The whole "savvy business people game their taxes" thing doesn't play when there's outright fraud
There are at least three disturbing cases of out-and-out tax fraud suggested (if not definitively proven) in the NY Times report:
1) Trump claimed to have "abandoned" his Atlantic City casino businesses in order to book them as a loss that he then subsequently used to avoid income taxes. But he collected payouts from those properties subsequent to have declared them abandoned. He would therefore be able to report no more than $3000 a year in losses from those properties. The matter is currently with the IRS and the Congressional panel that makes judgments on these issues, but if found that he collected even one red cent from the businesses subsequent to have declared them abandoned, he stands to owe $72 million plus interest (estimated $100 million). Declaring assets to be abandoned for the purposes of writing off losses, then collecting revenue from them is not "gaming the system." It's out and out fraud.
2) He double paid his family and otherwise used supposed consulting fees for write offs when there was no consulting. The Times article is pretty definitive on this, even matching payouts to the dollar in consulting fees to payments received by Ivanka Trump. She was working for the Trump Org and should have been receiving salary, but was also presumably received these consulting fees. Nice gig if you can get it, but that's double booking the same work where any of us come from, with the advantage of adding a business write-off line for the Trump Org. The Times also documents several projects where consultants are listed as paid on the tax form, but nobody involved in the project remembers any consultants, and several participants scoff at the idea that there were consultants. These write-offs are outright fraudulent, not savvy gaming of the tax system. You don't get to invent consultants or double book expenses even with our fucked up tax system.
3) The treatment of the Seven Springs estate - which Trump has claimed is "land conservation" for charity as well as an investment property, though the Trumps have always treated it as a personal home, and are even on record saying that. It's clownish misstatement. They've reaped over $20 million in write-offs from this mislabeling. It's fraud.
There are more cases in the Times article, but these are three that popped out at me. None of this is "savvy" use of the tax system. They're outright lies. People have gone to federal prison for less than this.
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