For legendary tycoons, Donald Trump tops the list, but how many times has Donald Trump filed for bankruptcy? The 90’s recession wasn’t picky about who it affected. Donald Trump felt the pinch as well. His decision to use high interest bonds to finance the assembly of the Taj Mahal casino caused life to get very stressful for the tycoon.
In 1991, unable to pay a $3.5 billion loan, he declared business bankruptcy. He also came close to filing personal ruin. At the time, his personal debt was estimated to be around $900 million. Due to the bankruptcy, banks and bondholders lost millions. They came to a compromise with Donald Trump. The banks gave him lower interest rates and a longer time frame to repay the debt and Donald Trump gave the investors half the ownership of the Taj Mahal. In mere months the casino was back in business.
Not even a year later, Trump Plaza Hotel folded and Donald had to declare bankruptcy. Again, he worked out a deal where he’d give up 49 percent of the hotel to Citibank and the other lenders and he’d get more time to pay the loan back. It took him two years to repay most of his debt with many sacrifices. He had to give up the Trump Shuttle.
The bankruptcy saga didn’t stop there. In 2004, Donald filed for bankruptcy protection and restructured his debt. He reduced his ownership of Trump Hotels & Casino Resorts to 27 percent and gave bondholders stocks to help lower his debt and then stepped down as CEO. In 2005, things settled down and Trump Hotels & Casino Resorts came out of bankruptcy with a new name, Trump Entertainment Resort Holdings.
Unfortunately the reemergence didn’t last long. On February 17th 2009, Donald Trump filed for Chapter 11 bankruptcy with a debt ratio of $50 million in assets to his $500 million in debt. This filing made the third bankruptcy for Trump Enterprises.