Trump Bragged Nonstop About His Success While Quietly Hemorrhaging Millions

President Donald Trump was perhaps the single greatest loser of money from 1985 to 1994, a bombshell New York Times investigation into his tax returns found Tuesday. But despite but the $1.17 billion he bled out on failed casinos, hotels and retail space during that time, he spent the decade telling Americans — the people who would one day elect him as their president — that he was a resounding success. 

“There is no one my age who has accomplished more,” he boasted to Newsweek for a cover story in 1987, a year his business losses compounded to $4.5 million.

By that time, Trump had already been self-mythologizing about the basis of his wealth for years. “Some people have an ability to negotiate,” he told The Washington Post in 1984. “It’s an art you’re basically born with. You either have it or you don’t.”

Though Trump has long characterized himself as being self-made and claimed he only received $1 million from his father to launch his empire, investigations into his early earnings show he actually received about $413 million in 2018 dollars from his father, who repeatedly deployed financial safety nets to his son while helping him engage in lucrative tax schemes.

The same year Trump gave that interview to Newsweek, he released “Trump: The Art Of The Deal,” a memoir and business advice book that was integral in launching his career in the public eye. He began working on the book with a co-author in 1985. That same year, Trump’s business losses had mounted to $51.4 million.

The book ― the first of several business advice works he’d go on to publish ― helped make Trump a fixture on various talk shows. In a sit-down with David Letterman in 1988, a year Trump’s compiled losses totaled $46.6 million, Trump smiled along with the raucous laughter from the audience when Letterman asked him whether there was “any way a guy like you could go broke.”

“I would like to think that I could weather most [disasters],” Trump said, adding, “I think it’s a great time to have cash.”

Trump portrayed similar stability during a 1989 interview with The Chicago Tribune.

“Vision is my best asset. I know what sells. I know what people want,” he continued ― a self-assessment he’d make again in later interviews. 

“Even if the world goes to hell in a handbasket, I won’t lose a penny,” he mused. 

He was drowning in $90.3 million in losses by that year, and the worst was still yet to come. Trump’s financial losses reached stunning lows in 1990, when his business losses mounted to $400.3 million. 

Nevertheless, he waxed philosophical about what important role models rich men like him were to the average Joe during a lengthy interview with Playboy that year. 

“The working man likes me because he knows I worked hard and didn’t inherit what I’ve built,” Trump said, stretching the truth about his own success. “Hey, I made it myself; I have a right to do what I want with it.”

When asked why he flaunts his wealth so much, Trump said he sees himself as an inspiration of wealth to others. 

“A display is a good thing,” he said. “It shows people that you can be successful. It can show you a way of life … It’s very important that people aspire to be successful. The only way you can do it is if you look at somebody who is.”

He also offered up what’s perhaps one of his most Trumpian adages to date: “Rich people are great survivors.” 

By 1991, when his losses over the years totaled $664.3 million, Trump appeared to be struggling to keep up the charade as critics worried his Trump Palace project, a 55-story condominium building he was constructing in Manhattan, would flounder like his other failed projects. 

He responded, the Times found, by buying out advertisements calling the project “the most financially secure condominium on the market today” and promising that “smart money says there has never been a better time.”

The Times’ bombshell report only offers a glimpse at one decade of Trump’s finances, which it obtained from a source “who had legal access to it,” the paper said. In a break with longstanding precedent, the president has not voluntarily released any of his federal tax returns and has not cooperated with House Democrats over their request that he release them. 

Lawmakers in 19 states have introduced legislation that would require Trump to release them if he wants to appear as a candidate on the 2020 ballot. 

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