A strategic guide to navigating the law like Donald Trump

Winners cannot lose.
Winners cannot lose.
Image: Reuters/Joshua Roberts
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US president Donald Trump isn’t a lawyer, but he certainly navigates the law like a boss. Trump’s approach is counterintuitive, and not for the poor or faint of heart. But it’s also effective: By embracing precisely the kind of trouble that others shirk, he manages to get away with saying and doing far more questionable stuff than your average Joe—or president.

Take one of Trump’s most notorious declarations, a March 4 tweet alleging that, during the campaign, then president Barack Obama wiretapped Trump Tower.

That claim has since been widely debunked—on March 20, FBI director James Comey testified before Congress that there is no evidence to support it, and lawmakers on both sides of the aisle have also denied it. But none of that has convinced Trump.

The president has issued dubious Twitter salvos with lower stakes, too. For example, he called Hillary Clinton the most corrupt candidate ever (a tweet accompanied by a Star of David) and described former Fox News journalist Megyn Kelly as a lightweight reporter. But the claims about Obama constitute accusing a sitting US president of a crime. LawNewz noted that legal experts say Obama even “has a strong case for a libel lawsuit.”

Libel in a world without truth

Technically speaking, it’s true that Obama may have a case. But technically doesn’t mean realistically, at least not when it comes to Donald Trump. Outrageous claims are his specialty, and Trump is the master of staying legally circumspect while appearing to be publicly reckless.

Libel is defined as a written published statement that is false and injurious to the reputation of another. To prove libel against a public figure, the statement has to have been made with both “reckless disregard for the truth” and “actual malice.”

Richard Painter, former ethics counsel to US president George W. Bush, told LawNewz that “an accusation of illegal wiretapping… would likely be criminal if a government official ordered it. Accusing someone of a crime is actionable as libel.” Painter noted that the “actual malice” standard is clearly met in this situation, and that Obama could sue Trump for his defamatory words.

To defeat such a suit, Trump would have to show he didn’t act maliciously and didn’t know what he said was false.

The latter might be difficult. In January, the New York Times reported on an investigation of Trump’s ties to Russia that did refer to wiretapping. As John Crudele noted in the New York Post last month, “That story didn’t go as far as to claim what Trump did: that he was wiretapped in Trump Tower — by President Obama. But [it] does make Trump’s accusation look a little less crazy.”

Ironically, Trump tweeted this about Crudele’s story:

You’re the puppet!

Any ambiguity surrounding Trump’s beliefs or intentions is crucial from a legal perspective. The president makes outrageous statements regularly, and takes them back whenever it’s clever. Being bombastic is standard practice for Trump, which makes it difficult to show he acted disingenuously, or with malice, in any particular instance. Playing loose with facts and attribution—and liberally accusing publishers of peddling “fake news”—likewise makes it easy to argue that he didn’t know what was said was untrue.

Herein lies one part of Trump’s legal genius: If everything you say is outrageous, then really nothing is. What’s a reckless disregard for the truth when we can’t agree on what truth is anyway?

There’s proof that this approach actually works for Trump in the context of defamation. In January, before he assumed the presidency, Trump defeated a libel claim filed in New York state court by Cheryl Jacobus, who he said in a tweet turned “hostile” after he denied her a job that she “begged” for. The judge wrote of Trump:

His tweets about his critics, necessarily restricted to 140 characters or less, are rife with vague and simplistic insults such as ‘loser’ or ‘total loser’ or ‘totally biased loser,’ ‘dummy’ or ‘dope’ or ‘dumb,’ ‘zero/no credibility,’ ‘crazy’ or ‘wacko’ and ‘disaster,’ all deflecting serious consideration…Indeed, to some, truth itself has been lost in the cacophony of online and Twitter verbiage to such a degree that it seems to roll of the national consciousness like water off a duck’s back.

In other words, Trump’s tweets—both substantively and in terms of volume—make it difficult to take him seriously, which works in his favor. Speaking to the Financial Times about his Twitter habit (paywall) on April 2, Trump said, “You know, if you issue hundreds of tweets, and every once in a while you have a clinker, that’s not so bad. Now my last tweet, you know the one that you are talking about perhaps, was the one about being in quotes wire tapped, meaning surveilled. Guess what, it is turning out to be true.”

Playing perpetual hardball

If the key to Trumpian legal maneuvering is constantly flooding the zone, it’s no surprise that Trump is embroiled in a lot of lawsuits.

In just the first two weeks of his presidency, Trump policies were at the center of 50 lawsuits. Between 1983 and 2015, Trump himself was a party in about 170 federal lawsuits, LawNewz reported. That figure doesn’t account for foreign court matters or any state cases, and reflects a fraction of the legal action Trump saw during that period. Yet the publication noted that this collection covered numerous areas of law and read “like a history of Trump’s business failures, successes, and bombastic personality.”

USA Today reported last July that Trump had been involved in 3,500 state and federal cases over three decades, calling him a “fighter” who “sometimes responds to even small disputes with overwhelming legal force…[This] analysis shows that lawsuits are one of his primary negotiating tools.”

Trump’s approach isn’t necessarily the most efficient—as of March, the White House’s 26-person legal team was already larger than during the first six months of Obama’s tenure. Above the Law said of the Trump White House Counsel team: “It would be hard to find a more high-powered collection of two dozen attorneys in any law office.”

That’s no accident. When deep-diving into trouble is how you stay out of it, clever lawyers are a necessity.