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Why did Trump's debt-for-equity swap allow him to avoid a big tax bill?

I understand that Trump avoided a huge tax bill from debt forgiveness by a "partnership equity-for-debt swap". But why did that work? And why, as the New York Times said, would it not have mattered if the equity was worthless? If it was a swap, with whom? I would expect it to be with the creditors. But I would think that if you owed $40 million to someone and gave them $30 million worth of stock in exchange, you'd still have $10 million of debt forgiveness to pay taxes on -- or if the stock was worthless, $40 million; why wasn't that true?

https://www.msn.com/en-au/news/world/donald-trump-...

Update:

<Edit> Why wasn't the scenario I envisioned below what actually happened?

1 Answer

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  • 5 years ago

    You can babble on all you want, but he took a perfectly legal capital gains loss deduction. If you have been led to believe this was something wrong or unethical, you have been mislead.

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