Christopher Aluka Berry / Reuters

When Donald Trump announced his candidacy last summer, he dedicated part of his speech to a project he’s been working at throughout his decades in public life: He proudly bragged about his wealth, declaring that his net worth was at least $8,737,540,000, adding the possibility that it may be as high as $9 billion or $10 billion.

That branding paid huge dividends in business. And it appeared to work in politics. After on-the-ground reporting at dozens of events for the presumptive Republican nominee, Benjy Sarlin and an NBC News data team found that the most common answer voters gave for supporting Trump was his financial independence:

“He can’t be bought,” Eleanor Crume, 72, said at a South Carolina rally. “He’s not going to be bought by the lobbyists.”

“He can speak his mind because he’s not backed by these donors who say what he can and can’t say,” Travis Klinefelter, a 39-year old Iowa nurse, said.

“He’s not bought and paid for by special interests,” Dominic La Rocca of Ft. Lauderdale, Florida said. “Insurance companies, the banks, they get the law that they want.”

Inveighing against illegal immigrants and political correctness, Trump wins over some voters but inevitably loses many others. But branding himself as a rich winner? That’s the one aspect of his candidacy that appealed to his supporters without turning anyone off, even as it contrasted nicely with Hillary Clinton taking money from big Wall Street banks, foreign regimes, even the dread Donald Trump!

That’s why Trump’s recent behavior is so baffling.

“The Donald Trump campaign sent its first ‘emergency’ fundraising email to supporters Saturday, seeking to raise at least $100,000 by the end of the day,” The Hill reports. “That request follows a multimillion-dollar ad blitz launched by Hillary Clinton.”

The article quotes the solicitation: “Right now we're facing an emergency goal of $100,000 to help get our ads on the air," it said. "We need your contribution by 11:59 P.M."

Has any campaign email ever been so off-brand?

The recipient cannot help but feel cognitive dissonance. Hey, wait a minute, if he’s worth $9 billion dollars, if he’s as rich and successful as he says, why is it an “emergency” to raise what amounts to a rounding error in his net worth, by midnight no less?

I know where my mind goes. Is he so tightfisted and greedy that he’s lying to spur donations he doesn’t need from his working class supporters? Does he have much less money than he led his supporters to believe back when he promised to self-fund in the primaries? Is he fearing a massive financial hit if or when the Trump University lawsuit is litigated? Does he just not care very much about the general election?

It’s hard to imagine that the Trump campaign wants its supporters to draw any of those conclusions, but I find it hard to formulate a more charitable explanation that’s plausible. The implausible: He’s decided in a moment of introspection that he’s not qualified for the office he is seeking and is now quietly self-sabotaging to save face. Or perhaps he’s going to drop a billion dollars into his campaign coffers any day now?

If not, I’ll remain baffled by his approach.

On Monday, related news broke. The New York Times reports that the Trump campaign is facing the largest financial disadvantage in recent presidential history:

Mr. Trump began June with just $1.3 million in cash on hand, a figure more typical for a campaign for the House of Representatives than the White House. He trailed Hillary Clinton, who raised more than $28 million in May, by more than $41 million… The Trump campaign has not aired a television advertisement since he effectively secured the nomination in May and has not booked any advertising for the summer or fall. Mrs. Clinton and her allies spent nearly $26 million on advertising in June alone, according to the Campaign Media Analysis Group...

Mr. Trump’s fund-raising for May reflects his lag in assembling the core of a national finance team. In the same month that he clinched the Republican nomination, Mr. Trump raised just $3.1 million and was forced to lend himself $2 million to meet costs. Some invitations to Trump fund-raising events have featured the same short list of national Republican finance volunteers regardless of what city the event is held in, suggesting Mr. Trump has had some trouble lining up local co-hosts.

Even here, Trump did not decide to spend $2 million on his campaign (leaving him with a mere $8.73 billion by his accounting). He loaned his campaign the money, meaning he’s holding out hope that he can reimburse himself with future donations. Meanwhile, his inability or unwillingness to raise money or contribute to his own campaign threatens to do serious harm to the GOP’s down-ballot prospects:

In a first for a major party nominee, Mr. Trump has suggested he will leave the crucial task of field organizing in swing states to the Republican National Committee, which typically relies on the party’s nominee to help fund, direct and staff national Republican political efforts.

His decision threatens to leave the party with significant shortfalls of money and manpower: On Monday, the party reported raising $13 million during May, about a third of the money it raised in May 2012, when Mitt Romney led the ticket.

No wonder some Republican Party insiders are making another late push to dump Trump as the GOP nominee: They were expecting a Sugar Daddy and got a moocher.

There is one detail in the New York Times account that suggests Trump’s next round of financial disclosure forms will show more cash on hand. “Allies of Mr. Trump say they believe the tide is already turning,” the newspaper noted. Rather than self-funding, “On Tuesday, Mr. Trump will appear at a high-dollar fund-raiser in New York City hosted by some of the most prominent names on Wall Street.”

That’s no surprise, given that he hired a former hedge-fund manager with ties to George Soros and Goldman Sachs to help run his campaign. Still, it’s a huge gamble.

Will it cost Trump the votes of people like Eleanor Crume of South Carolina, who said that he couldn’t be bought; or Travis Klinefelter of Iowa, who said Trump is “not backed by these donors who say what he can and can’t say;” or Dominic La Rocca of Ft. Lauderdale, Florida, who said that “he’s not bought and paid for by special interests... Insurance companies, the banks, they get the law that they want”?

It’s one thing to prefer Trump to Clinton if you think he’s independent and she’s bought and paid for, but few will prefer him to her if, alongside all his other faults, they also see him as beholden to big donors just like the establishment he is running against. It seems to me that, if he really wants to compete for the White House, substantial self-funding is a no-brainer. Maybe he isn’t nearly as rich as he’s led us to believe.

Or maybe Donald Trump is just tired of winning.

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