Donald Trump Has a History of Not Paying His Bills. That Offers Some Insights Into His Personality.

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Presumptive Republican presidential candidate Donald Trump speaks at a campaign rally, May 25, 2016 in Anaheim, California.
Presumptive Republican presidential candidate Donald Trump speaks at a campaign rally, May 25, 2016, in Anaheim, California. Photo: ROBYN BECK/This content is subject to copyright.

USA Today has posted an explosive investigative story about what appears to be a deep aversion presumptive GOP nominee Donald Trump has to paying his bills. The short version: USA Today claims that, based on what looks like some rather impressive reporting, Trump has for decades looked for just about any excuse he could find to stiff everyone from plumbers to — can’t make this up — lawyers who represented him in non-payment lawsuits.

The longer version is something of a bloodbath for Trump: “At least 60 lawsuits, along with hundreds of liens, judgments, and other government filings reviewed by the USA TODAY NETWORK, document people who have accused Trump and his businesses of failing to pay them for their work,” writes USA Today’s Steve Reilly. “Among them: a dishwasher in Florida. A glass company in New Jersey. A carpet company. A plumber. Painters. Forty-eight waiters. Dozens of bartenders and other hourly workers at his resorts and clubs, coast to coast. Real estate brokers who sold his properties. And, ironically, several law firms that once represented him in these suits and others.”

The striking thing about Reilly’s article is that there’s no standard script for why a given person or company didn’t get paid in full by Trump — he seemed to withhold payment rather capriciously. While Trump would often claim shoddy work as his reason for not ponying up, Reilly presents pretty overwhelming evidence that in many, if not most, of the cases, this was not a credible claim.

Some of those cases, and the legal fallout that followed, are genuinely surreal:

Juan Carlos Enriquez, owner of The Paint Spot, in South Florida, has been waiting more than two years to get paid for his work at [a Trump golf resort called] the Doral. The Paint Spot first filed a lien against Trump’s course, then filed a lawsuit asking a Florida judge to intervene.

In courtroom testimony, the manager of the general contractor for the Doral renovation admitted that a decision was made not to pay The Paint Spot because Trump “already paid enough.” As the construction manager spoke, “Trump’s trial attorneys visibly winced, began breathing heavily, and attempted to make eye contact” with the witness, the judge noted in his ruling.

That, and other evidence, convinced the judge The Paint Spot’s claim was credible. He ordered last month that the Doral resort be foreclosed on, sold, and the proceeds used to pay Enriquez the money he was owed. Trump’s attorneys have since filed a motion to delay the sale, and the contest continues.

Enriquez still hasn’t been paid.

In another instance — one that staffers at a pro–Hillary Clinton super-pac are likely working into a YouTube spot as we speak, possibly as they high-five repeatedly — Trump allegedly withheld more than $83,000 from a Philadelphia cabinetry company that made “bases for slot machines, registration desks, bars and other cabinets at Harrah’s at Trump Plaza.”

The owner of the company was informed of this, Reilly reports, at a bizarre meeting with Trump during which Trump told him that, while he wouldn’t be paid fully for the work because of its shoddiness (despite the fact that the casino’s general contractor had already approved it), his company “could work on other Trump projects in the future.” In other words, Your work’s no good — let’s work together again sometime. The owner’s son told Reilly that the shortcoming was a major hit to the company, and that “[a]fter standing up to Trump … the family struggled to get other casino work in Atlantic City.” The company went bankrupt in 1989.  (It’s worth pointing out that this tendency of Trump’s is well-known among those who followed him closely over the years, and Trump himself had more or less bragged about it in some settings. But Reilly’s article appears to be the most detailed, damning recounting yet, and comes at a very vulnerable time for Trump.)

Politically, the obvious takeaway here is that these stories will make it much harder for Trump to present himself as a defender of the everyman. That act was always going to be an uphill battle for Trump in the general election given his pedigree, his wealth, and his affection for the gold-plated. But Trump had, to his credit, managed to overwhelmingly convince the GOP base that he was the guy to stand up for their interests at a time when economic insecurity is roiling countless Americans.

The problem is that many of the alleged victims of Trump’s underpayments look a lot like the folks whose votes he desperately needs for him to have any chance in November. Yes, the USA Today stories include instances in which Trump allegedly withheld money from waiters and high-powered attorneys — from working-class and upper-class folks — but many of the worst stories have to do with skilled laborers and contractors, with the sorts of people who are middle-class in theory but who have experienced increasing financial pressure and desperation in recent decades (as Nate Silver pointed out, the idea that Trump is driven primarily by working-class supporters is largely a “myth”). These people — the white ones, at least — are supposed to comprise Trump’s core bloc of voters. And now the next five months will feature countless tales of Trump appearing to screw them over, as journalists and oppo researchers dig deeply into the stories Reilly exposed. More stuff will come out, and some of it will likely be gruesome.

The USA Today story also adds an interesting new layer to the many attempts people have made to understand Trump’s personality — an irresistible parlor game given what a bizarre, unorthodox, and erratic candidate he has been, and the effortlessness with which he dispatched an infinitely more qualified, “professional” GOP field using some rather old-school bullying and explicit appeals to authoritarianism.

There are obvious perils to doing any sort of psych exam at a distance, so the usual caveats apply, but still: How can you not factor this into your view of who Trump is, deep down? The story line many people, myself included, had bought into has it that he is deeply narcissistic (a needy narcissist, perhaps), and therefore responds to any threat to his own inflated sense of his self-worth with absolute fury. This can explain his inability to let any criticism go and endlessly lash out at journalists on Twitter, to randomly bring up ostensible wrongs committed years ago, even when doing so is tactically foolish. It can explain the Gonzalo Curiel thing, for sure.

But this bill-paying stuff is different. It suggests a guy who views just about any interaction he has with anyone — even folks who haven’t wronged him, who are small-business people — as a chance to get one over on them, to get the better of the deal, to seize an unearned advantage (except to Trump, surely it felt earned because he was the one who seized it).

Trump talks constantly about his skill as a negotiator — he’s going to negotiate his way to Mexico paying for that wall; out of the trade deals that have, in his view, kneecapped the American worker; and to a more America-friendly NATO. It could be the case, though, that “negotiating” is just socially and politically acceptable Trump-speak for what really sits at the core of the Donald’s personality and his many ideas about how American policy should look: a deep, primal desire to dominate others in any conceivable way possible.

Trump Didn’t Pay His Bills for Decades