At Deutsche Bank, Mr. Offit’s mandate was to lend money to big real estate developers, package the loans into securities and sell the resulting bonds to investors. He said in an interview that one way to stand out in a crowded market was to make loans that his rivals considered too risky.
In 1998, a broker contacted him to see if he would consider lending to a Wall Street pariah: Mr. Trump, who was then a casino magnate whose bankruptcies had cost banks hundreds of millions of dollars.
Mr. Offit took the meeting.
A few days later, Mr. Offit’s secretary called him. “Donald Trump is in the conference room,” she whispered. Mr. Offit said he rushed in, expecting to find an entourage. Mr. Trump was alone.
He was looking for a $125 million loan to pay for gut renovations of 40 Wall Street, his Art Deco tower in Lower Manhattan. Mr. Offit was impressed by the pitch, and the loan sailed through Deutsche Bank’s approval process.
Mr. Trump seemed giddy with gratitude, Mr. Offit recalled. He took Mr. Offit golfing. He flew him by helicopter to Atlantic City for boxing matches. He wrote a grateful note to Sidney Offit for having “a great son!”
Mr. Offit commissioned a detailed model of 40 Wall Street. A golden plaque on its pedestal bore the names and logos of Deutsche Bank and the Trump Organization. Mr. Offit gave one to Mr. Trump and kept another in his office.
Mr. Trump soon came looking for $300 million for the construction of a skyscraper across from the United Nations headquarters. The loan was approved. He wanted hundreds of millions more for his Trump Marina casino in Atlantic City. Mr. Offit pledged to line up cash for that, too.
Not long after, Edson Mitchell, a top bank executive, discovered that the signature of the credit officer who had approved the Trump Marina deal had been forged, Mr. Offit said. (Mr. Offit was never accused of forgery; the loan never went through.)
Mr. Offit was fired months later. He said it was because Mr. Mitchell claimed that he was reckless, a charge Mr. Offit disputed.
It was the first hiccup in the Trump relationship. It would not be the last.
Over the next few years, the commercial real estate group, with Mr. Kennedy now in a senior role, kept lending to Mr. Trump, including to buy the General Motors building in Manhattan. Occasionally, Justice Kennedy stopped by Deutsche Bank’s offices to say hello to the team, executives recalled.
At an annual pro-am golf tournament the bank hosted outside Boston in the early 2000s, Mr. Trump sat down for a recorded interview with the bank’s public relations staff, who asked about his experience with Deutsche Bank.
“It’s great,” Mr. Trump exclaimed, according to a person who witnessed the interview. “They’re really fast!”
In 2003, a Deutsche Bank team led by Richard Byrne — a former casino-industry analyst who had known Mr. Trump since the 1980s — was hired to sell bonds on behalf of Trump Hotels & Casino Resorts. Bank officials escorted Mr. Trump to meet institutional investors in New York and Boston, according to an executive who attended.
The so-called roadshow seemed to go well. At every stop, Mr. Trump was greeted by large audiences of fund managers, executives and lower-level employees eager to see the famous mogul. The problem, as a Deutsche Bank executive would explain to Mr. Trump, was that few of them were willing to entrust money to him.
Mr. Trump requested an audience with the bank’s bond salesmen.
According to a Deutsche Bank executive who heard the remarks, Mr. Trump gave a pep talk. “Fellas, I know this isn’t the easiest thing you’ve had to sell,” the executive recalled Mr. Trump saying. “But if you get this done, you’ll all be my guests at Mar-a-Lago,” his private club in Palm Beach, Fla.
The sales team managed to sell hundreds of millions of dollars worth of bonds. Mr. Trump was pleased with the results when a Deutsche Bank executive called, according to a person who heard the conversation.
“Don’t forget what you promised our guys,” the executive reminded him.
Mr. Trump said he did not remember and that he doubted the salesmen actually expected to be taken to Mar-a-Lago.
“That’s all they’ve talked about the past week,” the executive replied.
Mr. Trump ultimately flew about 15 salesmen to Florida on his Boeing 727. They spent a weekend golfing with Mr. Trump, two participants said.
A year later, in 2004, Trump Hotels & Casino Resorts defaulted on the bonds. Deutsche Bank’s clients suffered steep losses. This arm of the investment-banking division stopped doing business with Mr. Trump.
.. Mr. Trump told Deutsche Bank his net worth was about $3 billion, but when bank employees reviewed his finances, they concluded he was worth about $788 million, according to documents produced during a lawsuit Mr. Trump brought against the former New York Times journalist Timothy O’Brien. And a senior investment-banking executive said in an interview that he and others cautioned that Mr. Trump should be avoided because he had worked with people in the construction industry connected to organized crime.
