I didn’t wake up Monday morning intending for this to be “The Trump Campaign Is a Rolling Dumpster Fire Week” here at The Plum Line, but we follow where the news leads us. And the news for Donald Trump has transitioned from a series of stories about appalling things he has said to a series of stories about what a disaster his campaign is, at least for the moment. Today’s news comes in the form of a shocking Federal Election Commission report that was released last night. I’ll let Matea Gold and Anu Narayanswamy explain:

Presumptive GOP nominee Donald Trump loaned his campaign $2.2 million in May and collected $3.1 million in donations, ending the month with less than $1.3 million in bank, according to new campaign finance filings.
The real estate mogul’s meager cash flow spotlighted the urgent need for him to dramatically ramp up the fundraising he’s doing in conjunction with the Republican National Committee, a task he has fitfully embraced.
Trump’s small haul came as presumptive Democratic nominee Hillary Clinton continued to stockpile money: she raised more than $28 million in May and started June with $42 million in cash.

For the presumptive nominee of a major party to have only $1.3 million in the bank isn’t just unusual, it’s positively stunning. That figure is what you expect from someone running for a House seat, not someone faced with mounting a national campaign whose costs could approach a billion dollars. And this is a story about much more than money.

Let’s remember what the entire basis of the Trump candidacy is. Trump argues that he can fix America’s problems and make us great again. Why him? Because he’s rich, that’s why. That spectacular, tremendous, mind-boggling wealth is supposed to be proof of Trump’s innate brilliance, his superhuman negotiating skills, his unearthly management expertise. He might not be able to tell you the difference between Medicare and Medicaid or between the deficit and the debt, but he gets things done. If you doubt, just look at the size of his plane.

And now, piece by piece, that image is crumbling.

Trump spent decades working to build a brand that would be synonymous with success (which just happens to be the name of his cologne), and that’s what his supporters so often cite as one of the main reasons they’re attracted to him: He made all that money, he’s such a terrific businessman, so surely he can clean up Washington and do a great job on the economy. But now that he has come under more scrutiny than he ever faced before, the picture of Trump as a high-class magnate is being replaced with a different picture, one of a grifter always dancing one step ahead of bankruptcy court and concocting one failed scheme after another to separate people from their money.

And while we sometimes overstate the degree to which the management of a campaign is a test of how a candidate would run the country, in Trump’s case it’s an unavoidable analogy. With his lack of experience in politics, people might not have expected Trump to devise the best voter contact strategy or delegate management operation. But if nothing else, at least he should have been able to assemble and oversee a well-run organization and raise a lot of money. Instead, he’s failing at exactly the things he’s supposed to be so good at.

What are the practical effects of the financial advantage Clinton now enjoys? It may be a while before we know for sure. This FEC report only includes figures up until the end of May, so it’s possible Trump’s fundraising in June is going gangbusters and he’ll be in fine financial shape before you know it. He has also loaned his campaign $45 million so far, money he may not ever get back. Even now he protests that if he wants to, he can finance the whole thing, which may or may not be true (since he shrouds his personal finances in mystery, it’s hard to know).

But raising money isn’t going to get much easier. Think about how you’d feel if you were a big Republican donor considering whether to donate to Trump. You probably didn’t want him to be the party’s nominee in the first place. His campaign looks like a disaster. And yet he’s constantly saying he doesn’t need anyone’s money. So why would you break out your checkbook?

Trump is still counting on the media to save him. He doesn’t need as much money as a traditional candidate would, he believes, because of his unmatched ability to seize the attention of the media, leaving the Trump name on the lips of every TV watcher, radio listener and newspaper reader.

The problem with that strategy is that these days, media coverage of Trump consists largely of 1) him saying appalling things that turn off key segments of the electorate; 2) people criticizing him, even members of his own party; and 3) reports on more alarming stories from his past. And if you think we’ve seen the last of those, think again. At some point, there will be a reason for reporters to take a new look at things like the Trump Network (his vitamin-selling pyramid scheme), and it won’t be pretty.

One should never assume that the way things are in June is the way they’re going to stay until November. This may be just a period of bad news Trump will get past, then regain his footing. But when the entire rationale for your campaign rests on your ability to obtain and manage money, stories like the ones we’re now seeing about Trump are likely to stick in people’s minds.

What Donald Trump is doing on the campaign trail

U.S. Republican presidential nominee Donald Trump speaks at a campaign event at Trump Doral golf course in Miami, Florida, U.S. July 27, 2016. REUTERS/Carlo Allegri (Carlo Allegri/Reuters)