Donald Trump's campaign is built around a simple, yet profound idea: Donald Trump is great. Arrogance isn't unusual in a presidential candidate—it's pretty much a prerequisite—but Trump is different because he doesn't really have any other ideas beyond his own greatness. His foreign policy is vague at best, his healthcare proposal is mostly Republican boilerplate, and he tosses out promises both big and small like other 70-year-old men toss breadcrumbs to pigeons.
Specifics and concrete plans are for politicians, and Trump is no politician. He's a winner who's going to make America great again. This is explicitly why his supporters like him. After speaking to some of Trump's richest backers, the New York Times Magazine's Adam Davidson summarized what they told him like so: "The specifics of his plans were beside the point, because Trump's proven instincts as a businessman were all that mattered." Basically, Trump will be a good president because he is good at everything he does.
The counterargument? The job Trump is currently doing most publicly—running for president—is a job that he appears to be doing very, very badly.
Trump is, of course, very popular, and many people come to hear him speak, though fewer people than generally show up for a Kevin Hart show. He's charismatic, he's beloved, he has a lot of nice suits, but those are traits—like an inflated ego and a few million dollars in cash—that all presidential candidates have. The actual work is duller, the way actual work always is: the hiring of staff, the managing of an operation that stretches across states, the coordination of an ever-growing organization as it responds to conditions that can change daily, if not hourly. This is stuff all politicians are required to do, or hire people to do, regardless of party or ideology. Stuff that, a successful businessperson like Trump should, in fact, be good at.
Well, turns out Trump is fucking up all that stuff pretty royally. On Monday, an MSNBC report quoted sources from inside his campaign who described the operation as "dysfunctional" and unable to perform basic tasks like announcing endorsements through press releases and issuing timely rebuttals of Hillary Clinton's speeches. Instead of having whole teams of people managing Trump's message, as most candidates do, MSNBC reported, it was just Trump and his Twitter account beefing with CNN and saying that Clinton was bad because she used a teleprompter.
This lack of organization really shone through in the case of Trump University. The problem isn't that Trump ran a business that seemed to be based off of persuading students to go into credit card debt so they could attend dubious real estate seminars. The problem isn't even that some of those students are suing Trump. Hey, these things happen—sometimes your business is accused of being a fraud, sometimes the FBI is investigating you because you kept some classified documents on your home server. The problem is that Trump's response has been to fall into a hole of his own devising, then keep digging.
Instead of some kind of coordinated media blitz from his supporters defending Trump University or at least maintaining that the suits were baseless, the candidate himself went around saying that the judge presiding over one case was biased because of his Mexican heritage. While Republicans criticized Trump's comments, he went a step further, saying that a Muslim judge would be biased against him too.
Then, after his own campaign sent out a memo to his top supporters telling them to stop talking about the lawsuit, Trump got on the phone and overruled it, saying that instead they should go after reporters asking those questions as the real racists. Then, not one but two of the people on that presumably fairly exclusive conference call told the whole embarrassing story to Bloomberg.
This sort of inside baseball story isn't likely to push voters, who I can't imagine care about the minutiae of messaging, to vote one way or another. Certainly, none of Trump's supporters give a shit—to many of them, no doubt, his lack of a communications staff just shows that Trump is his own man, virtuously untethered from elite DC BS. But it's telling that Trump managed to turn a story about how he was a fraud into a story about how he was a racist, and that his campaign is not just disorganized, but filled with people who will go to the press and complain about how disorganized it is.
It's clear Trump is bad at hiring people. He's also bad at reaching out to donors, a regrettable but necessary part of running for president. He's bad, too, at tailoring a message that appeals to anyone who isn't white, male, and angry. He's got conservative Latinos publicly complaining about the campaign's lack of outreach and minority staffers leaving the Republican National Committee en masse. All of that may not currently be hurting him in the polls (he is still enormously popular among white men), but it raises questions about how he's going to win. Is his campaign really going to succeed in getting disaffected first-time voters out to the polls in swing states? Is he going to get to a place where prominent members of his own party aren't denouncing the things he says as racist?
Clinton has her own obvious blind spots and scandals, and there will certainly be days and weeks ahead when Trump is on the attack, and she's on the defensive. But campaigns are about more than just the figureheads at the front. They're about the massive machinery behind them that moves voters to the polls. If that isn't well put together, Trump can say anything he likes, and he'll wind up a loser come November.
Follow Harry Cheadle on Twitter.