Nonetheless, Deutsche Bank agreed in 2005 to lend Mr. Trump more than $500 million for the project. He personally guaranteed $40 million of it, meaning the bank could come after his personal assets if he defaulted.
By 2008, the riverside skyscraper, one of the tallest in America, was mostly built. But with the economy sagging, Mr. Trump struggled to sell hundreds of condominium units. The bulk of the loan was due that November.
Then the financial crisis hit, and Mr. Trump’s lawyers sensed an opportunity.
A provision in the loan let Mr. Trump partially off the hook in the event of a “force majeure,” essentially an act of God, like a natural disaster. The former Federal Reserve chairman Alan Greenspan had called the financial crisis a tsunami. And what was a tsunami if not a natural disaster?
.. One of Mr. Trump’s lawyers, Steven Schlesinger, told him the provision could be used against Deutsche Bank.
“It’s brilliant!” Mr. Schlesinger recalled Mr. Trump responding.
Days before the loan was due, Mr. Trump sued Deutsche Bank, citing the force majeure language and seeking $3 billion in damages. Deutsche Bank countersued and demanded payment of the $40 million that Mr. Trump had personally guaranteed.
With the suits in court, senior investment-banking executives severed ties with Mr. Trump.
.. Ms. Vrablic’s superiors encouraged her to make loans that rival banks dismissed as too large or complex. They saw it as a way to elbow into the hypercompetitive New York market.
.. One of Ms. Vrablic’s clients was Jared Kushner, who married Ivanka Trump in 2009. Mr. Kushner regarded Ms. Vrablic as the best banker he had ever worked with, according to a person familiar with his thinking.
Shortly after the Chicago lawsuit was settled, Mr. Kushner was told that Mr. Trump was looking for a loan and introduced him to Ms. Vrablic, according to people familiar with the relationship.
.. Mr. Trump flew Ms. Vrablic to Miami to show her a property he wanted to buy: the Doral Golf Resort and Spa. He needed more than $100 million for the 72-hole property.
Deutsche Bank dispatched a team to Trump Tower to inspect Mr. Trump’s personal and corporate financial records. The bankers determined he was overvaluing some of his real estate assets by as much as 70 percent, according to two former executives.
.. By then, though, Mr. Trump had become a reality-TV star, and he was swimming in cash from “The Apprentice.” Deutsche Bank officials also were impressed that Mr. Trump did not have much debt, according to people who reviewed his finances. Aside from his history of defaults, he was an attractive borrower.
Mr. Trump also expressed interest in another loan from the private-banking division: $48 million for the same Chicago property that had provoked the two-year court fight.
Mr. Trump told the bank he would use that loan to repay what he still owed the investment-banking division, the two former executives said. Even by Wall Street standards, borrowing money from one part of a bank to pay off a loan from another was an extraordinary act of financial chutzpah.
.. Investment-banking executives, including Anshu Jain, who would soon become Deutsche Bank’s co-chief executive, pushed back. Lending to Mr. Trump again would be foolish, they argued, and signal to clients that they could default and even sue the bank.
Executives in the private bank countered that the proposed loans had Mr. Trump’s personal guarantee and therefore were low risk. And the Chicago loan, they noted, would lead to the repayment of tens of millions of dollars that Mr. Trump still owed the investment-banking division.
A top executive with responsibility for the private bank discussed the loans with Mr. Ackermann, the chief executive, who supported them, according to two officials. A powerful committee in Frankfurt, which evaluated loans based on risks to the bank’s reputation, signed off.
“There is no objection from the bank to proceed with this client,” wrote Stuart Clarke, the chief operating officer for the Americas, in a Dec. 5, 2011, email, according to a recipient.
Deutsche Bank wired the money to Mr. Trump. The loans carried relatively low interest rates, executives said, but the business promised to be profitable: As part of the deal, Mr. Trump would hold millions of dollars in a personal account, generating fees for the bank.
“I have no recollection of having been asked to approve that private-banking loan,” Mr. Ackermann said in an interview. He added: “I would have approved it, if it came to me, if it was commercially sound.”
Ms. Vrablic’s relationship with the Trumps deepened.
Deutsche Bank lent money to Donald Trump Jr. for a South Carolina manufacturing venture that would soon go bankrupt. It provided a $15 million credit line to Mr. Kushner and his mother, according to financial documents reviewed by The Times. The bank previously had an informal ban on business with the Kushners because Jared’s father, Charles, was a felon.
In 2012, Jared Kushner recommended that the editor of The Mortgage Observer, one of the publications he owned, write a profile of Ms. Vrablic. The editor, Carl Gaines, knew Mr. Kushner was her client and objected, according to a person familiar with the exchange.
“Just go meet with her,” Mr. Kushner said. “You’ll figure something out.”
A gauzy profile of Ms. Vrablic was published in February 2013.
