Here is some facts:
Trump has never filed for
personal bankruptcy, but his hotel and casino businesses have been declared bankrupt six times between 1991 and 2009 in order to re-negotiate debt with banks and owners of stock and bonds.
[169][170] Because the businesses used
Chapter 11 bankruptcy, they were allowed to operate while negotiations proceeded. Trump was quoted by
Newsweek in 2011 saying, "I do play with the bankruptcy laws – they're very good for me" as a tool for trimming debt.
[171][172] The six bankruptcies were the result of over-leveraged hotel and casino businesses in Atlantic City and New York:
Trump Taj Mahal (1991),
Trump Plaza Hotel and Casino (1992),
Plaza Hotel (1992),
Trump Castle Hotel and Casino (1992), Trump Hotels and Casino Resorts (2004), and
Trump Entertainment Resorts (2009)
Everyone thinks that Bankrupt is a dirty word, but this was in fact a smart business move whenever they had to do it. So I don't see it as him being a bad business person. Just someone who knows where the loop holes are.