exploratory committee.)

The most intriguing report to me? Massachusetts Sen. Elizabeth Warren, who underwhelmed in her first 24 hours of fundraising but has a massive haul – $11 million – she can transfer from her Senate account. She also just lost her finance director, which often spells trouble.

1. Joe Biden’s big trouble: The allegation leveled by former Nevada Lt. Gov. candidate Lucy Flores that, on the 2014 campaign trail, Biden kissed her on the head and made her feel “gross” and “confused” is a major MAJOR problem for the perceived 2020 Democratic frontrunner. Yes, Biden issued a denial – “Not once – never – did I believe I acted inappropriately” – on Sunday. 

But the problem for Biden is this: The Flores allegation isn’t in a vacuum. If you like Biden, who said himself Sunday has “offered countless … expressions of affection,” you see this as, broadly, part of who he has always been. He’s part of a different generation of politicians! He hugs everybody! If you don’t like Biden, you regard his behavior as unacceptable – and something that should have long ago been called out by the media and fellow Democrats.

Wherever you come down on that issue, we are now in a very different place culturally than even when Biden last ran for president in 2008. In an era of #MeToo, can someone like Biden – with an active allegation like this one from Flores against him – survive? And should he?