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The New York Times building (Photo by David Lat)

Since at least the 1980s, Donald Trump has had it figured out that if he does not pay his bills, everything more or less works out fine for him. Indeed, if a person has the resources and the malevolent willpower to resist legal efforts to collect on an amount owed, there are a million ways to delay, contest the underlying claim, and, if all else fails, shove the debt off onto some sacrificial business entity that is then sent swirling into bankruptcy. It’s often just not worth the fight against such an adversary.

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Of course, adherents to this strategy must lack even the most rudimentary ethical framework. Believe it or not, though, a sense of basic human decency has never seemed to stymie Trump.

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Even back in 2016 there already existed hundreds of unpaid judgments against Trump and his businesses totaling millions of dollars. Hundreds of liens filed against Trump, his companies, and his properties apparently proved an insufficient collections tool.

While stiffing a small HVAC company on a $75,000 bill is one thing, Trump has gotten himself into some real trouble lately. Small businesses have to make tough decisions about whether they want to spend more money on lawyers than they are likely to ever collect, or whether they instead want to keep their workers employed. The government does not have to face the same tough choices.

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Trump now lives under the shadow of a $355 million civil fraud judgment, which New York Attorney General Letitia James has vowed to collect upon immediately. In addition to having certain collections mechanisms at their disposal that might not be available to private creditors, the government also does not need to deal with the constant pressure of paying their own legal bills along the way. James might have better luck than the average citizen-litigant.

No surprise here: Trump has not paid the $355 million he owes (plus interest). He says he is appealing the ruling and is following his standard responsibility-dodging playbook.

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Same goes for the $83 million Trump owes E. Jean Carroll. He hasn’t paid any of it and has been griping about the size of the bond he’d have to put up to stay enforcement of the judgment during appeal. Although Carroll is certainly not the government, the size of her judgment against Trump, as well as the nature of the underlying meritorious claims, mean this debt isn’t simply going to go away or stagnate indefinitely like those owed to so many scorned contractors of decades past.

Even as the potentially existential nature of these sorts of cases is a new thing for Trump, general examples of Trump losing in court yet failing to pay what it has been determined he owes could fill volumes. In a truly stunning development, however, something recently took place that almost no one could have predicted: Donald Trump actually paid someone he owed money to.

Trump filed a bogus lawsuit against The New York Times and several of its journalists for publishing a Pulitzer Prize-winning reporting series about his finances. His suit was dismissed, and in January, Trump was ordered to pay $392,000 to The New York Times to cover the legal costs incurred defending against this lawsuit that the judge found to be frivolous and meant to silence journalists.

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Stick with me here, because this is where it gets really wild: on February 26, The New York Times confirmed that Trump had actually paid the $392,000 he owed.

What gives? It’s a fool’s errand to try to understand Trump’s thought process, though I would imagine plenty of people have been telling him lately that paying in order to close this front in his ongoing legal war would be a bargain at $392,000. Considering he spent $50 million on his own legal fees last year, $392,000 is a rounding error, and he’s got bigger fish to fry.

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Keep in mind too that we now know The Times has been paid, but we don’t know where Trump himself got the money. It’s entirely possible he found a way to pay The Times with money from his donors (Trump excels at spending other people’s money even when he won’t dip into his own pockets).

That being said, this is remarkable. It won’t become a pattern, but Trump paid money he owed without a fuss — and to The New York Times, no less! Just when you think you’ve seen everything, right?

Jonathan Wolf is a civil litigator and author of Your Debt-Free JD (affiliate link). He has taught legal writing, written for a wide variety of publications, and made it both his business and his pleasure to be financially and scientifically literate. Any views he expresses are probably pure gold, but are nonetheless solely his own and should not be attributed to any organization with which he is affiliated. He wouldn’t want to share the credit anyway. He can be reached at [email protected].

Topics

ATL Finance, Courts, Donald Trump, Finance, Finance Docket, Legal Fees, New York Times