Shortly afterward, the private bank produced a promotional video featuring some of its marquee clients. The video was played at a retreat for Deutsche Bank’s senior leadership in Barcelona. In it, Ivanka Trump extolled the private bank’s work with her family and thanked their relationship manager, according to two people who saw the video.
.. In early 2014, Mr. Trump and his personal lawyer, Michael Cohen, approached Ms. Vrablic about more potential loans.
The owner of the Buffalo Bills had died, and the N.F.L. franchise was up for sale. Mr. Trump was interested, and he needed to show the league he had the financial wherewithal to pull off a transaction that could top $1 billion.
Mr. Trump asked Ms. Vrablic if the bank would be willing to make a loan and handed over bare-bones financial statements that estimated his net worth at $8.7 billion.
.. Mr. Cohen testified to Congress last month that the documents exaggerated Mr. Trump’s wealth. Deutsche Bank executives had reached a similar conclusion. They nonetheless agreed to vouch for Mr. Trump’s bid, according to an executive involved.
Mr. Trump’s bid did not win, but another lending opportunity soon arose.
A federal agency had selected Mr. Trump to transform the Old Post Office Building in Washington into a luxury hotel. But his financial partner — the private equity firm Colony Capital, run by Thomas J. Barrack Jr. — pulled out. Mr. Trump needed nearly $200 million.
.. Because of his decades-long pattern of defaults and his increasingly polarizing political rhetoric — among other things, he had been spreading a lie about President Barack Obama being born overseas — Mr. Trump remained untouchable for most banks.
Ms. Vrablic was willing to help.
In a memo outlining the rationale for the Old Post Office loan, Ms. Vrablic said Mr. Trump was expected to add large sums to his brokerage account if he received the loan, according to an executive who read the document.
This time, there was less internal opposition. One reason: Mr. Jain — by then the bank’s co-chief executive — had a solid relationship with Ms. Vrablic. Mr. Jain accompanied her to meetings with high-profile clients, and he praised her work to colleagues, multiple executives said.
..On a foggy Wednesday in February 2013, Ms. Vrablic and Mr. Jain went to Trump Tower to meet with Mr. Trump, according to two executives with knowledge of the meeting. Ms. Vrablic’s rapport with the client was immediately clear: Mr. Trump’s assistant greeted her as an old friend, and she seemed relaxed with Mr. Trump and his daughter, one executive said.
.. They discussed Mr. Trump’s finances over lunch, and Mr. Jain said he was surprised by his low level of debt, the executives said. After lunch, Ms. Vrablic told her colleagues that Mr. Jain had sounded upbeat about Mr. Trump’s finances.
A $170 million loan to pay for the overhaul of the Old Post Office went through in 2015, and Mr. Trump added more money to his brokerage account. (In May 2016, he reported up to $46 million of stocks and bonds in the account.)
.. On Aug. 6, 2015, Mr. Trump participated in the first Republican presidential debate. He clashed with the Fox News moderator, Megyn Kelly. He flew back to New York early the next morning. That evening, he called in to a CNN talk show and said of Ms. Kelly that there was “blood coming out of her wherever.”
In the intervening hours, Mr. Trump had used a black Sharpie to sign documents for another loan from Deutsche Bank: $19 million for the Doral resort. That brought to more than $300 million the total lent under Ms. Vrablic.
.. On the campaign trail, rivals assailed Mr. Trump’s financial history. In response, he pointed to Deutsche Bank-funded successes like the Old Post Office project, now a gleaming hotel a few blocks from the White House.
.. In early 2016, Mr. Trump asked Ms. Vrablic for one final loan, for his golf course in Turnberry, Scotland.
.. Ms. Vrablic said yes, but a fight soon erupted.
Jacques Brand, who was in charge of Deutsche Bank’s American businesses, angrily objected, partly because of Mr. Trump’s divisive rhetoric.
Ms. Vrablic appealed the decision. Senior executives in Frankfurt, including Christian Sewing, who would become chief executive in 2018, were shocked that the private bank would consider lending Mr. Trump money during the campaign, bank officials said.
The bank’s reputational risk committee killed the transaction in March 2016.
.. That same month, as The Times was preparing an article about Mr. Trump’s excommunication from Wall Street, he cited his warm relationship with Deutsche Bank.
.. “They are totally happy with me,” he said to The Times. “Why don’t you call the head of Deutsche Bank? Her name is Rosemary Vrablic. She is the boss.”
.. After Mr. Trump won the election, Deutsche Bank’s board of directors rushed to understand how the bank had become the biggest lender to the president-elect.
A report prepared by the board’s integrity committee concluded that executives in the private-banking division were so determined to win business from big-name clients that they had ignored Mr. Trump’s reputation for demagogy and defaults, according to a person who read the report.
