Trump Lost Over $1 Billion in 10 Years: A Closer Look

-He used a fake name to call a reporter
and brag about how much his father loves him.
Man, I would say the dude needs to therapy,
but I don’t think he can afford it.
.. Maybe he can just use a fake name and be his own therapist.
“And how does that make you feel, Donald?”
“I feel smart, Dr. Barron.” [ Laughter ]
“You are smart, Donald. That’ll be $200.”
“Uh…” [ Laughter ]
“Can I owe you?”
.. Trump was never a successful businessman.

He just played one on TV.
Expecting Donald Trump to exhibit business acumen
is like expecting George Clooney to do an arterial bypass.
We already knew he was a con artist.
It’s also a story about the thing
Trump cynically claimed to fix,
the thing he actually benefited from his entire life,
the rigged system.
Most regular people are one layoff
or medical emergency away from a financial crisis,
but this guy lost a billion dollars over 10 years
and he ended up fine —
except for the fact that he went from looking
like the wolf of Wall Street
to a guy getting chased by a pack of wolves.

In Business and Governing, Trump Seeks Victory in Chaos

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 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.

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.

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.”

.. 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.

.. 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.

.. 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.

Have You Ever Seen Donald Trump Laugh?

As Trump himself might say, there’s something going on.

The less honest you are with yourself, the less likely you are to laugh.

.. “Self-deception inhibits laughter.”

.. “There’s a huge correlation showing that people who score high in self-deception laugh less,” Lynch told me. Furthermore, he said, “there’s a pretty robust correlation between self-deception and an inflated ego, or unwarranted high self-esteem. Some of the self-deception is telling yourself that you’re greater, more powerful, smarter than you are.”

.. It’s a lot harder to laugh when you don’t recognize absurdity. Think of how much Trump must have had to lie to himself, perhaps even unconsciously, in order to convince millions that Obama was born in Kenya
.. (By the way, the liars-laugh-less formulation doesn’t work in reverse: People who don’t laugh aren’t necessarily self-deceptive or narcissistic at all.
.. some people don’t laugh out of low self-esteem. “Self-deception,” Lynch estimates, “explains about 20 percent of why people don’t laugh.” Besides, if we didn’t tell ourselves little white lies, he adds, “we wouldn’t get out of the bed in the morning.”)
.. “Superficially, the problem that torments Trump is trade. But his language—they ‘beat’ us and ‘laugh’ at us—provokes the emotional power of shame,”
..  “all about shame—avoiding it himself, and inflicting it on others.”
..  As his biographer, I see it in his struggle to satisfy a strict and demanding father and his banishment, at age 13, to a military academy in Upstate New York where, Trump has said, he was subject to violence at the hands of Army veterans who staffed the school.
.. Trump was major-shamed again, D’Antonio writes, “when he lost his Trump Airline and the Plaza Hotel and became a symbol of failure in the late 1980s and early 1990s. Out of this defeat he fashioned a comeback that saw him become richer and more famous than ever.”
.. At the 2011 White House Correspondents Dinner, for example, President Obama coolly humiliated the birther-in-chief, getting the crowd and soon the whole world to laugh at him, while Trump sat there stone-faced. In all likelihood, that experience motivated him to finally make a real run for the presidency.
.. As best we can tell, Trump’s whole psychological dynamic might be explained as a serial encounter with public shame over his fear of inadequacy.
.. Like Dostoevsky’s The Gambler, Trump likes the thrill of getting so close to being exposed and still winning—until, of course, he finally loses, which may be what he really wants
.. “laughter relieves shame.” Laughing, especially at oneself, “is one of the main ways in which shame can be dissipated or released.”