Donald Trump in 2015
Andrew H. Walker/Getty Images

The 2016 election’s first manufactured “October surprise” is a full-length investigative story from the New York Times about Donald Trump's taxes. More specifically, the fact that after running up almost a billion dollars in losses and debts in 1995, Trump has likely not paid any taxes in almost 20 years. This in and of itself isn’t the problem; what is the problem is that Trump is running on the promise of ending the very system that made him rich, and nobody in his or her right mind can believe him after this revelation.

The Times story is pretty extensive. Using just three pages of a 1995 tax return that was sent from an anonymous source in Trump Tower, the journalists managed to piece together a pretty fascinating story. Trump posted losses of over $916 million in 1995, around the time his casinos, airline and several other business ventures went belly up. Under tax laws at the time, you could spread out losses over several years to essentially avoid paying any federal taxes. A business that shows a “loss” every year is basically tax free, and as a “genius” businessman, Trump probably used every legal and quasi-legal trick in the book to get out of paying Uncle Sam anything. Something that, according to Trump, makes him smart.

Let’s step back for a moment and think about what this really means for the average person. Nobody likes paying taxes. In fact, most Americans who pay any taxes do whatever tricks they can to lower their tax burden. If you have the time, and an inclination, you can write off almost anything. If a home improvement is tax-deductible, why not add in the lunch you got with your husband on the way to Home Depot to look at some paint swatches? Nobody at the IRS is going to notice that, right?

So when Trump says he’s smart for not paying taxes, there is a certain logic to it that the average American can understand. Paying taxes is like traffic laws: We all know they’re there for a reason, and they are ultimately for the public good, but everyone is always trying to find a way around them. Those who can nobly claim that they proudly or happily pay their taxes out of a commitment to the common good aren’t trying to live off of a $290 paycheck every week with $72 taken out for taxes.

Of course, when you make $290 a week, it’s OK to grouse about $70. When you make $29,000 a day, it’s hard to believe that you can justify welshing on your taxes. Trump’s whole campaign has been based on a logical, if not somewhat arrogant and white-privileged notion, that since he’s the expert at gaming the system, from politics to economics, he’s the perfect vessel to actually change that system. But what his tax information exposes, yet again, is that there is no reason to believe that Trump would do anything to tear down the very system that made him rich.


His whole campaign is the equivalent of a guy breaking into your house and stealing all your stuff and then coming back a week later and offering his services for your home security. In theory he clearly knows what he’s doing. In practice, why should you trust a guy who broke into your house?

The Times story would be less of an issue if Trump’s proposed tax plans actually did something about the very loopholes he’s used to get rich and stay that way, but they don’t. And while Trump claims that he’ll create new tax policies to let all Americans get a bigger piece of the economic pie, if Trump University is any indicator, he does a lousy job of sharing his secrets of success.

Speaking of secrets, the impact of the Times story only makes Trump’s refusal to release his taxes appear all the more damning. If reporters can figure out that he ran up a billion dollars in debts and then likely didn’t pay taxes for 20 years based on three pages, what would happen if even 10 years of information came out? Not only would it likely indicate that he doesn’t have Bruce Wayne money, as Hillary Clinton hinted, but ethically, his tax record would probably fall somewhere between Lucious Lyon on Empire and Jack Donaghy on 30 Rock (with, perhaps, a few too many connects with Milan from Power).


The presidential race will not be changed because of the New York Times piece on Trump’s finances. The polls for him in Ohio will not suddenly shift to Hillary Clinton; nor will this result in some huge implosion of Team Trump. However, as we bear down into the last 30 days before we select the new leader of the free world, Trump’s refusal to follow basic patterns of campaign norms are coming back to haunt him. In the meantime, I hope his few minority supporters don’t get it in their heads to follow Trump’s tax advice. That doesn’t work out nearly as well for black people.

Make sure you protect your vote in this critical election for America. Learn more about how to register and protect your vote here.

Jason Johnson, political editor at The Root, is a professor of political science at Morgan State’s School of Global Journalism and Communication and is a frequent guest on MSNBC, CNN, Al-Jazeera International, Fox Business News and SiriusXM Satellite Radio. Follow him on Twitter.