Donald Trump has broken with two generations of precedent by refusing to release his income tax returns, but some 1995 tax documents leaked to the New York Times and published on Saturday night both offer some valuable insight into his finances and a window into why Trump may not want us to know more.

The leaked documents are not complete tax returns. Instead, they are the first pages of Trump’s New York, New Jersey, and Connecticut state tax returns from 1995. Consequently, they don’t really offer any details in terms of the specifics of what Trump claimed 20 years ago. What they do show is an eye-popping loss of $916 million — a loss that tax rules would have allowed Trump to spread across multiple years to cancel out up to $50 million a year in income over an 18-year span.

As the Times explains, there’s no indication in these documents that Trump did anything improper. He really did have a number of businesses fail in the early ’90s, and federal law does allow wealthy individuals to take net operating losses from partnerships they own and use them to cancel out personal income.

But simply as a matter of appearances, it is probably a bad look for Trump to admit publicly that he has been living a lavish lifestyle while having paid $0 in federal income taxes for some undetermined number of years. Many of us, after all, seem to manage to pay taxes while enjoying a distinctly non-Trumpian lifestyle.

We learned previously from documents Trump filed to gain a casino license in New Jersey that he paid no taxes for a couple of years in the late 1970s, while separate licensing documents indicate the same for a couple of years in the early 1990s.

The Trump campaign, in an angry statement, seemed to confirm the authenticity of the documents by arguing that they were illegally obtained. The statement also indicates that Trump “has paid hundreds of millions of dollars in property taxes, sales and excise taxes, real estate taxes, city taxes, state taxes, employee taxes and federal taxes, along with very substantial charitable contributions.”

That appears to be an implicit admission that he has, in fact, gone long stretches at a time while paying little or nothing in federal income taxes. And while it’s certainly true that he has paid other taxes over the years, it’s also true that he’s received nearly $1 billion in tax subsidies for his various projects.

“That makes me smart”

During the first presidential debate against Hillary Clinton, she suggested that non-payment of taxes may be one of the reasons Trump is reluctant to release his returns. Trump replied that if he had avoided paying taxes in the past, that was a sign of his intelligence.

Here’s their full exchange (emphasis added):

CLINTON: I think you've just seen another example of bait and switch here. For 40 years, everyone running for president has released their tax returns. You can go and see nearly, I think 39, 40 years of our tax returns — but everyone has done it. We know the IRS has made clear there is no prohibition on releasing it when you're under audit. So you've got to ask yourself, why won't he release his tax returns? And I think there may be a couple of reasons. First, maybe he's not as rich as he says he is. Second, maybe he's not as charitable as he claims to be. Third, we don't know all of his business dealings but we have been told, through investigative reporting, that he owes about $650 million to Wall Street and foreign banks. Or maybe he doesn't want the American people, all of you watching tonight, to know that he's paid nothing in federal taxes, because the only years that anybody has ever seen were a couple of years when he had to turn them over to state authorities when he was trying to get a casino license and they showed he didn't pay any federal income tax. So… TRUMP: That makes me smart. CLINTON: He paid zero. That means zero for troops, zero for vets, zero for schools or health. And I think probably he's not all that enthusiastic about having the rest of our country see what the real reasons are because it must be something really important, even terrible, that he's trying to hide. And the financial disclosure statement — they don't give you the tax rate. They don't give you all the details that tax returns would. And it just seems to me that this is something that the American people deserve to see, and I have no reason to believe that he's ever going to release his tax returns because there's something he's hiding. And we'll guess, we'll keep guessing at what it is that he's hiding, but I think the question is, will he ever, to get near the White House, what would be those conflicts? Who does he owe money to? Well, he owes you the answers to that and he should provide them.

You see here a contrast between a business person’s point of view, in which tax minimization strategies are, indeed, smart, and a politician’s point of view, in which it’s not wise to imply that ordinary middle-class people who pay taxes every year are being stupid. A person in Trump’s position could conceivable square the circle by running on a tax reform program that would be bad for him personally, but Trump’s actual tax plans imply massive reductions in the amount paid by rich people even while taxes would go up on millions of working- and middle-class families.