Since 2009, it's been off Trump's books, according to investigators, because he had taken a tax position that the Chicago tower was worthless.
"Donald Trump falsely inflated his net worth by billions of dollars to unjustly enrich himself, and to cheat the system, thereby cheating all of us," said New York Attorney General Letitia James.
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According to a 222-page complaint, Trump was using the "worthless property" as collateral for bank loans to buy other things.
RELATED: New York AG Letitia James files $250M lawsuit against Trump, his company
And Trump's tower in Chicago was a sizable piece of an alleged scheme to pad his net worth by billions, according to the attorney general, involving his golf courses and the now infamous Trump retreat in Palm Beach, Florida.
"She had examples, including former President Trump's apartment in Trump Tower, having been inflated in size. Mar-a-Lago having its evaluation inflated," said ABC News Contributor Kate Shaw.
The alleged fraud is labeled a family affair, with three Trump children accused: Don Jr., Ivanka and Eric. Repeatedly, and persistently, they are accused of manipulating asset values to induce banks to lend money to the Trump Organization.
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Authorities suggest the alleged Chicago tower fraud rolled over for years, with Trump reviews and authentication every year from 2014 to 2021.
"Claiming you have money that you do not have does not amount to the art of the deal, it's the art of the steal," said James.
There was no direct response from former president Trump regarding his alleged claim that the Chicago namesake is "worthless." He does admit to thinking this case would never be brought and calls the attorney general a racist, fraud and failure.
Her lawsuit may not be the end of it, either. Chicago legal experts tell the I-Team that Trump's conduct in the civil suit is also a federal crime.
New York state officials have now asked U.S. prosecutors and the IRS to launch criminal cases.