scorecardresearch Skip to main content
Michael A. Cohen

Donald Trump, the con man

Donald Trump meets with energy executives in Denver on Tuesday.MIKE SEGAR/REUTERS

If there is one thing that we’ve learned about Donald Trump, it’s that he is, fundamentally, a con man.

I’m not just referring to the confidence scheme that was Trump University — an elaborate fake university constructed for the singular goal of separating economically vulnerable Americans from their money. Nor am I only referencing to Trump’s entire presidential campaign, which is constructed around the lies he tells about building a wall that Mexico will pay for and, in the process, restoring American greatness.

Rather, I mean the Potemkin Village that is Trump’s global image as a titan of business. This weekend, with the leaking of Trump’s 1995 tax returns and the revelation that he wrote down a whopping $900 million loss, we found out that Trump isn’t just overrated as a businessman — he actually stinks at it.


What’s perhaps most shocking about these revelations is that Trump, the son of a multimillionaire real estate developer, started his business career standing on third base. For him to make money, or at the very least not lose it, was relatively easy.

His startup capital was $1 million he borrowed from his father — and the Trump name, which before Donald got into the family business was fairly strong, at least in elite circles. That’s part of the reason the elder Trump cosigned many of the loans that allowed Trump to make his initial real estate deals (in part because few of Trump’s potential partners trusted him enough).

Trump also took advantage of numerous tax breaks afforded to real estate tycoons in New York City, and he invested in casinos, which are as close to a sure-fire moneymaking business as exist in the capitalist world. Yet with all those advantages, by the mid-’90s he was mired in debt, a victim of one lousy, ill-advised investment after another.


Honestly, how does a guy in the casino business lose close to a billion dollars? To do something like that, you aren’t unlucky — you’re actively bad at your chosen profession.

For New Yorkers, Trump’s lack of business acumen won’t come as a huge shock. In the city he calls home, Trump’s name is synonymous with schlock. His buildings are ugly and are reflective of what someone with bad taste thinks good taste looks like. His casinos in Atlantic City were no different — before they went bankrupt, of course.

That Trump has been able to maintain his wealth and influence is a tribute not to his business skills, but rather his public relations acumen.

Indeed, Trump’s entire business model as an entrepreneur seems built on his telling people that he’s great at business, and people believing him and then putting his name on lots of products (steaks, wines, airlines, universities, casinos, etc.) that further inflate the image of Trump as some sort of capitalist master. That the Trump Shuttle lost millions; that he paid $400 million for the Plaza Hotel and proceeded to sell it 7 years later for $75 million less; that he declared bankruptcy multiple times; and that people who invested in his public business and the creditors who loaned him money lost their shirts, never seemed to register among his fans.

Instead, for millions of Americans, their image of Trump is that of the business leader/CEO of “The Apprentice’’ — a reality TV show based on the fantastical premise that Trump is good at business and surrounds himself with the best people.


It’s what makes the revelations of his business failures so politically devastating. Pretty much the only thing that Trump could fall back on to justify giving him the awesome powers of the presidency is the argument that he’s a great negotiator who could apply his business prowess to matters of state. Instead what we’ve discovered about Trump is that he’s one of the few people in the 1990s who actually lost money. To be sure, Trump’s supposed way around a boardroom has never been a good reason to vote him, as these are the kind of skills that simply don’t translate to matters of state. But even if you’re hanging on to that thin reed, it’s been a bad week.

There is, however, one silver lining. Because of Trump’s write-down on his debt, he was probably able to avoid paying taxes for 18 years. So if the US government ever needs to hire a really good accountant, Trump has just the kind of experience that could come in handy.

Michael A. Cohen’s column appears regularly in the Globe. Follow him on Twitter @speechboy71.