A Con Man of Epic Proportions

Donald Trump Costume Institute Gala Benefit, Celebrating 'Alexander McQueen: Savage Beauty' at the Metropolitan Museum of Art, New York, America - 02 May 2011 (Rex Features via AP Images)
Start your day with TPM.
Sign up for the Morning Memo newsletter

This story has been known in its outlines for many years. But with this weekend’s Times revelation it takes on a new relevance. In short, it is the story of how Donald Trump ran his Atlantic City-based casino empire into the ground but managed to survive and rebound by finding other people to assume his debts. It’s a highly revealing story about Trump the man and businessman because it’s hard to believe the totality of what happened didn’t involve committing some serious crimes. But it’s also the critical backstory to that loss of almost $1 billion which appears to have allowed Trump to avoid paying income taxes almost ever since.

The Post has a good run-down of the details of what happened. Here’s an overview. Trump ran into severe financial difficulties with his casinos in the early 90s, running up a massive amount of debt even as others were making a killing in the casino business. He avoided personal ruin in part by getting the banks who backed him to forgive a lot of the debt. But he also tricked members of the public into taking over his failed businesses.

Again, the Post has the details. But the gist is that Trump set up his first major public company Trump Hotels and Casino Resorts. It was listed on the NYSE and members of the public, including quite a few individual investors, bought the stock. It was an IPO of a mature, indeed already failing company. But Trump used the allure of the Trump name to entice people in.

Over the next several years the businesses swirled down the drain and Trump was able to sell his other distressed casinos to the public company. In other words, he was both the buyer and the seller. So he sold the deeply indebted and already failing Trump Taj Mahal and Trump Castle to the company at a price of his choosing. While he was doing this he continued to pay himself tens of millions of dollars a year as the company’s CEO in addition to using the company to help out his other businesses. By all these machinations he managed to have the company’s major expenditures be paying off or at least servicing the debts he had racked up before the public company came into existence. At the end of the day basically everyone who invested in Trump company lost everything.

The company launched in 1995, the same year Trump claimed almost a $1 billion in losses on his tax return. Clearly these two things were related. Indeed, the Casino business was the essence of Trump’s business empire at that point. We just don’t know precisely how it all fits together because unlike the public company which had to make all the filings every public does, Trump’s personal finances are private and remain that way because he’s refused to release his tax returns.

As I noted yesterday, given the massive scale of the losses in a single (though pivotal) year and Trump’s penchant for aggressive financial dealings (to put it generously), my question is whether those losses were ‘real’ losses he sustained as opposed to paper losses he did not. To put it more concretely, these loss carry forwards are supposed real losses – as in you invested a billion dollars of your own capital and lost it. There are other ways to legitimately generate losses – through depreciation and other ways. But the IRS and all major taxing authorities have ways of preventing you for benefitting from losses you didn’t actually sustain. The options run the gamut from completely legitimate to obviously illegal. If it’s true, as Trump claims, that he’s been continually under audit, it seems likely that anything obviously illegal would have been caught. It’s also possible that the on-going audits have been disputes over the losses and tax benefits Trump was claiming. We don’t know.

At the risk of stating the obvious, we need to see Trump’s tax returns. Indeed, it is no exaggeration to say that we’ve been more in need of seeing Trump’s tax returns than any president in American history.

Latest Editors' Blog
Masthead Masthead
Founder & Editor-in-Chief:
Executive Editor:
Managing Editor:
Associate Editor:
Editor at Large:
General Counsel:
Head of Product:
Director of Technology:
Associate Publisher:
Front End Developer:
Senior Designer: