Can’t Stop the Hustle
Why Donald Trump May Never Pay Federal Income Tax Again
The alleged billionaire, last known to have paid up in 1977, may not have to until 2042—if then.
Donald Trump can enjoy income tax-free living for the rest of his life, my new analysis of his tax documents shows, adding to the reasons the Republican nominee for president should make his tax returns public before voting ends next Tuesday.
Thanks to a diligent team of New York Times reporters, we learned Halloween night that Trump’s top-notch tax advisers warned in 1991 that his extremely aggressive tax strategy to convert nearly a billion dollars of taxable income into tax losses would likely be rejected in an IRS audit. But, as we shall see, there was little risk Trump would be audited (doubly ironic, given how he’d used supposed audits to justify becoming the first post-Watergate presidential candidate who hasn’t released tax returns).
The documents in The Times confirm what I told readers a month ago about how Trump transformed taxable income into tax avoidance on a grand scale. Since then, numerous tax practitioners and professors have written their own essays applying the same line of analysis first published in my Oct 3. column, headlined “Art of the Steal.”
That column drew on three pages of 1995 state tax return summary sheets leaked to The Times and the New York Daily News. In its initial report, The Times said that Trump could use $916 million of net operating losses or NOLs shown on those documents to eliminate income taxes for up to 19 years.
What I can now report is that Trump is not restricted to using or losing his tax losses over 19 years but can offset income for as long as he lives.
Based on his 1995 income, Trump could enjoy 47 years of income-tax-free living. That would cover Trump until 2042, when he would turn 96.
But even that understates the situation. As a real estate owner Trump can acquire still more tax losses under liberal rules set by Congress—rules Trump lobbied for—that apply only to full-time managers of their own investment real estate. This means Trump could enjoy a much larger income than the $19 million he reported on his 1995 Connecticut nonresident tax form in future years and still pay no income taxes.
Because of the documents in the latest Times report, it is now beyond question that Trump benefitted from an opinion by Justice Clarence Thomas in a 2001 Supreme Court case infamous in tax circles because it approved the creation of tax losses out of thin air.
Thomas’s decision, in a case involving another business owner who employed much the same strategy Trump had used, violated a basic principle of tax law: that tax losses must have economic substance. To take a tax loss you have to suffer an actual loss. Otherwise people could just put symbols on pieces of paper and fabricate tax losses at will.
But Trump’s advisers figured out a way to take losses suffered by others and turn them into losses Trump could take. Even as the real losers, the banks that got back just pennies on the dollar from their loans to Trump, deducted their actual losses, Trump used those same losses to book his own deductions the documents obtained by the Times show—violating the economic substance doctrine to create double non-taxation.
In his 2001 opinion, Thomas, writing for eight of the justices, noted concerns that taxpayers who used the same strategy as Trump would “wrongly experience a ‘double windfall’:
They would be exempted from paying taxes on the full amount of the discharge of indebtedness, and they would be able to increase basis and deduct their previously suspended losses.”
But, Thomas wrote, that was not the court’s concern. It is a position I find as wanting as the overly technical justifications for many of the tax shelters I have exposed.
Justice Thomas’s opinion was so egregiously at odds with economic reality that a few months later Congress—in a Republican-sponsored bill—shut down any further use of the scheme Trump employed. A simple explanation of the complex strategy was provided by the Congressional Joint Committee on Taxation at printed page 28.
But while Congress stopped further abuse with passage of the Job Creation and Worker Assistance Act of 2002, it did not apply the new law retroactively nor did it limit losses to the date the bill was introduced. As it so often does, Congress
belatedly closed the tax barn door with no effort to make those who had already fled the tax system come back and pay in the future.
Thanks to the way Thomas wrote his opinion, Trump is not limited to the 19 years but can live income tax-free provided his lifetime income starting in 1995 does not exceed $916 million.
But even if his income after 1995 exceeds that number, he can still live tax-free because he benefits from a special tax rule, one he lobbied for, that applies only to wealthy real estate owners who manage their own properties.
Indeed, the losses could even be used after Trump’s time runs out to shelter his money from federal and state taxes that might otherwise be owed by his estate.
The key to all of this was official favoritism by the State of New Jersey, which created the image of being a tough casino regulator by going after little people like cocktail waitresses and blackjack dealers while enabling misconduct by owners, especially Trump.
In 1990, when Trump claimed he was worth $3 billion—yet he could not pay his bills—he persuaded New Jersey casino regulators to take his side against his bankers. Politically that choice was easy. Trump was a major employer in Atlantic City, while of the 70 banks he owed money only two were in New Jersey.
The banks reduced the debt Trump personally guaranteed from close to $1 billion down to $115 million.
Normally when one borrows money and does not pay it back, the unpaid balance is immediately taxable as income.
Trump’s strategy was to assert that the forgiven debts flowed through to his companies and changed not his income, but his balance sheets. The plan outlined in a 47-page Wilkie Farr & Gallagher opinion letter reproduced by The Times was more warning than endorsement of this tax strategy.
Trump, who is last known to have paid federal income taxes in 1977, was at little risk of the audits that the Wilkie firm warned him about. An analysis Syracuse University Professor Sue Long, co-director of the Transactional Access Research Clearinghouse, did this morning, at my request, of data that the IRS is required by court order to turn over to her shows how small the audit risk is even for wealthy people like Trump. In many years, fewer than one in 10 tax returns with positive incomes of $1 million or more get audited. Using TRAC data, I calculated that of the millionaire tax returns audited last year, the average examination lasted just 17.1 hours.
That means, statistically, that even if Trump’s tax return was audited last year an agent could spend less than one minute on each of what Trump says were more than 1,200 pages he filed with the IRS.
Trump’s audit risk was actually much smaller than that. We know Trump in recent years reported less than $500,000 on his tax return because he collected a New York state homeowner tax benefit given only for those who report less than that. Indeed, he may have reported negative income, as he first did in 1978.
Trump claims he is under audit, but he declines to release the form letter which would declare that. In other words, there is exactly no evidence that Trump is or has been under audit for his personal federal income tax return, just as no verifiable evidence exists that he is, or ever was, a billionaire.
Trump says that not paying income taxes shows that he is “smart.” I say it is outrageous because the rest of us have to pick up the burdens that Trump shirks, making us subsidize him.
The fact that he alone among every major party nominee for president going back more than 40 years refuses to make public any of his tax returns raises reasonable questions about whether he is a tax cheat. Trump’s tax attorney, Jack Mitnick, disavowed the Republican candidate’s 1984 tax return, a story this column broke in June.
That Trump and some others live large while paying no federal income tax for years—or even their entire lives—adds to the many reasons that we need to junk our century-old tax code. We cannot reform our existing federal tax code, either economically or politically, to serve our national needs. My next book, “The Prosperity Tax,” lays out a plan to fix this while encouraging investment and job creation, shrinking the IRS and, most of all, making sure everyone who has a large income pays income taxes.
Trump, on the other hand, vows that if elected he will cut taxes on the rich. For people like Trump that may be smart. For the rest of us, though, it’s dumb and dumber.