``When he filed his 2008 tax return, he declared business losses of $697 million. Tax records do not fully show which businesses generated that figure. But working with tax experts, The Times and ProPublica calculated that the Chicago worthlessness deduction could have been as high as $651 million, the value of Mr. Trump's stake in the partnership -- about $94 million he had invested and the $557 million loan balance reported on his tax returns that year.


the core of the I.R.S.'s position is that Mr. Trump's 2010 merger violated a law meant to prevent double dipping on tax-reducing losses. If done properly, the merger would have accounted for the fact that Mr. Trump had already written off the full cost of the tower's construction with his worthlessness deduction.


If the I.R.S. prevails, Mr. Trump's tax returns would look very different, especially those from 2011 to 2017. During those years, he reported $184 million in income from "The Apprentice" and agreements to license his name, along with $219 million from canceled debts. But he paid only $643,431 in income taxes thanks to huge losses on his businesses, including the Chicago tower. The revisions sought by the I.R.S. would require amending his tax returns to remove $146 million in losses and add as much as $218 million in income from condominium sales. That shift of up to $364 million could swing those years out of the red and well into positive territory, creating a tax bill that could easily exceed $100 million.

Well, of course Trump in effect generated a giant chunk of his latter-day fortune by harvesting bogus tax losses. On top of precedents such as the alleged tax dodges involved in the inheritance of his dad's estate, and the highly-questionable Seven Springs deductions, it's all likely par for the course for him. The only surprising thing is he might actually end up having to pay a big chunk of it back (apparently, only about half of the total value, since the IRS didn't react until tax year 2010, when it would have needed to go all the ways back to tax year 2008 to question the full breadth of the maneuver).

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