The review also found that Deutsche Bank had produced a number of “exposure reports” that flagged the growing business with Mr. Trump, but that they had not been adequately reviewed by senior executives.
.. On Deutsche Bank’s trading floor, managers began warning employees not to use the word “Trump” in communications with people outside the bank. Salesmen who violated the edict were scolded by compliance officers who said the bank feared stoking public interest in its ties to the new president.
One reason: If Mr. Trump were to default on his loans, Deutsche Bank would have to choose between seizing his assets or cutting him a lucrative break — a situation the bank would rather resolve in private.
.. Two years after Mr. Trump was sworn in, Democrats took control of the House of Representatives. The chamber’s financial services and intelligence committees opened investigations into Deutsche Bank’s relationship with Mr. Trump. Those inquiries, as well as the New York attorney general’s investigation, come at a perilous time for Deutsche Bank, which is negotiating to merge with another large German lender.
Next month, Deutsche Bank is likely to start handing over extensive internal documents and communications about Mr. Trump to the congressional committees, according to people briefed on the process.
Ms. Vrablic, who is intensely private and rarely discusses her personal life with colleagues, declined to comment. People familiar with her thinking said she expected to be called to testify publicly on Capitol Hill.
Doug Heller, the executive director of Consumer Watchdog, said Trump is the “most egregious, almost comical example” of the disparity between what the average American faces when going through bankruptcy and the “ease with which the very rich can move in and out of bankruptcy.”
.. “Under the American bankruptcy laws, if you end up in bankruptcy because you’re struggling with divorce or medical payments or a sudden change of income, it’s a disaster. If you fail miserably with huge dollars involved then you just need some accountants to rework your books,” Heller said.
.. “There’s that old saying, ‘If you owe your banks a little, you’re at their mercy. If you owe the banks a lot, the banks are at your mercy. They saw the best way for him to repay the money was to keep the Donald afloat.”
.. Donald struck a deal with the banks to hand over half his ownership, and half of the equity, in the casino in exchange for a lower interest rate and more time to pay off his debt. He sold off his beloved Trump Princess yacht and the Trump Shuttle airplane to make his payments, and his creditors put him on a budget, putting a cap on his personal spending.
.. He also had the humiliation of having some bankers deciding how much money he could spend — the numbers are just astonishing — the amount of his monthly budget,” LoPucki said.
.. banks would often agree to lose millions in reorganizations like Trump’s to prevent the massive losses they would incur if they foreclosed on the property.
“Banks will take considerable haircuts,” Pottow said. “It’s sort of like you have a sick patient so you cut off a couple toes to stop the gangrene. Now he’s missing a few toes, but he’s still alive.”
.. “Here’s a guy who’s failed so miserably so many times and it’s not as though he had to claw his way back after seven years in credit hell. He just said. ‘OK, this isn’t my problem anymore.’ For him, it’s just been a platform to the next money-making scheme,”
.. In 2004 Trump Hotels and Casino Resorts Inc. filed for voluntary bankruptcy after accumulating $1.8 billion in debt.
.. “In 2004 is where he lost control of his name. One rule when you have a name like Trump is you never let anyone own it and control it. He got into such a bad spot here that he ended up with others owning and controlling his name. They can do what they want once they own it,” LoPucki said.
.. Shortly after the proceedings, Trump told CNN’s Geri Willis that his personal fortune would not be affected. “This is a very small portion of my net worth. It’s less than 2 percent,” he said.
.. in 2008, so too did Trump’s real estate holdings. Trump Entertainment and his affiliated companies had $2.06 billion in assets and was $1.74 billion in debt.
.. LoPucki said it was very unusual for anyone to have that many large businesses go through bankruptcy. Most of the debt Trump incurred was through bonds that were sold to the public.
“People knew who Donald Trump was and for that reason were willing to trust the bonds, and they got burned,” LoPucki said. “The people who invested with him or based on his name lost money, but he himself came out pretty well.“
He’s long-boasted of how his business acumen makes him fit for president. But, Kurt Eichenwald delves into the history of his deals and finds a catalogue of calamitous ventures
The year was 1993, and his target was Native Americans, particularly those running casinos who, Trump was telling a congressional hearing, were sucking up to criminals.
Trump, who at the time was a major casino operator, appeared before a panel on Native American gaming with a prepared statement that was level-headed and raised regulatory concerns in a mature way. But, in his opening words, Trump announced that his written speech was boring, so he went off-script, even questioning the heritage of some Native American casino operators, saying they “don’t look like Indians” and launching into a tirade about “rampant” criminal activities on reservations.
.. His words were, as is so often the case, incendiary. Lawmakers, latching onto his claim to know more than law enforcement about ongoing criminal activity at Native American casinos, challenged Trump to bring his information to the FBI. One attacked Trump’s argument as the most “irresponsible testimony” he had ever heard.
