NEW YORK (TheStreet) -- Donald Trump has never declared bankruptcy, but his businesses have -- four times.
The real estate mogul, television star and Republican presidential frontrunner filed for corporate bankruptcy in 1991, 1992, 2004 and 2009. Three of the cases were related to his casino and hotel properties in Atlantic City, N.J.
And even though more than six years have passed since Trump had his last run-in with Chapter 11, it remains a touchy subject. Trump was quick to clarify at the Republican presidential debate hosted by Fox News in August that he had never filed for personal bankruptcy. Instead, he cast his moves as part of his solid business acumen.
"Out of hundreds of deals -- hundreds -- on four occasions, I've taken advantage of the laws of this country, like other people," he said. "The difference is, when somebody else uses those laws, nobody writes about it. When I use it, it's like, 'Oh, Trump, Trump, Trump.' The fact is, I built a net worth of more than $10 billion. I have a great, great company. I employ thousands of people. And I'm very proud of the job I did."
A Trump spokesman said many of the filings occurred when Trump was no longer involved in the businesses, blaming them on the declining casino market in Atlantic City. "It's not fair to judge anyone of his success, and the empire that he's built, on a particular investment without also looking at all of the great success he's had," he said.
Overall, the Donald is no stranger to business maneuvers that, depending on whom you ask, can appear either particularly savvy or ripe for criticism. His history with bankruptcy is no exception-- take a look at the four cases below:
1991, Trump Taj Mahal
Trump's first corporate bankruptcy, for the Trump Taj Mahal, was the one that stung the most. It was also the only time at which his personal finances were at stake.
Trump first got his hands on the property in 1988 as part of a deal involving media mogul Merv Griffin. Trump ceded his controlling interest of Atlantic City hotel-casino company Resorts International Inc. to Griffin in exchange for ownership of the Taj Mahal. The casino opened in 1990 to enormous fanfare, including an appearance by pop star Michael Jackson, who Trump called his friend and a "tremendous talent" (you can see a video of the pair's casino walkthrough here).
Just days after opening its doors, the Taj Mahal hit a glitch: Its slot machines came to a halt, as money was coming in too fast for cashiers to keep up. The Trump organization also shook up the casino's executive team.
By 1991, Trump's corporation had filed for Chapter 11 bankruptcy protection from creditors of the Taj Mahal Casino Resort, which had cost $1 billion to build. Unable to pay the high interest rates on the junk bonds used to finance the resort's construction, Trump was forced to surrender half of his ownership interests in the property to bondholders in exchange for their acceptance of lower interest rates.
The only hiccup in the expedited six-week restructuring process came from a company called Dixie-Narco, which had supplied 1,350 bill-changing machines to the Taj Mahal, according to a New York Times report. Dixie-Narco said Trump had improperly solicited bondholders by saying its $6 million claim was worthless. The two sides reached a settlement for $2.4 million, with the Taj Mahal agreeing to give back 500 of the machines.
The Times also reported that Trump faced about $900 million in personal liabilities, which he reduced to about $550 million by the end of the year. The ordeal led to the sale of his Trump Princess Yacht and Trump Shuttle airline.
It provided an important lesson as well. Ted Connolly, a Boston Bankruptcy attorney who studied Trump for his book The Road Out of Debt: Bankruptcy and Other Solutions to Your Financial Problems, told TheStreet in an August interview that the first bankruptcy was a learning experience for Trump.
"The first business bankruptcy, he had a lot of personal liabilities, guarantees on the business debt, which would have wiped him out," Connolly said. "What he did was leverage the amount of business debt to negotiate away his personal liability. And from that, he learned not to put his personal wealth at risk anymore. And so in the next three, he didn't have any personal guarantees."
Through the ordeal was bruising for Trump, one person involved in the case said his brand and persona helped him to retain more equity than he might have otherwise. And in true Trump fashion, he denied being too concerned about the issue anyway.
"You'll never see me sitting in the corner sucking my thumb," Trump told BusinessWeek at the time. "The name Trump will be hotter than ever."