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The myth of Donald Trump’s success in business is shattered

The Rachel Maddow Show, 5/7/19, 9:07 PM ET

Trump red line failing despite urgency to keep finances opaque

Rachel Maddow shares details from a new blockbuster report from the New York Times about what Donald Trump’s taxes show about the bleak state of his business affairs from the mid-1980s to the mid-1990s, and notes that Trump’s best efforts to keep his
Last October, the New York Times first published a devastating report on Donald Trump’s finances. As regular readers may recall, the newspaper’s exhaustive research uncovered evidence of “dubious tax schemes” and “outright fraud” that Trump exploited to receive hundreds of millions of dollars from his father.

The findings painted a picture in which the president, far from the self-made man he pretends to be, relied heavily on legally dubious family handouts. It was brutal, not just because of the evidence of financial wrongdoing, but also because it exposed Trump as a fraud. The self-aggrandizing myth of the New Yorker as a private-sector genius was shattered.

Last night, the Times advanced the story in ways that made matters even worse for Trump, shining a light on previously unrevealed figures from the president’s finances between 1985 through 1994.

By the time his master-of-the-universe memoir “Trump: The Art of the Deal” hit bookstores in 1987, Donald J. Trump was already in deep financial distress, losing tens of millions of dollars on troubled business deals, according to previously unrevealed figures from his federal income tax returns.

Mr. Trump was propelled to the presidency, in part, by a self-spun narrative of business success and of setbacks triumphantly overcome. He has attributed his first run of reversals and bankruptcies to the recession that took hold in 1990. But 10 years of tax information obtained by The New York Times paints a different, and far bleaker, picture of his deal-making abilities and financial condition.

By all appearances, Donald J. Trump was an unusually bad business man. The Times report added, “The numbers show that in 1985, Mr. Trump reported losses of $46.1 million from his core businesses – largely casinos, hotels and retail space in apartment buildings. They continued to lose money every year, totaling $1.17 billion in losses for the decade.”

The article went on to note that during this period, Trump “appears to have lost more money than nearly any other individual American taxpayer.”

Or put another way, Trump wasn’t just a loser in business, he was among the biggest losers in the country. Voters who backed the Republican because they saw him as a private-sector success story fell for a brazen scam.

While he was failing spectacularly, losing money at an extraordinary pace, this was a period in which Trump cultivated an image as a private-sector titan. Trump’s “brand” as a successful businessman – which he continues to exploit – was little more than a mirage. The persona was a cardboard cutout, which Trump hid behind, hoping no one would notice the scope and scale of his failures.

Why should you care about the president’s failures from that era? A few reasons, actually. First, Republican criticisms in 2016 about Trump being little more than a “con man” are now even easier to accept as true. MSNBC’s Chris Hayes asked on Twitter last night, “He’s got to be, quite literally, the most successful con artist of all time, right? Who comes close?”

Second, Trump continues to move heaven and earth to keep his financial history secret. We’re starting to get a better sense of why he’s engaged in such extraordinary efforts, and in the background, we’re left to wonder what more we might learn from the materials the president continues to hide.

Third, while we’re learning a lot, there are new questions about some of the details, including a “particularly hard to explain” anomaly: “the $52.9 million in interest income he reported in 1989.”

And finally, as congressional Democrats seek information on Trump’s financial history, it’s increasingly difficult for his allies to suggest there’s no point to the line of inquiry. The president climbed the ladder through a series of schemes, bluffs, and scams, failing repeatedly, despite having every advantage, while quietly pretending otherwise.

There’s no shortage of legitimate questions about where and how Trump got all of this money, and the degree to which his many financial setbacks left him vulnerable to manipulation.

Donald Trump and Scandals

The myth of Donald Trump's success in business is shattered