Will massive tax avoidance hurt Trump in red counties?

Taxes on family owned corporations are complex, so we need to be careful before accusing the president of tax evasion or fraud. But some telling truths have emerged from the revelations uncovered by the New York Times in Donald Trump’s tax returns from 2000 to 2018:

  • He has been a very successful entertainer, earning $427 million from starring in “The Apprentice.” The Times summarized: “His genius, it turns out, wasn’t running a company. It was making himself famous — Trump-scale famous – and monetizing that fame.”
  • He is a total loser as a business executive. Every business he owned lost money. He lost money in 11 of the 18 years in the tax returns. He blew through the big money from the TV show, partly to live high and to invest in golf courses. The golf courses, where he spends a lot of time, bleed money.
  • Ergo, he is far from a magical deal maker he purports to be. He is a sucker for bad deals. He used his father’s money to buy casinos on the east coast, and they went bust.
  • His tax maneuvers may or may not be legal, but he made maximum use of loopholes to avoid federal taxes for two decades. Legal or not, his monumental tax avoidance will not sit well with taxpayers/voters who consider it patriotic to pay their fair share of U.S. taxes. He may get some points back for forgoing his salary.
  • He loves debt. Every businessperson tries to avoid personal guarantees of corporate debt. But Trump has signed up to personally backstop $427 million of corporate debt, with $300 million coming due in four years. Where is he going to get that repayment money? He has burned so many lenders that banks are a dry hole. He could sell his best properties. We don’t know his total debt or the valuation of his properties.
  • He will be vulnerable to what’s called “vulture lenders.” He needs a bailout, possibly a bankruptcy reorganization or a new TV gig. His cavalier approach to debt reflects in the soaring U.S. deficit and national debt during his four years, even before the COVID bailouts.
  • The leaker of what Trump calls fake news about his returns remains secret. Trump will try to nail the source of his returns before the election Nov. 3. He will try to blame Joe Biden. But that tactic will not change the business and tax facts that were revealed. So far, Trump has not challenged the substance of the Times’ reports.

There will be more revelations about Trump family finances to come over the six weeks to election day. Their effect on the Nov. 3 outcome is unknown. Most voters have already made up their minds, and many ballots have already been mailed.

Yet there are still undecided voters, even in Washington, Ozaukee and Waukesha counties, among the reddest and most committed in country. You would have to think that the Trump’s massive business losses, the resulting coverup and the whopping tax avoidance would be a tipping factor for some of them.

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