Dana Milbank: What tax tricks are up Trump’s sleeve?

A generation after Ronald Reagan denounced the “welfare queen,” the Grand Old Party is evidently on the verge of nominating its first welfare king.

Four years ago last week, the party’s 2012 presidential nominee, Mitt Romney, famously wrote off the 47 percent of Americans who don’t pay federal income taxes. Romney, secretly recorded at a fundraiser, said the 47 percent “who are dependent upon government” won’t vote for him because “I’ll never convince them that they should take personal responsibility and care for their lives.”

Now, just one presidential cycle later, Republicans have settled on a presumptive nominee who is himself among the 47 percent of non-taxpayers. Trump has been refusing to release his tax returns, and we have a pretty good idea why: He has been feeding at the public trough.

The Washington Post’s Drew Harwell reported that, for at least two years in the late 1970s (the last time Trump’s tax information was made public), Trump paid no federal income taxes. Several tax experts I spoke with said it’s entirely possible that Trump has continued to report negative income – and therefore not pay taxes – because of loopholes and dubious deductions that benefit powerful real estate interests. They say it’s likely that whatever taxes he does pay would be at a rate lower than the average worker pays.

That’s typical for Trump’s line of work. Because of depreciation, the deductibility of interest and other tax breaks, the effective tax rate on the real estate sector is lower than most industries, and in some cases negative.

There is no shame in being on public assistance. The earned-income tax credit, which subsidizes low-income workers and has helped millions out of poverty, is the main reason for the 47 percent (though they still have state, payroll and other taxes). But the corporate welfare Trump receives is nothing to be proud of – not least because Trump has claimed to represent the American worker and has condemned corporate executives who “make a fortune” but “pay no tax.”

Investors, such as Trump, can write off depreciation of investment properties even if those properties actually increase in value, and because most real estate development is financed with debt, they can deduct the interest. Instead of selling buildings, they can incorporate them and make “like kind” exchanges that defer capital-gains taxes indefinitely. Trump, depending on how he structures his taxes, may also be avoiding taxes by amortizing his name as an intangible asset. And, because his brand is his main asset and his business interests are far flung, he could argue that virtually all of his expenses are business related, and therefore deductible.

“I’d be shocked if he isn’t pretty much writing off his whole life,” said Bob McIntyre, head of Citizens for Tax Justice. “When you can write off your income and write off your consumption, you’re in a Leona Helmsley situation.” The late Helmsley, who also had a real estate fortune, is remembered for observing that “only the little people pay taxes.”

Trump, who would be the first presidential nominee in 40 years not to release his returns, says he’s refusing because he’s being audited. But an audit doesn’t prevent him from releasing returns, and he won’t release returns from years not under audit, either. “It’s not because he’s being audited,” said Roberton Williams of the Urban-Brookings Tax Policy Center. “My sense is he’s got something in those tax returns that doesn’t look good.”

He may have less income than believed, potentially undermining his standing as a good businessman. He may be avoiding taxes by shifting profits overseas – a practice he denounces. But whatever other reasons he has, there’s a good chance that his returns would show that he pays a lower tax rate than the typical working American.

The middle 20 percent of Americans pay about 14 percent of their income in all federal taxes. To them, Trump’s zero-percent rate could be a cause of some resentment.

The typical wage slave can’t donate his golf course for a conservation easement, or take a low salary so that his income is taxed at the capital-gains rate of 15 percent rather than the regular rate of 39 percent. The average worker can’t skirt rules on loss limitation by arguing that he’s a material participant and not a passive investor, or use “flow-throughs” to convert ordinary income into capital gains. “Real estate is notorious for having a lot of different deductions,” said Steven Rosenthal, a longtime tax lawyer now with Urban-Brookings.

The only limitation Trump has faced is how creative and aggressive he wants to be – a likely explanation for his wish to keep his returns hidden.

Dana Milbank is a columnist for Washington Post Writers Group.