.. For opponents of Trump’s presidential run, this contretemps about Native Americans might seem like a distant but familiar echo of the racism charges that have dogged his campaign, including his repeated taunting of Senator Elizabeth Warren as “Pocahontas” because she claims native ancestry.
.. Trump, through his offensive tantrum, was throwing away financial opportunities, yet another reminder that, for all his boasting of his acumen and flaunting of his wealth, the self-proclaimed billionaire has often been a lousy businessman.
.. As Trump was denigrating Native Americans before Congress, other casino magnates were striking management agreements with them.
.. in his purposeless, false and inflammatory statements before Congress, Trump alienated politicians from around the country, including some who had the power to influence construction contracts –problems that could have been avoided if he had simply read his prepared speech rather than ad-libbing.
.. Lost contracts, bankruptcies, defaults, deceptions and indifference to investors – Trump’s business career is a long, long list of such troubles
.. arrogance and recklessness of a businessman whose main talent is self-promotion... He is also pretty good at self-deception, and plain old deception... “I’m just telling you, you wouldn’t say that you’re failing,” he said in a 2007 deposition when asked to explain why he would give an upbeat assessment of his business even if it was in trouble. “If somebody said, ‘How you doing?’ You’re going to say you’re doing good.” Perhaps such dissembling is fine in polite cocktail party conversation, but in the business world it’s called lying... And while Trump is quick to boast that his purported billions prove his business acumen, his net worth is almost unknowable given the loose standards and numerous outright misrepresentations he has made over the years. In that 2007 deposition, Trump said he based estimates of his net worth at times on “psychology” and “my own feelings”. But those feelings are often wrong – in 2004, he presented unaudited financials to Deutsche Bank while seeking a loan, claiming he was worth $3.5bn. The bank concluded Trump was, to say the least, puffing; it put his net worth at $788m, records show.
.. He personally guaranteed $40m of the loan to his company, so Deutsche coughed up. He later defaulted on that commitment.
.. Trump’s many misrepresentations of his successes and his failures matter – a lot.
.. He has no voting record and presents few details about specific policies. Instead, he sells himself as qualified to run the country because he is a businessman who knows how to get things done, and his financial dealings are the only part of his background available to assess his competence to lead the country. And while Trump has had a few successes in business, most of his ventures have been disasters.
.. When he was ready for college, Trump wanted to be a movie producer, perhaps the first sign that he was far more interested in the glitz of business than the nuts and bolts.
.. He applied to the University of Southern California to pursue a film career, but when that didn’t work out, he attended Fordham University; two years later, he transferred to the Wharton School of Business at the University of Pennsylvania and got a degree in economics.
.. Almost all of his best-known successes are attributable to family ties or money given to him by his father.
.. The son of wealthy developer Fred Trump, he went to work for his father’s real estate business immediately after graduating from Wharton and found some success by taking advantage of his father’s riches and close ties to the power brokers in the New York Democratic Party, particularly his decades-long friend Abe Beame, the former mayor of the city.
Even with those advantages, a few of Trump’s initial deals for his father were busts, based on the profits.
His first project was revitalising the Swifton Village apartment complex in Cleveland, which his father had purchased for $5.7m in 1962. After Trump finished his work, they sold the complex for $6.75m, which, while appearing to be a small return, was a loss; in constant dollars, the apartment buildings would have had to sell for $7.9m to have earned an actual profit. Still, Trump happily boasted about his supposed success with Swifton Village and about his surging personal wealth.
.. in 1970, he took another shot at joining the entertainment business by investing $70,000, to snag a co-producer’s credit for a Broadway comedy called Paris Is Out! Once again, Trump failed; the play bombed, closing after just 96 performances.
.. The next year, he moved to Manhattan from the outer boroughs, still largely dependent on Daddy. In 1972, Trump’s father brought him into a limited partnership that developed and owned a senior citizen apartment complex in East Orange, New Jersey.
Fred Trump owned 75 per cent, but two years later shrunk his ownership to 27 per cent by turning over the rest of his stake to two entities controlled by his son. Another two years passed, and then Fred Trump named him the beneficiary of a $1m trust that provided him with $1.3m in income (2015 dollars) over the next five years.
.. In 1978, he boosted his son’s fortunes again, hiring him as a consultant to help sell his ownership interest in a real estate partnership to the Grandcor Company and Port Electric Supply Corp. The deal was enormously lucrative for Donald Trump, particularly since it just fell into his lap thanks to his family. Under the deal, Grandcor agreed to pay him an additional $190,000, while Port Electric kicked in $228,500. The payments were made over several years, but the value in present-day dollars on the final sum he received is $10.4m.
