Do Trump’s Taxes Show He’s a Failure, a Cheat, or a Criminal?

Three possible explanations for why he only paid $750.

An illustration of Donald Trump with a tax-returns-and-money collage
Getty / The Atlantic

The New York Times exposé of President Donald Trump’s taxes is chock-full of tantalizing revelations. According to the report, the president avoided paying federal income tax in 10 of the 15 years preceding his election. In 2016, he paid $750 in federal income tax, less than one night’s stay in a suite at the Trump International Hotel in Washington, D.C.

But the story also left some big questions unanswered. How exactly has a self-declared billionaire avoided federal taxation for the better part of this century? Do these records prove that he’s poor, or astonishingly good at hiding how rich he is? And what’s the deal with all the money he’s losing on golf courses?

When I talked with several tax experts recently, including some with direct knowledge of Trump’s past tax records, three somewhat overlapping interpretations emerged: incompetence, malfeasance, and criminality. I wrote most of this before the president fell ill. It feels awkward to focus on this now, but on the eve of an election, the American people need to understand the questions swirling around the president’s finances. I hope the president fully recovers, and provides us with some answers.

Explanation 1: Trump’s businesses are doing terribly

One rather literal interpretation of Trump’s tax records is that Trump is a pretty bad businessman, full stop.

Since 2005, Trump has made hundreds of millions of dollars from The Apprentice and associated branding deals. He’s poured much of it into risky investments that have ostensibly failed, and he’s used those losses, on top of business deductions, to drive down his taxable income. In this way, he’s marshaled business failures to zero out his income taxes.

But the scale of Trump’s losses still stunned the tax experts I interviewed. “His losses are staggering, especially for somebody in real estate, for whom the tax code is very generous,” said Steve Rosenthal, a senior fellow at the Urban-Brookings Tax Policy Center, who has studied Trump’s tax returns from the 1990s. “In part, this reflects the changing nature of Trump’s business operations. He used to be a pure real-estate mogul. But in the last 15 years, he’s made more money as a television star who licenses his name to various products. He’s been incredibly unsuccessful at owning and operating stuff in that time.”

Trump is no stranger to losing money. Tax forms obtained by The New York Times showed that, from 1985 to 1994, Trump lost “more money than nearly any other individual American taxpayer.” But his net worth is estimated at $2.5 billion. He’s clearly very rich! So how has a clearly very rich person avoided paying income taxes for the better part of this century?

Explanation 2: Extremely questionable tax maneuvering

Trump claims business deductions like Louis XIV furnished Versailles: lavishly, laughably, with monarchical prerogative. For instance, Trump deducted $70,000 in hairstyling expenses. “The tax law is clear that you don’t get to claim a business deduction for expenses that are fundamentally personal in nature,” said Ari Glogower, a tax-policy professor at the Ohio State University. “It’s the same principle that says you can’t deduct fancy suits just because you work in a nice office.”

More egregious, Trump seems to have paid $700,000 in “consulting fees” to his daughter, Ivanka—a sum he also claimed as a business deduction. “There could be a variety of games going on there,” Glogower said. “It could be about avoiding estate taxes, or avoiding payroll taxes, or avoiding state taxes. We need more facts to know for sure, but shifting income to your family through unearned consulting fees is a classic tax game, which Fred Trump used as well.”

Those examples, although garish, are small potatoes compared with Trump’s treatment of debt. Across decades, Trump honed a simple, devious strategy. He borrowed lots of money, lost it on failed investments, and took huge deductions on interest, depreciation, and operating expenses, which drove down his federal income tax. Very often, he would declare bankruptcy or otherwise renegotiate the terms of the original loan to avoid paying it back in full.

What’s so wrong—or deviously clever—about all that? Well, Trump’s trick, according to Steve Rosenthal of the Tax Policy Center, is all about what he did after the bank wrote down his debt. “So Trump would borrow money from banks, spend it all, and go back to his creditors and find a way to avoid paying the whole loan back,” said Rosenthal. “But when a bank writes off your debt, the discharged debt is income. You have to report it as taxable income. Trump never did.”

Instead, Trump repeatedly ducked his obligations to lenders and the IRS, perfecting the same playbook—borrow, spend, deduct, and walk away. Eventually, American lenders caught on to the gambit and stopped giving him money, forcing him to seek other sources of revenue, such as Deutsche Bank and international plutocrats.

And that’s where, just maybe, things took a criminal turn.

Explanation 3: A mystery only prosecutors can unwind

Starting about 10 years ago, the so-called King of Debt tried something new: spending his own money. He spent up to $400 million buying golf courses, hotels, and wineries. He also took on $400 million in personally guaranteed loans, exposing him to personal bankruptcy in the (very common!) event that he can’t pay back the loans in full.

These decisions are unusual for private real-estate companies, which typically take advantage of debt through the tax code and funnel their largest investments through partnerships that protect individual investors from personal bankruptcy. What’s more, it’s not clear how Trump suddenly came up with all of that cash. Eric Trump told The Washington Post that his father “had incredible cash flow and built incredible wealth….He didn’t need to think about borrowing for every transaction. We invested in ourselves.” But The New Yorker’s Adam Davidson wrote in 2018 that “The portfolio of assets that Trump owns does not suggest that he would have so much money that he can casually spend a few hundred million on a whim.”

It gets even weirder. All those golf properties look like horrendous businesses, having declared losses of more than $315 million since 2000, according to Trump’s tax records. In short, Trump is pouring a mysteriously large amount of money into opaque businesses suffering mysteriously high losses.

None of the tax experts I talked with said: “Yep, that’s clearly an illegal scheme.” But several told me that when companies, such as golf courses or restaurants, that seem to be losing lots of money nevertheless continue in operation for many years, prosecutors might become interested in investigating money laundering.

What is money laundering, exactly? Say I’ve got $10 million in illegally earned cash. What am I going to do with it? Buy a condo? Uh, no, the IRS will sniff that one out. So I have to find a way to hide this cash; to mix my dirty money with some clean money; to launder it. So I give my $10 million to a clever guy I know. I don’t want to buy anything from my pal directly. I want him to buy something else with my $10 million that produces a steady flow of clean money, such as a golf course that brings in $2 million a year in revenue. Every December, my pal takes $100,000 of that revenue for himself and sends me $900,000; the golf course keeps only half its income. Voila! I’ve turned my $10 million of dirty, un-spendable money into $900,000 of clean, beautiful cash flowing into my account, every year. Also, because the golf course is sending out 50 cents on every earned dollar to a couple of crooks, it’s going to look like a terrible business.

If Trump’s golf courses and other properties were serving as money-laundering enterprises for (let’s say) Russian oligarchs, we would expect to see three things: mountains of cash materializing from basically nowhere, several large money-losing enterprises, and a disinclination to abandon those failing properties. We’re seeing all of that.

Brian Galle, a tax professor at Georgetown University, told me that my three explanations aren’t mutually exclusive. “There is a relationship between your interpretations one, two, and three,” he said. “If you’re a naturally successful businessperson, there is less pressure to maintain your wealth with tax-evasive maneuvers, or to engage in full-fledged money laundering.”

Trump’s tax records are a clue, not a complete answer. Their incompleteness might be the most concerning thing about them. “As a citizen, my reaction to the Times report is: The president owes a ton of money, and we don’t know who he owes it to,” Galle said. “Many of his creditors are effectively shells, and it’s opaque who the parties and interests are. Maybe there shouldn’t be a freak-out, because he owes it all to Deutsche Bank. And they’ve never been involved in money laundering, right? Oh, that’s right.