Donald J. Trump at the Trump Taj Mahal casino in Atlantic City in 1990. People who worked with him before he was elected said they saw several parallels between Mr. Trump the businessman and Mr. Trump the steward of the country’s longest government shutdown.Ángel Franco/The New York Times
Three decades ago, Donald J. Trump waged a public battle with the talk show host Merv Griffin to take control of what would become Mr. Trump’s third Atlantic City casino. Executives at Mr. Trump’s company warned that the casino would siphon revenue from the others. Analysts predicted the associated debt would crush him.
The naysayers would be proved right, but throughout the turmoil Mr. Trump fixated on just one outcome: declaring himself a winner and Mr. Griffin a loser.
As president, Mr. Trump has displayed a similar fixation in his standoff with Congress over leveraging a government shutdown to gain funding for a wall on the Mexican border. As he did during decades in business, Mr. Trump has insulted adversaries, undermined his aides, repeatedly changed course, extolled his primacy as a negotiator and induced chaos.
“He hasn’t changed at all,” said Jack O’Donnell, who ran a casino for Mr. Trump in the 1980s and wrote a book about it. “And it’s only people who have been around him through the years who realize that.”
Mr. Trump briefly seemed to follow a more conventional approach for a president seeking consensus: encouraging his party leaders in Congress to negotiate a deal. Senator Mitch McConnell of Kentucky, the Republican majority leader, shepherded a compromise in December that would have kept the government open and put off negotiations over a wall and other border security measures.
Mr. Trump was expected to sign off on the deal, but then came the suggestion from conservative critics that he had caved in to Democrats — that he was a loser. It was a perception Mr. Trump could not bear, and he quickly reversed course.
He also reverted to lifelong patterns in business. People who worked with him during those years say they see multiple parallels between Mr. Trump the businessman and Mr. Trump the steward of the country’s longest government shutdown.
His lack of public empathy for unpaid federal workers echoes his treatment of some construction workers, contractors and lawyers whom he refused to pay for their work on his real estate projects. The plight of the farmers and small-business owners wilting without the financial support pledged by his administration harks back to the multiple lenders and investors who financed Mr. Trump’s business ventures only to come up shortchanged.
And his ever-changing positions (I’ll own the shutdown; you own the shutdown; the wall could be steel; it must be concrete; then again, it could be steel) have left heads in both parties spinning. Even after his televised proposal on Saturday to break the deadlock, Mr. Trump has no progress to show.
“I think he was always a terrible negotiator,” said Tony Schwartz, co-author with Mr. Trump of “The Art of the Deal.”
That book, published in 1987, was intended to be an autobiography of Mr. Trump, who was 41 at the time. Mr. Schwartz said that he created the idea of Mr. Trump as a great deal maker as a literary device to give the book a unifying theme. He said he came to regret the contribution as he watched Mr. Trump seize on the label to sell himself as something he was not — a solver of complicated problems.
Federal employees and their supporters rallied outside the White House this month. President Trump’s lack of public empathy for unpaid federal workers echoes his treatment of some construction workers, contractors and lawyers whom he refused to pay for their work on his real estate projects.Leigh Vogel for The New York Times
Rather, Mr. Schwartz said, Mr. Trump’s “virtue” in negotiating was his relentlessness and lack of concern for anything but claiming victory.
“If you don’t care what the collateral damage you create is, then you have a potential advantage,” he said. “He used a hammer, deceit, relentlessness and an absence of conscience as a formula for getting what he wanted.”
In a brief telephone interview on Sunday, Mr. Trump was not specific in defending his tactics, but he described himself as successful in his chosen fields of real estate, entertainment and finally politics. “I ran for office once and I won,” Mr. Trump said.
The president’s supporters say he gets an unfair rap as a poor negotiator, saying that his style and unusual approach — and unwillingness to accept defeat even in the worst situations — have often had positive results. And in a Washington that doesn’t like outsiders, he has clearly forced his adversaries out of their comfort zones.
“President Trump’s success in business has translated into success as president,” Sarah Huckabee Sanders, the White House press secretary, said. “He’s ignited a booming economy with rising wages and historically low unemployment, negotiated better trade deals, persuaded our allies to contribute their fair share to NATO, and secured the release of American hostages around the world.”
Representative Peter King, Republican of Long Island, said that even as Mr. Trump’s personal popularity had taken a hit during the shutdown, public support for his stated ambition — the border wall — had grown.
“Having the bad hand that he dealt himself at the beginning, I think he’s making the best of it, better than anybody else could,” Mr. King said. “Only he would have the stamina, the determination to just keep going.”
One example of that stamina — seen by others as evidence of unreliability — recounted in Mr. O’Donnell’s book, “Trumped! The Inside Story of the Real Donald Trump — His Cunning Rise and Spectacular Fall,” written with James Rutherford, involved the construction of an exclusive lounge at the top of a casino.
Mr. Trump liked very high ceilings, according to the account. He screamed and cursed when he was told some ceilings had to be low to allow for pipes. He begrudgingly acquiesced. But he had forgotten by the time he next visited the construction site. He cursed again. Was reminded again. To the bewilderment of his executives, that cycle repeated itself several times.
Finally, toward the end of construction, Mr. Trump reamed an executive with vulgarities, leapt up and punched a hole in one of the low ceilings. “After that day,” Mr. O’Donnell wrote, “Donald never set foot inside it again if he could help it.”
In recent weeks, Mr. Trump has similarly laced into his acting chief of staff, Mick Mulvaney.
