Trump's Long List of Tax Troubles

Higher taxes for thee, but not for me.

There may be a really good reason Donald Trump doesn’t want to open up his tax returns to scrutiny. If an analysis from USA TODAY is to be believed, Herr Trump’s business dealings have been steeped in over 100 different tax-related disputes or lawsuits.


Trump’s companies have been engaged in battles over taxes almost every year from the late 1980s until as recently as March, the analysis of court cases, property records, and other documents across the country shows. At least five Trump companies were issued warrants totaling more than $13,000 for late or unpaid taxes in New York state just since Trump declared his candidacy in June 2015, according to state records. This spring, as Trump flew to campaign rallies around the country aboard his trademark private jet, the state of New York filed a tax warrant to try to collect $8,578 in unpaid taxes from the Trump-owned company that owns the Boeing 757. The company has since paid that tax bill.

Trump has in the recent past, stood left-of-center, in regards to his approval of a progressive tax on wealth, even for himself. According to reports, however, what he says and what he actually does are very different.

As to his tax disputes:

They illustrate a pattern of systematically disputing tax bills, arguing for lower property assessments, and in some cases not paying taxes until the government takes additional action. At least three dozen times, Trump companies’ unpaid tax bills have forced the New York State Department of Taxation and Finance to go to local courts to get liens against his properties to try to collect overdue bills. New Jersey also had to go to court for a lien to collect a Trump company’s unpaid tax bill. Eventually, those disputes were resolved, and his companies paid some amount of taxes.


Trump’s tax troubles aren’t simply confined to New York. He has additional filings in Florida, New Jersey, and Nevada.

Trump has acknowledged that he tries to pay as little taxes as possible, and the public records across the country shed light on how he does it. In documents rarely seen by the public, Trump’s businesses regularly minimize the value of his properties for tax purposes. Publicly, including in his presidential financial disclosure report, Trump’s team declares many of those same properties are worth tens of millions of dollars more.

He’s fought tax collectors to lower the assessed values of his luxury golf courses in Briarcliff, N.Y., and Jupiter, Fla. Yet on his presidential financial disclosure report, he valued each at more than $50 million.

The gilded toad has hopped around payment of taxes to the point that there are reportedly dozens of tax warrants issued against his businesses.

In addition to the five tax warrants since his announcement, there are additional New York state tax warrants dating to the years before Trump became a candidate, including $1,580 in unpaid taxes in 2010 for Trump Mortgage, his failed mortgage venture, and $1,747 in unpaid taxes in early 2015 against Trump Entrepreneur Initiative, once known as the troubled Trump University, which was later paid.


Trump loves to brag about his ability to make the best deals, until the tax bill comes on those deals, then he tries to undercut the worth of his own property. He writes it off as part of doing business and trying to save expense.

Others would call it trying to cheat the system that the average citizens are forced to deal with.

Among some of Trump’s tax troubles:

  • Trump Mortgage owes federal taxes from 2006 and 2007 totaling more than $4,800, according to two federal tax liens filed in New York.
  • Trump’s businesses have sued the New York City Tax Commission 55 times from the mid-1990s through 2011, disputing the city’s property assessment values on everything from apartment complexes once owned by his father to his core buildings and companies.
  • Trump-related companies have become embroiled in disputes over sales taxes owed to New York state and New York City. Tax warrants on file in New York County court found that over the past 27 years, Trump entities owed about $300,000 in back taxes, which were eventually paid.
  • The battles can save Trump millions of dollars. In 2006, Trump won a ruling on his 58-story headquarters at Trump Tower in Midtown Manhattan. It was the sixth time since 1999 that his appeals against the Tax Commission reached the courtroom, records show. The net result was about a 10% reduction over 10 years on the building — worth about $3 million to Trump.

If Trump supporters don’t think this information won’t be used against him in the general, they seriously underestimate the power of the Clinton machine.





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