.. Despite having no real success of his own, by the late 1970s, Trump was swaggering through Manhattan, gaining a reputation as a crass self-promoter. He hung out in the fancy nightspot Le Club, where he was chums with prominent New Yorkers like Roy Cohn, the one-time aide to Senator Joe McCarthy who was one of the city’s most feared and politically connected attorneys. Cohn became one of the developer’s lifelong mentors, encouraging the pugilistic personality that showed itself all the way back in second grade, when Trump punched his music teacher.
.. Soon Trump gained the public recognition he craved. Through a wholly owned corporation called Wembley Realty, Trump struck a partnership with a subsidiary of Hyatt Hotels. That partnership, Regency Lexington, purchased the struggling Commodore Hotel for redevelopment into the Grand Hyatt New York, a deal Trump crowed about when he announced he was running for president.He failed to mention that this deal was once again largely attributable to Daddy, who co-guaranteed with Hyatt a construction loan for $70m and arranged a credit line for his boy with Chase Manhattan Bank.
.. The credit line was a favour to the Trump family, which had brought huge profits to the bank; according to regulatory records, the revolving loan was set up without even requiring a written agreement. Topping off the freebies and special deals that flowed Trump’s way, the city tossed in a 40-year tax abatement. Trump’s “success” with the Hyatt was simply the result of money from his dad, his dad’s bank, Hyatt and the taxpayers of New York City.
.. Despite the outward signs of success, Trump’s personal finances were a disaster. In 1978, the year his father set up that sweet credit line at Chase, Donald’s tax returns showed personal losses of $406,386 – $1.5m in present-day dollars. Things grew worse in 1979, when he reported an income of negative $3.4m, $11.2m in constant dollars. All of this traced back to big losses in three real estate partnerships and interest he owed Chase. With Trump sucking wind and rapidly drawing down his line of credit, he turned again to Daddy, who in 1980 agreed to lend him $7.5m.
.. All of these names and numbers can grow confusing for voters with little exposure to the business world. So to sum it all up, Trump is rich because he was born rich – and without his father repeatedly bailing him out, he would have likely filed for personal bankruptcy before he was 35. As his personal finances were falling apart, Trump got a big idea for how to make money: casinos... At the time, Trump was deep into plans to turn Bonwit Teller’s flagship department store into Trump Tower – a transformation achieved with the help of Roy Cohn, who fought in the courts to win Trump a huge tax abatement. Still, Trump jumped on the casino idea and had a lawyer reach out to the owners to negotiate a lease deal... Trump wanted to build a 39-story, 612-room hotel and casino, but the banks refused to finance his adventure. So, instead, he struck a partnership with Harrah’s Entertainment in which the global gaming company and subsidiary of Holiday Inn Inc put up all the money in exchange for Trump developing the property. In 1984, Harrah’s at Trump Plaza opened, and Trump seethed. He had wanted his name to be the marquee brand, even though Harrah’s had an international reputation in casinos and he had none. He even delayed building a garage because his name was not being used prominently enough in the marketing.
..According to court papers, Harrah’s spent $9.3m promoting the Trump name, giving the New York developer a reputation in the casino business he’d never had before. And Harrah’s quickly learned the price – now, with Trump able to argue he knew casinos, financing opportunities that did not exist before opened up, and he was able to use Harrah’s promotion of him as a lever against the entertainment company. Soon after that first casino opened, Trump took advantage of his new credibility with financial backers interested in the gaming business to purchase the nearly completed Hilton Atlantic City Hotel for just $320m; he renamed it Trump Castle. The business plan was ludicrous: Trump had not only doubled down his bet on Atlantic City casinos but was now operating two businesses in direct competition with each other. When Trump Castle opened in 1985, Harrah’s decided to ditch Trump and sold its interest in their joint venture to him for $220m... Still, he wanted more in Atlantic City – specifically, the Taj Mahal, the largest casino complex ever, which Resorts International was building. This made the Casino Control Commission nervous because it could have meant that the financial security of Atlantic City would be riding on the back of one man.
.. his argument went, he was Donald Trump. He would contain costs, he said, because banks would be practically throwing money at him, and at prime rates. He would be on a solid financial foundation because the banks loved him so much, unlike lots of other companies and casinos that used below-investment-grade, high-interest junk bonds for their financing. “I’m talking about banking institutions, not these junk bonds, which are ridiculous,” he testified... But Trump’s braggadocio proved empty. No financial institution gave him anything. Instead, he financed the deal with $675m in junk bonds, agreeing to pay an astonishing 14 percent interest, about 50 percent more than he had projected.
That pushed Trump’s total debt for his three casinos to $1.2bn. For the renamed Trump Taj Mahal to break even, it would have to pull in as much as $1.3m a day in revenue, more than any casino ever.
