The NYT story yesterday on how Trump had hundreds of millions of dollars in loans tied to his Chicago tower was filled with fascinating detail, but there's still so much not answered, like this weirdness https://www.motherjones.com/politics/2019/09/donald-trump-has-never-explained-a-mysterious-50-million-chicago-unit-acquisition-loan-is-it-evidence-of-tax-fraud/

We first reported last fall (and @Fahrenthold and others have dug in on this as well) that Trump lists owing himself money, tied to his Chicago project. In a 2016 interview with the NYT, he said it was the result of a loan he bought from lenders: https://www.nytimes.com/2016/05/24/business/dealbook/donald-trump-relationship-bankers.html

There's a lot about that 2016 article, which in retrospect seems questionable. For example, Trump also said he had $1B cash. That's not what his personal financial disclosure showed, and he doesn't have that kind of dough now, which is a problem for him https://www.motherjones.com/politics/2020/06/donald-trump-loans-deutsche-bank/

He also says he was paying himself interest on the loan. If he is, he was not reporting it properly on his personal financial disclosure, where the LLC should've shown income earned from the interest, even if it was from himself.

Also, after searching high and low, we could find ZERO evidence for the existence of a loan that he might have purchased. He had his DB loans, which the NYT story delves into, and he had his Fortress loan. We determined, and reported, that he DID NOT buy that loan.

At the heart of this is debt forgiveness and the taxes you owe. You don't pay taxes on money you receive as a loan. It's not income. It's a loan. But if the loan is forgiven, it's not a loan, it's income. So, if you buy a loan, instead of paying it off, you can maybe avoid taxes.

As Trump described buying his loan to the NYT, it sounded plausible that maybe he was trying that tactic, known as debt parking. But if no loan was bought and he only says he is, then maybe it's a sign of tax fraud? https://www.motherjones.com/politics/2019/09/donald-trump-has-never-explained-a-mysterious-50-million-chicago-unit-acquisition-loan-is-it-evidence-of-tax-fraud/

The NYT says his tax returns show he properly reported his forgiven debt to the IRS, but still managed to avoid paying taxes on the "income", because his other losses were so great.

OK.

So, then we're back to the start... what is this loan on his personal financial disclosure?

And why did he tell the NYT it's a loan he bought?

This from @davidenrich who co-bylined the NYT story is extremely true. Four years in, even those with access to his tax returns can't make heads or tails of this. And yet, Trump is not being asked about this! https://twitter.com/davidenrich/status/1321528678065545216

Part of the problem is that this stuff is INSANELY complicated, in particular because the way people like Donald Trump (real estate developers) deal with debt is not anything like the way normal ppl do. Loan forgiveness is not uncommon. Interest-only nine-figure loans is normal.

At the debates, Trump was able to brush off questions about his debt by going on a tangent about being underlevered. Sure, he's underlevered, but does he have cash to pay off the loans he does have? And WHAT ON EARTH IS THIS CHICAGO LOAN?

He's been able to obfuscate, but also no one is asking him point blank about this stuff. How will you repay your debt? What is this Chicago loan?

The thing that really has seemed odd is why Trump ever included this loan on his personal financial disclosure. It raises a lot of questions, has no good answers... and may not be real.

Why include?