Since 2010, per a new report, Trump has had an estimated $287 million in debt forgiven. The majority of that amount was in connection with a development for a Chicago skyscraper.

The debt and related maneuvering is detailed in a new report from the New York Times, which revealed on Tuesday after obtaining tax records that this latest example of Trumpism in the business sector began with the family's intention of using the Trump International Hotel & Tower in Chicago as a sign the company had become a key player in matters of luxury real estate.  

However, that aim didn't exactly pan out, ultimately resulting in what Times reporters described as another "case study in doing business the Trump way." Initially, according to the report, Trump tried to simply walk away from the debts when the Chicago development hit snags related to slow construction time and vacant retail space. From there, Trump was given years of additional time to make good on the debts from major banks and hedge funds. At one point, he sued the biggest lender and still managed to get another $99 million in loaned funds. 

Notably, the debts in question are now part of a larger New York attorney general investigation. 

In a statement, the Trump Organization's chief legal officer Alan Garten claimed that all taxes connected to the forgiven debts had been paid. As for the nature of the deals themselves, Garten called them "arm's length transactions" that were agreed upon in the wake of the 2008 financial crisis.

Trump has also responded to the latest Times story from reporters David Enrich, Russ Buettner, Mike McIntire, and Susanne Craig. In a tweet shared Wednesday, the failed steak salesman and notorious pandemic denier posited that such dealings made him a "smart guy rather than a bad guy."