Michael Kruse is a senior staff writer for Politico.

To keep hidden the details of his long-clandestine finances, Donald Trump has been waging a legal war wildly unusual for a commander in chief. He and his allies and associated business entities have sued two big banks he did business with plus Trump’s own accounting firm as well as the Democratic chairman of the congressional oversight committee. So far, federal judges have rejected these lawsuits, and Trump’s attorneys have appealed to keep the cases going.

These tactics, testing the limits of the separation of powers that underpin the government of this country, have been called “outlandish” in Congress. To those, though, who have followed Trump’s career, they’re nothing if not predictable. For nearly half a century, Trump, 72, has used lawsuits as cudgels and prods and publicity stunts. He and his wingmen have used them, or threats of them, to harass, to deflect and delay, to punish opponents and protect his brand, his money, his image, himself. Even in the face of losses, he has used them to find a way to wins.


The difference now is that Trump’s legal arsenal includes not just an array of personal attorneys but the vast resources of the Department of Justice—which at times he has hoped would serve the same role as his most bare-knuckled advocates. He is fighting personal legal battles that have ramifications today and potentially well into the future for the nation’s most important public office. Apples-to-apples numbers on this front are hard to come by, according to experts on the presidency and the judiciary, but scholars are confident in stating that Trump (with the possible exception of Richard Nixon) is unique in this regard. “I know of no president who was so openly combative and willing to sue and be sued,” said presidential historian Robert Dallek, who is working on a book called How Did We Get Here: From TR to Donald Trump.

The people who have known him the longest are not surprised in the least. “He sues,” said Barbara Res, the Trump Tower construction manager and a former executive vice president of the Trump Organization. “That’s his M.O. He sues.”

“It’s just another tool in his war chest,” said Jack O’Donnell, the former president of the Trump Plaza casino in Atlantic City, New Jersey. “He uses it to wear people out, whether it’s financially or emotionally.”

“He’s used litigation historically to keep hostile forces at bay and to delay reckonings,” Trump biographer Tim O’Brien said. “He’s also used it to try to embarrass competitors, critics or opponents. And I think by and large he’s done that successfully. He’s the poster child for the abuses and inefficiencies of the American court system.”

But can it work in this new venue? “That,” O’Brien said, “is the question that’s being tested right now: Is Donald Trump, as president, above the law?”



***

He’s not above the law. He’s just using it like any other citizen can, and should. That’s the view, at least, of Alan Dershowitz, the Harvard Law professor emeritus and frequent Trump defender. And it might even serve a useful political function.

“Bringing lawsuits is a way of invoking the system of checks and balances,” Dershowitz said, “and presidents historically have brought lawsuits, have responded to lawsuits—it’s a way of bringing the judiciary into the system of checks and balances that are tripartite in nature.” He called “reasonable” litigation “a perfectly appropriate use of the system of checks and balances.”

If nothing else, Trump has had an abundance of practice. His exhaustive history of weaponizing the courts started in 1973, when DOJ sued Trump and his father for racist rental policies in their fiefdom of outer-borough apartment buildings. Trump responded by hiring Roy Cohn, the notorious judicial and political fixer who’s been called “pure evil,” “a legal executioner,” and “one of the most despicable people in American history.” Cohn and Trump sued the feds right back—for $100 million. “The countersuit was bullshit,” said Elyse Goldweber, one of the prosecutors involved. But it extended the timetable of the case and turned it into a public relations skirmish as much as a matter to be settled purely in court. Nearly two years later, Trump and his father signed a consent decree pledging to change their ways, “one of the most far-reaching ever negotiated,” as DOJ put it. Trump, unchastened, insisted it was a win—a precursor to one of his most telltale maneuvers. Furthermore, for the government, the aftermath was galling. With Cohn at the point, the Trumps for years dragged their feet, exasperating subsequent prosecutors and effectively defanging the enforcement of the decree. As a whole, it would prove to be a singular font of so much of what was to come.

“Trump claims he went to Wharton business school,” presidential historian Doug Brinkley said. “What he did was attend Roy Cohn University.”

“Everything Trump does is steeped in Roy Cohn’s mentoring and teaching,” Cohn cousin David Lloyd Marcus said. “Roy knew that you could threaten to litigate, and that often that was enough. But also Roy knew that you could tie up things in the courts for years. Years. This is all right from the Roy playbook.”

A voracious pupil of the ruthless attorney, Trump has sued or been sued at least 4,000 times, according to the yeoman’s work of reporters from USA Today. He has sued people over unpaid royalties in licensing deals. He has sued Miss Pennsylvania. He has sued Bill Maher. He has sued the creator of Jeopardy! and Wheel of Fortune. He has sued Scotland. He has sued New Jersey. He has sued New York City, and he has sued New York state. He has sued Palm Beach. He has sued an architecture critic from Chicago. He has sued the secretary of the Interior and the National Indian Gaming Commission. He has sued people for using his surname in businesses … even though it was also their surname. He has sued and been sued by his first ex-wife. He has sued and been sued by Steve Wynn. He has sued and been sued by longtime business partners. “Just another lawsuit filed by Trump as a diversionary tactic,” a spokesman for one of those partners once said, “attempting to intimidate and to substitute publicity for substance.” He has threatened to file countless lawsuits he then hasn’t filed.

