(Brendan Smialowski/AFP/Getty Images) (Afp Contributor#afp/AFP/Getty Images)
Opinion writer

In 2011, Donald Trump agreed (for a hefty fee) to be roasted by Comedy Central, with one stipulation for the show. The comedians participating could joke about just about anything, including his hair, his racism and even the idea that he lusted after his own daughter.

There were two related topics, however, that Trump forbade them to joke about. They could not needle him for his business bankruptcies, or for being less wealthy than he claimed.

I couldn’t help but think about that story as I read the latest revelation about President Trump’s finances from the New York Times, based on printouts from official IRS documents it obtained from the 1980s and 1990s. The new documents provide yet more evidence of the true nature of Trump’s con, one he has sustained for an entire career:

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.

In fact, year after year, Mr. Trump appears to have lost more money than nearly any other individual American taxpayer, The Times found when it compared his results with detailed information the I.R.S. compiles on an annual sampling of high-income earners. His core business losses in 1990 and 1991 — more than $250 million each year — were more than double those of the nearest taxpayers in the I.R.S. information for those years.

Over all, Mr. Trump lost so much money that he was able to avoid paying income taxes for eight of the 10 years.

The documents cover only the broad picture of Trump’s income and losses in those years, not the details. But they demonstrate once again why it is so critical that the public obtain his full tax returns for more recent years. As Trump fights like a cornered mongoose to keep those returns secret, these documents offer hints about what exactly he’s trying to conceal.

As I’ve often said, if Trump’s tax returns showed only that he is a successful and shrewd businessman, he’d have plastered them on a billboard in Times Square. He is hiding something; the only question is how bad it is.

There are two explanations for what Trump is trying to conceal. The first is that there are scandalous or even criminal activities that he has engaged in — partnerships with shady characters, cases of money laundering — and the returns would point the way to discover them.

To understand why, you have to remember that the Trump Organization is not an ordinary corporation in the way you might think of it. In fact, it is an amalgam of approximately 500 separate partnerships and pass-through companies (which is why Trump almost certainly reaped millions of dollars in tax benefits from the 2017 tax law, which included a 20 percent deduction for pass-throughs). If we had Trump’s returns, each of those arrangements could be investigated, and no one who has reported on Trump’s business activities would say there aren’t shocking things to discover.

The second explanation for Trump’s determination not to allow the returns to become public is in some ways more innocent: that as so many have speculated, he’s not nearly as rich as he always says. Is it possible that Trump’s motives are only the most petty, shallow and vain ones? After all, we’re talking about Donald Trump.

Of course, both things could be true. Trump’s returns could show him to be less wealthy than he says, and also reveal instances of scandalous or criminal behavior. If I had to hazard a guess I’d say that’s what’s most likely. But let’s look at how Trump himself reacted to this story:

This is a bizarre defense. Trump seems to be claiming that it was shrewd for him to lose hundreds of millions of dollars, because he was doing it to avoid paying his taxes. The next time you see taxes deducted from your paycheck to pay for everything from the military to farm subsidies to health care for children, you might recall that he says of his own successful efforts to avoid paying taxes, “it was sport.”

Even here, however, there may be evidence that Trump did more than simply exploit loopholes in the tax code. As Steve Rosenthal of the Tax Policy Center points out, Trump was taking enormous tax deductions on losses of other people’s money. But when the loans he couldn’t pay back were restructured or forgiven, he would have had to declare those funds he was no longer responsible for paying as income, and pay taxes on it.

Did he? We don’t know. We do know, however, that Trump believes paying taxes makes you a sucker. When Hillary Clinton suggested that he wasn’t paying any taxes, he responded, “That makes me smart.”

We also know from an extensively documented New York Times investigation that Trump, his father, and his siblings executed a scheme to defraud the government of hundreds of millions of dollars in tax revenue in the 1990s.

Trump’s own personal greed and his sense that the rules don’t apply to him have never been in question. But why would he be so threatened by people learning that he isn’t as wealthy as he claims? Part of it is ego, of course; he plainly equates money with one’s value as a human being. But it’s also because he built his career on the belief that if he could convince people he’s impossibly rich, he’d become impossibly rich and remain so.

That’s what Trump has always sold, whether it was to the people he conned out of their life savings with Trump University or to the voters. I am hugely wealthy and hugely successful, and if you associate yourself with me you will reap the reflected rewards.

And if Trump isn’t so wealthy after all, what is he? A small-time grifter, a business failure, a gossip-pages lech, a reality-show buffoon.

That’s what he’s hiding, for sure. And maybe much more.

Read more:

Jennifer Rubin: Five takeaways from Trump’s reported billion-dollar loss

Paul Waldman: Trump’s tax return scam has taken yet another turn

James Downie: The wonderful illogic of Trump’s hidden tax returns

Paul Waldman: Getting Trump’s tax returns is only the beginning

Greg Sargent: The case for getting Trump’s tax returns just got stronger — and more urgent