In 1995, Trump declared $3.4 million in business income, $7.4 million in interest income, and close to $100,000 in income from other sources such as dividends, taxable refunds and wages. But this income was more than offset by hundreds of millions of dollars in reported losses from real estate and "the financial wreckage he left behind in the early 1990s through mismanagement of three Atlantic City casinos, his ill-fated foray into the airline business and his ill-timed purchase of the Plaza Hotel in Manhattan," according to the Times.

About 46 percent of all tax filers (individuals or households) pay no federal income taxes each year because of various exclusions. High-income tax filers make up a tiny portion of that number, but they are by far the biggest beneficiaries. More than half of the tax revenue lost to the most common tax exclusions stays in the pockets of the richest one-fifth of Americans, according to an analysis by the Congressional Budget Office.

While it's rare for high-earners to pay no federal income tax, it's not unheard of. In 2011, for instance, about 433,000 tax filers with incomes over $100,000 paid no federal income tax, according to estimates based on limited IRS data by the Tax Policy Center, a nonprofit think tank. That number includes approximately 4,000 filers with an income of $1 million or more.

The wealthy and poor households that paid no income tax in 2011 did so for drastically different reasons. Most low-income filers — those with a pretax income of $20,000 or less — who paid no tax did so because of the basic structure of our progressive tax system, which determined they made just enough to cover family expenses, or less.

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Many also benefit from the Earned Income Tax Credit, which offers a refund to low- and moderate-income workers. That cost the government about $61 billion in forgone tax revenue in 2013, according to the CBO.

By contrast, high earners who paid no tax were primarily able to do so because of a wide array of other special provisions in tax law. Roughly 1,000 of the 4,000 millionaire non-payers in 2011 did so because their income that year was locked away in individual retirement accounts not subject to federal taxes, according to Roberton Williams of the Urban Institute, one of the authors of the Tax Policy Center analysis.

At an annual cost of $137 billion annually, the tax exclusion for pension contributions was more than twice as expensive as the Earned Income Tax Credit.

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Another significant chunk of the 4,000 high-income non-filers made their money from interest on municipal bonds, which is not subject to federal income tax. Reduced tax rates on capital gains were also one of most costly federal tax provisions: $161 billion.

Calculating the cost of the 10 largest tax expenditures — the exclusions, deductions and credits allowed through the tax code — the 2013 CBO report found that the top quintile of earners were the biggest beneficiaries.

The CBO report didn't include "net operating loss" in its calculation of top tax expenditures. But as Trump shows, it can be a major boon.

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People like Trump who work in real estate can use real estate losses to offset gains or income from elsewhere, according to Williams. For real estate developers, "your business is such that you're more likely to generate losses in the short run, and [the government] is going to allow you a way of deferring your taxes while you're in a losing situation," Williams said.

But, he added, often times "these are paper losses, not real losses." The tax code allows property owners in the real estate business to claim losses from things like depreciation even if the property itself is gaining market value.

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Williams says these provisions are not necessarily problematic or harmful on their own, and that they weren't created with the intention of allowing wealthy people to avoid paying taxes indefinitely. But the complexity they add to an already-complex and massive tax code can erode people's trust in the fairness of the tax system.

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"Right now we have an extremely complex tax code that literally nobody understands," Williams said in an interview. "That's not right. The reasons that isn't right is not so much that the provisions themselves are wrong, but rather that we don't understand why we're paying what we do."

This complexity can lead to suspicion of wealthy non-taxpayers, like Trump. And it can just as easily lead to suspicion of low-income people who don't pay tax either.

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"HALF of Americans don't pay income tax despite crippling govt debt," Trump tweeted in 2012. Left unsaid was that for at least part of his career, Trump was one of them.