Disaster hit fast. As had been predicted by some Wall Street analysts, Trump’s voracious appetite cannibalised his other casinos – it was as if Trump had tipped the Atlantic City boardwalk and slid all his customers at the Trump Castle and Trump Plaza down to the Taj. Revenues for the two smaller casinos plummeted a combined $58m that first year... Trump introduced the airline with his usual style – by insulting the competition. At an elegant event at Logan Airport in Boston, Trump took the stage and suggested that the other airline with a northeastern shuttle, Pan Am, flew unsafe planes. Pan Am didn’t have enough cash, he said, and so it couldn’t spend as much as the Trump Shuttle on maintenance. “I’m not criticising Pan Am,” Trump told the assembled crowd. “I’m just speaking facts.” But Trump offered no proof, and others in the airline industry seethed; talking about possible crashes was bad for everyone’s business.
.. He was spending $1m to update each of the planes, which were individually worth only $4m. With those changes, he boasted, he would increase the shuttle’s market share from 55 to 75 percent. But just like with casinos, Trump was in a business he knew nothing about.
.. Customers on a one-hour flight from Washington to New York didn’t want luxury; they wanted reliability and competitive prices. Trump Shuttle never turned a profit. But it didn’t have much of a chance; even as he was preening about his successes, Trump’s businesses were falling apart and would soon bring the shuttle crashing down... At 1:40pm on 10 October, 1989, the four-blade rotor and tail rotor broke off of a helicopter flying above the pine woodlands near Forked River, New Jersey. The craft plunged 2,800 feet to the ground, killing all five passengers. Among them were three of Trump’s top casino executives... With the best managers of his casinos dead, Trump for the first time took responsibility for running the day-to-day operations in Atlantic City. His mercurial and belligerent style made a quick impact – some top executives walked, unwilling to put up with his eccentricities, while Trump booted others. The casinos were struggling so badly that Trump was sweating whether a few big winners might pull him under... executives at the casino were humiliated, since Trump was signalling that he was frightened customers might win... By early 1990, as financial prospects at the casinos worsened, Trump began badmouthing the executives who had died, laying blame on them, although the cause of his problems was the precarious, debt-laden business structure he had built... By June 1990, Trump was on the verge of missing a $43m interest payment to the investors in the Taj’s junk bonds. Facing ruin, he met with his bankers, who had almost no recourse – they had been as reckless as Trump. By lending him billions – with loans for his real estate, his casinos, his airline and other businesses – they could fail if Trump went down. So the banks agreed to lend him tens of millions more in exchange for Trump temporarily ceding control over his multi billion-dollar empire and accepting a budget of $450,000 a month for personal expenditures. In August, New Jersey regulators prepared a report totaling Trump’s debt at $3.4bn, writing that “a complete financial collapse of the Trump Organisation was not out of the question.”.. By December, Trump was on the verge of missing an interest payment on the debt of Trump Castle, and there was no room left to manoeuvre with the banks this time. So, just as he had in the past, Trump turned to Dad for help, according to New Jersey state regulatory records. On December 17, 1990, Fred Trump handed a certified cheque for $3.35m payable to the Trump Castle to his attorney, Howard Snyder. Snyder travelled to the Castle and opened an account in the name of Fred Trump. The cheque was deposited into that account and a blackjack dealer paid out $3.35m to Snyder in gray $5,000 chips. Snyder put the chips in a small case and left; no gambling took place. The next day, a similar “loan” was made – except by wire transfer rather than by cheque – for an additional $150,000. This surreptitious, and unreported, loan allowed Donald Trump to make that interest payment... Trump’s casino empire was doomed. A little more than a year after the opening of the Taj, that casino was in bankruptcy court, and was soon followed there by the Plaza and the Castle. Under the reorganisation, Trump turned over half his interest in the businesses in exchange for lower rates of interest, as well as a deferral of payments and an agreement to wait at least five years before pursuing Trump for the personal guarantees he had made on some of the debt... In 2004, Trump Hotels & Casino Resorts – the new name for Trump’s casino holdings – filed for bankruptcy, and Trump was forced to relinquish his post as chief executive. The name of the company was then changed to Trump Entertainment Resorts; it filed for bankruptcy in 2009, four days after Trump resigned from the board... In his books and public statements, Trump holds up this bankruptcy as yet more proof of his business genius; after all, his logic goes, he climbed out of a hole so deep few others could have done it. He even brags now about how deep that hole was. Trump falsely claimed in two of his books that he owed $9.2bn, rather than the actual number, $3.4bn, making his recovery seem far more impressive... When challenged on the misrepresentation during a 2007 deposition, Trump blamed the error on Meredith McIver, a longtime employee who helped write that book. Trump testified that he recognised the mistake shortly after the first book mentioning it was published; he never explained why he allowed it to appear again in the paperback edition and even in his next book. McIver went on to garner some national recognition as a Trump scapegoat – nine years