Mr. Mulvaney pursued a rather standard tactic in ending the impasse over border security and a wall: He tried to find middle ground between the $1.3 billion to which Democrats had once agreed, and the president’s demand for $5.7 billion. But upon learning of Mr. Mulvaney’s efforts, Mr. Trump snarled in front of a crowded room that Mr. Mulvaney had messed “it all up” (using a vulgarity, according to two White House officials familiar with the remark.)
Ivana Trump in front of the Plaza Hotel in 1987. Jared Kushner, right, at the White House last year.Joe McNally/Getty Images; Doug Mills/The New York Times
“We are getting crushed!” Mr. Trump told Mr. Mulvaney, after watching television coverage of the shutdown.
During his years in business, Mr. Trump earned a reputation as someone whose word meant very little. When a commitment he made no longer made sense, he walked away, often blaming the other party with a fantastical line of reasoning.
To win financing from Deutsche Bank to build a Trump Hotel in Chicago, for example, Mr. Trump personally guaranteed $40 million of the debt. When he could not make his payments during the 2008 financial crisis, Deutsche Bank executives were open to granting him more time to repay the loan, a person briefed on negotiations later recalled.
But before a compromise could be reached, Mr. Trump flipped the script. He filed a lawsuit and argued that the bank had helped cause the worldwide financial meltdown that essentially rendered Mr. Trump unable to make his debt payments. At the time, Deutsche Bank called the lawsuit “classic Trump.”
The bank eventually settled with Mr. Trump, saving him from having to pay the $40 million. Mr. Trump expressed his gratitude to the lawyer who fought on his behalf by not fully paying his bill. “He left me with some costs,” said the lawyer, Steven Schlesinger.
From the time he built his first Manhattan apartment building, Mr. Trump left a string of unpaid tabs for the people who worked for him.
The undocumented Polish workers who did the demolition work for that first building, Trump Tower, eventually won a $1.375 million settlement. Since then, scores of lawyers, contractors, engineers and waiters have sued Mr. Trump for unpaid bills or pay. Typically, he responds by asserting that their work did not meet his standard.
That might sound familiar to furloughed federal workers. Mr. Trump recently retweeted an article, attributed to an anonymous senior official in his administration, arguing that 80 percent of federal workers do “nothing of external value” and that “furloughed employees should find other work, never return and not be paid.”
Mr. Trump has claimed, without evidence, that “maybe most” federal workers going without pay are “the biggest fan” of his use of the shutdown to fund a border wall. In ordering thousands back to work without pay, he has put the pain for the shutdown on them.
Mr. Trump has also embraced his business practice of giving the most latitude and trust to family members, no matter their prior experience.
He put his first wife, Ivana, a model, in charge of an Atlantic City casino and the Plaza Hotel in Manhattan. He put his younger brother, Robert, who had some background in corporate finance, in senior positions at the casinos. Not long after three of his children graduated from college, he vested authority in them over golf courses, hotels and licensing deals.
Merv Griffin during the taping of his final show in Los Angeles in 1986. Speaker Nancy Pelosi, right, appearing on a television screen in the Capitol this month.Doug Pizac/Associated Press; Pete Marovich for The New York Times
In the White House, Mr. Trump has increasingly leaned on his son-in-law, Jared Kushner, for guidance on dealing with Congress amid the current stalemate. Mr. Kushner, who like Mr. Trump is the son of a wealthy real estate developer, has not always impressed old hands on Capitol Hill.
He began some early conversations by saying that Democrats would need to yield because his father-in-law would not budge, a statement that lawmakers found naïve, according to Democrats familiar with the remarks.
With Democrats now in charge of the House of Representatives, Mr. Trump also has a new set of adversaries, and other old habits from his years in business have re-emerged.
Through his Twitter feed, he has verbally pummeled Senator Chuck Schumer, the minority leader, and tried to drive a wedge between Mr. Schumer and his fellow Democrat, Speaker Nancy Pelosi.
Barbara Res, who said she enjoyed much about working for Mr. Trump as a construction executive in the 1980s and 1990s, sees in Ms. Pelosi a new challenge to Mr. Trump’s lifelong tactics. One blind spot she observed was that Mr. Trump “believes he’s better than anyone who ever lived” and saw even the most capable of women as easy to run over.
“But there was never a woman with power that he ran up against, until Pelosi,” she said. “And he doesn’t know what to do with it. He’s totally in a corner.”
In the interview, Mr. Trump described Ms. Res, Mr. O’Donnell and Mr. Schwartz as disgruntled workers whom he had shunted aside, who had experience with him for relatively brief periods and who were simply using his name for attention.
During his years in business, Mr. Trump rarely displayed an interest in details or expert opinions that might have informed whether his plans would actually work. That pattern has also emerged in the shutdown dispute.
Thirty years ago, his claimed defeat of Mr. Griffin turned out to be a Pyrrhic victory.
Within months of completing construction on his third casino, the Trump Taj Mahal, he could not pay interest to the bondholders who had financed the project. Having overpaid and overleveraged himself on other deals, banks forced him to turnover or sell almost everything.
His wealthy father helped bail him out. But Mr. Trump blamed everyone else. He fired nearly all his top executives and stopped paying contractors who had built the casino.
In describing the border wall, Mr. Trump has expressed unending confidence in its efficacy. Others, including Representative Will Hurd, a Republican whose Texas district includes part of the border with Mexico, have described it as a tall speed bump, nearly useless without technology to spot illegal crossings immediately and dispatch border agents to quickly respond.
Mr. O’Donnell, the casino manager, said long-term consequences never concerned Mr. Trump. He was always willing to pay too much in order to get a deal signed so he could declare victory, he said.
“He just wants to get the deal,” Mr. O’Donnell said.
Ben Protess and Steve Eder contributed reporting.