Furthermore, Trump's business ventures have experienced significant financial losses, including multiple casino and hotel bankruptcies, the collapse of his New Jersey Generals football team, and the closure of Trump University. He and his businesses have been involved in over 4,000 legal actions, including six business bankruptcies. In 2016, it was revealed that Trump claimed a loss of $916 million on his 1995 tax returns. Additionally, an IRS investigation questioned the deductions claimed by Trump on his 2008 tax return regarding the Trump International Hotel and Tower (Chicago), potentially leading to a tax bill of over $100 million, plus interest and penalties, according to the New York Times and ProPublica.

This is just the tip of the iceberg, the larger portion is underwater