Donald Trump’s refusal to concede the presidential election and his attempt to challenge the results in the courts has unsettled many Americans, while dragging one of the world’s leading democracies on to unfamiliar terrain.

But to veterans of the New York City real estate world, the president’s actions since the November 3 election are familiar, and consistent with the playbook he honed for decades as a highly litigious property developer.

Among its core tenets: never admit defeat, even when you’ve lost; sue — preferably with big, bombastic claims — even if you don’t have much of a case; and hope that the resulting chaos unnerves adversaries or throws up other, as-yet-unseen, opportunities.

“A courtroom is a place where he is comfortable, for better or worse,” said a New York lawyer who had dealt with Mr Trump over the years. “He wins, he loses, sometimes he gets his ass kicked.”

But, the lawyer said, Mr Trump never concedes. “He can be falling to the mat at the end of the 15th round, and when the fight is over . . . he’ll be raising his hands in triumph, saying ‘I won the fight!’ and then, when the scorecard goes against him, ‘I was robbed! I want a rematch!’”

Michael Cohen — Mr Trump’s one-time fixer, who subsequently went to prison for, among other deeds, arranging payments to silence women who claimed to have had liaisons with Mr Trump — described the president’s blitz of election lawsuits and unfounded claims of voter fraud as “Roy Cohn on steroids”.

Mr Cohen was referring to the former chief counsel to Senator Joseph McCarthy’s anti-communist investigation committee, who tutored a young Mr Trump in how to use litigation as warfare while representing the Trump family business in a 1973 racial discrimination case brought by the Department of Justice.

The government accused the Trumps of refusing to rent apartments to black tenants. Rather than settle, Mr Cohn, who died in 1986, prodded Mr Trump to hit back with a $100m countersuit. 

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“He learned that the best defence is a good offence. And he learned that the way to do that is legally,” said a New York real estate executive who has tangled with Mr Trump. “I don’t think he ever had a particularly impressive track record of winning anything. But he was sufficiently litigious that it was a deterrent.”

Even in the litigious blood sport of New York real estate, Mr Trump stood out. In 2016 USA Today reported that Mr Trump and his businesses had been involved in at least 3,500 cases over the previous 30 years.

Mr Trump has sued everyone from his ex-wife to building contractors and tradesmen who worked on his luxury towers and casinos to the wealthy Hong Kong investors who bailed him out when he was overextended in the mid-1990s. He has even sued his lawyers.

“As it was then with bad faith lawsuits, so it is now,” said Barry Schreibman, a semi-retired real estate lawyer whose firm studiously avoided Mr Trump. “Although now the goal isn’t chiselling down a bill, the motive is the same: to make a profit from chaos.”

The president has acknowledged his zest for legal combat. At a campaign event in 2016 he quipped: “Does anyone know more about litigation than Trump? I’m like a PhD in litigation.”

Mr Trump’s propensity for lawsuits has intersected with an explosion over the last 20 years in election litigation in the US. Lorraine Minnite, a political scientist at Rutgers University, traces that to the Bush vs Gore dispute in Florida in 2000.

“It’s kind of the lesson the Republican party learned with the 2000 election. Which is, in a tight election, [if] you don’t like the results, you can shift the election contest into the courts,” Prof Minnite said.

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Few legal experts expect Mr Trump’s election lawsuits to successfully overturn the result, but there have been other occasions when litigation has snatched him a victory of sorts from what seemed like sure defeat.

In November 2008, the financial crisis was threatening a highly leveraged, 92-story Chicago tower that was running behind schedule. Deutsche Bank had given the Trump Organization an extension on a $640m loan that was overdue. Now it was demanding that Mr Trump personally repay $40m of the debt.

With his back against the wall, Mr Trump unleashed a legal complaint shot through with chutzpah. The developer accused his longtime banker of “predatory lending” and responsibility for the financial crisis as he demanded $3bn in damages. He did not win in court, but the parties eventually settled. Deutsche granted Mr Trump a further extension and later lent him more money.

His targets now are not banks or rival developers but the secretaries of state in Pennsylvania, Michigan and other swing states as he tries to have the election overturned, alleging irregularities and voter fraud. Several of his suits have been thrown out, and election lawyers see faint prospect that the president can deprive Democratic nominee Joe Biden of the White House. 

Still, there are other things short of victory that Mr Trump might hope to gain, say people who know him. Chief among them is protecting a brand that is built on the idea that he is the ultimate winner.

“I think he’ll drag it on and then he will find a way to claim that he’s doing this to heal the nation,” the real estate executive predicted. “Within a few weeks, he will announce his new television network or series or whatever he’s doing.”

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Asked if there was any circumstance under which Mr Trump would acknowledge defeat, the executive replied: “No! Oh, not at all. He will always claim to the end of his life that the election was stolen from him.”

Mr Cohen believed carrying on the fight was essential for the president to stir his formidable base — whether to keep a hold over the Republican party in the coming years, or to raise money for his political action committee and legal defence, or, as has been reported, to launch a conservative media network, or some other venture. 

“Donald Trump will never admit that he lost,” Mr Cohen said. “His claims of illegitimacy of the election is fundamental to his larger goals of establishing a shadow, for-profit presidency at [his Florida resort of] Mar-a-Lago.”

The lawyer believed Mr Trump’s supporters were encouraging his own pugilistic instincts, and that he would not disappoint them. Eventually, though, he expected Mr Trump to pivot.

“That’s the way Donald Trump always is,” the lawyer said. “He plays for the win, but there’s always the moment he . . . sees the writing on the wall.”

Via Financial Times