23. Bankruptcy
In 2009, Donald Trump’s company, Trump Entertainment Resorts, files for bankruptcy, the sixth such move, all pertaining to his casino hotel ventures beginning in 1991 with the $1.2 billion Taj Mahal. It was followed in 1992 with The Trump Castle Hotel and Casino, The Trump Plaza Casino, and the Trump Plaza Hotel.
In 2004, Trump Hotel & Casino Resorts also filed for bankruptcy in a move to restructure its $1.8 billion debt. It emerged from bankruptcy in less than a year and started with a new name: Trump Entertainment Resorts, which again went bankrupt 4 years later, prompting Donald’s resignation as chairman and losing majority of his stake in the company, leaving him with only 10% ownership.