And legal documents show that when he has to give sworn answers, he is a grudging, hair-splitting deponent, performing his own versions of Bill Clinton-esque parsing. “Well, the word ‘developing,’” he once said in a deposition, “it doesn’t mean that we’re the developers.”

“I know lots about litigation,” Trump said in a speech at a get-together of the Nevada Republican Party in Las Vegas in 2011.

“Does anyone know more about litigation than Trump?” he asked at a campaign rally in January 2016. “I’m like a Ph.D. in litigation.”

“It’s a business for me,” he told Megyn Kelly that May, calling it a “tactic,” “and I have been successful—and I’ve, you know, used litigation, and sometimes I use it maybe when I shouldn’t, and sometimes I don’t.”

Last month’s lawsuit was not, for instance, the first time he sued Deutsche Bank. Back in 2008, he filed a suit against his most noted lender, attempting to wiggle his way out of $40 million of a construction loan he had personally guaranteed, worried he was staring at a catastrophe at the onset of the recession, taking the extraordinary legal position that the national real estate bust was an unforeseeable act of God, same as a tsunami or hurricane, that should void his obligations. It was, said one of the attorneys for the bank, “kind of crazy” and “kind of telling.”

“Every morning he wakes up and says, ‘Who can I sue?’” late public relations maestro John Scanlon once said.

“Anytime he thought someone was going to sue him,” Res said last week, “he would find a way to sue them first, because he wanted to be the plaintiff. He had this notion that if you were the plaintiff, you had a better chance of winning.”

There are, however, plenty of losses on Trump’s legal ledger.

He lost to the NFL. He lost to Marvin Roffman. He lost to Vera Coking of Atlantic City. And he lost to O’Brien, the biographer, whom he sued for reporting that Trump wasn’t worth what he said he was worth.

“He lost,” O’Brien stated bluntly. “Because the weight of everything was on our side. He routinely says publicly that he cost me a lot of money. He knows that’s not true. I didn’t pay a dime for any of that litigation. The New York Times’ lawyers were free to me, and my book publishers paid for outside counsel. And he knows he didn’t win that case. And he knows the results of choosing to litigate were far, far more damaging for him than for me.”

But O’Brien cautioned onlookers at this stage about reading too much into how that went down.

“That’s the exception, actually, in the long history of his litigation,” he said. “Most of the time he’s gotten the results he’s wanted.”



***

What was it that he wanted? To intimidate. To pay less. To save face by distancing himself from faltering projects. To fuel publicity. To buy time. To win in the longer run. For now, the Trump administration’s “win rate” in the federal courts is abysmal. The two recent suits he filed to block subpoenas for his records were summarily shot down, both judges ruling with unusual speed and dismissiveness. In these cases, if Trump was trying to delay, if he was trying to intimidate, it didn’t work. “It is simply not fathomable that a Constitution that grants Congress the power to remove a president for reasons including criminal behavior would deny Congress the power to investigate him for unlawful conduct,” one of the judges wrote, adding that Trump’s legal arguments had “fundamental” problems. At this, though, Dershowitz shrugged. “What’s important,” he said, “is what the courts ultimately decide, not how many lower courts go against him.”

“Contemporary presidents end up in court a lot, mostly regarding their interpretation of regulatory statutes,” said Texas A&M professor George C. Edwards III, editor of Presidential Studies Quarterly. “Trump is unusual in his blanket resistance to accommodating congressional investigations, which leads to numerous lawsuits.”

“This is another case where President Trump’s behavior is norm-busting,” added Russell Riley, a presidential historian at the Miller Center at the University of Virginia.

Trump has never had to grapple with this high a degree of scrutiny and interference. He also and equally notably has never had more power, and one of the primary ways in which he’s already a president of great consequence is that he has markedly altered the ideological makeup of the federal judiciary—up to and including, of course, the Supreme Court. And this is what people who know him the best think about when they think about Trump in his role as litigator in chief.

“I think he expects that the judges he appoints will help him one day,” said Michael D’Antonio, a Trump biographer and a CNN analyst.

“I think he believes that every suit he’s involved in will go to the Supreme Court and he will win,” Res said.

“Because he’s got the deck stacked,” O’Donnell said.

“I think,” O’Brien said, “unless institutions, particularly the law enforcement community and Congress, stand up for the rule of law, Trump is going to do an end run around people.”

“I think all he wants to do is get to November 2020,” said Carl Tobias, a law professor at the University of Richmond and an expert on the federal judiciary, “and he’ll be able to drag it out in the courts if he wants to.”

And it all traces back to the beginning. “He is using what he knows how to do best,” said veteran New York-based Democratic strategist Hank Sheinkopf, who’s been watching Trump for decades, “his knowledge of how to use the legal process and lawyers to stop his opponents from injuring him. And it’s worked. So why shouldn’t it work here?”