later, when Trump’s wife, Melania, delivered a speech at the Republican National Convention that was partially plagiarised from Michelle Obama, the campaign blamed McIver. But despite all this supposed sloppiness, Trump has never directed his trademark phrase “You’re fired!” at this loyal employee... In 2008, he defaulted on a $640m construction loan for Trump International Hotel & Tower in Chicago, and the primary lender, Deutsche Bank, sued him. Trump counter-sued, howling that the bank had damaged his reputation... Trump has also based huge projects on temporary business trends. For example, for a few years during the George W Bush administration, wealthy expatriates from around the Middle East flocked to Dubai. In response, Trump launched work on a 62-story luxury hotel and apartment complex on an artificial island shaped like a palm tree. But, as was predictable from the start, there were only so many rich people willing to travel to the United Arab Emirates, so the flood of wealthy foreigners into the country slowed. The Trump Organisation was forced to walk away from the project, flushing its investments in it.Beginning in 2006, Trump decided to take a new direction and basically cut back on building in favour of selling his name. This led to what might be called his nonsense deals, with Trump slapping his name on everything but the sidewalk, hoping people would buy products just because of his brand... Trump hosted a glitzy event in 2006 touting Trump Mortgage, then proclaimed he had nothing to do with managing the firm when it collapsed 18 months later. He tried again, rechristening the failed entity as Trump Financial. It also failed.That same year, he opened GoTrump.com, an online travel service that never amounted to more than a vanity site; the URL now sends searchers straight to the Trump campaign website... Also in 2006, Trump unveiled Trump Vodka, predicting that the T&T (Trump and Tonic) would become the most requested drink in America (he also marketed it to his friends in Russia, land of some of the world’s greatest vodkas); within a few years, the company closed because of poor sales... In 2007, Trump Steaks arrived. After two months of being primarily available for sale at Sharper Image, that endeavour ended; the head of Sharper Image said barely any steaks sold... Amusing as those fiascoes are for those of us who didn’t lose money on them, the most painful debacles to witness were many involving licensing agreements Trump sold to people in fields related to real estate. There is the now-infamous Trump University, where students who paid hefty fees were supposed to learn how to make fortunes in that industry by being trained by experts handpicked by Trump; many students have sued, saying the enterprise was a scam in which Trump allowed his name to be used but had nothing else to do with it, despite his claims to the contrary in the marketing for the “school”... Particularly damning was the testimony of former employee Ronald Schnackenberg, who recalled being chastised by Trump University officials for failing to push a near-destitute couple into paying $35,000 for classes by using their disability income and a home equity loan.Around the country, buyers were led to believe they were purchasing apartments in buildings overseen by Trump, although his only involvement in many cases was getting paid for the use of his brand... In 2010, lenders foreclosed on the $355m project. Even though Trump’s name was listed on the condominium’s website as the developer, he immediately distanced himself, saying he had only licensed his name... A similarly sordid tale unfolded for Trump Ocean Resort Baja Mexico, a 525-unit luxury vacation home complex that Trump proclaimed was going to be “very, very special”. His name and image were all over the property, and he even personally appeared in the marketing video discussing how investors would be “following” him if they bought into the building. Scores of buyers ponied up deposits in 2006, but by 2009 the project was still just a hole in the ground. That year, the developers notified condo buyers their $32m in deposits had been spent, no bank financing could be obtained, and they were walking away from the project. Scores of lawsuits claimed the buyers were deceived into believing Trump was the developer. Trump walked away from the deal, saying that if the condo buyers had any questions, they needed to contact the developer – and that wasn’t him, contrary to what the marketing material implied... The same story has played out again and again. In Fort Lauderdale, Florida, people who thought they were buying into a Trump property lost their deposits of at least $100,000, with Trump saying it was not his responsibility because he had only licensed his name.. Investors in another failed Floridian property, Trump Tower Tampa, put up millions in the project in 2005 believing the building was being constructed by him. Instead, they discovered it was all a sham in 2007, inadvertently from Trump, when he sued the builder for failing to pay his license fees. The investors lost their money, and finally got to hear Trump respond to allegations that he had defrauded them when they sued him. In a deposition, lawyers for the Tampa buyers asked him if he would be responsible for any shoddy construction; Trump responded that he had “no liability” because it was only a name-licensing deal. As for the investors, some of whom surrendered their life savings for what they thought was a chance to live in a Trump property, Trump said they at least dodged the collapse of the real estate market by not buying the apartments earlier.
“They were better off losing their deposit,” he said.
So said the man who now proclaims that Americans can trust him, that he cares only about their needs and their country, that he is on the side of the little guy.