1991, Trump’s Taj Mahal in Atlantic City

This is the one where The Donald’s fortune was actually in any danger. After financing much of the construction of the casino with junk bonds, the luxe facility was in debt, and so was he. (Exactly how much is up for debate; the Times pegged his personal liabilities at $900 million.) In order to escape potential doom, Trump’s corporation filed for Chapter 11 bankruptcy, which allowed him to reorganize the debt while the casino remained open. The real-estate tycoon ended up taking a substantial hit this time, as he was forced to relinquish half his stake in the casino and sell his yacht and airline to pay back loans.

1992, Trump Plaza Hotel in Atlantic City

In his second swing at bankruptcy, Trump was able to insulate himself from any real harm, for the most part. This time it was the Trump Plaza Hotel that was hemorrhaging cash, having lost over $550 million. Ever the negotiator, the entrepreneur agreed to give up a 49 percent stake in the hotel to Citibank and other lenders, according to ABC News. In exchange, he received more favorable repayment terms on the debt. The celebrity developer also managed to hold onto his C.E.O. title, even though it meant giving up his salary and any role in the day-to-day operation of the hotel.

2004, Trump Hotels and Casinos Resorts

Just over a decade later, a Trump corporation was filing for Chapter 11 yet again. With the company nearly $1.8 billion dollars in debt, the businessman was back to making deals, this time agreeing to reduce his stake in the company to about 25 percent in exchange for lower interest rates and a new loan, the Associated Press reported at the time. The move meant that Trump surrendered much of his control in the company, but considering what had been going on under his watch, that was probably a good thing. (Time magazine claims Trump was also forced to pump $72 million of his own money into the company to keep it going.)

2009, Trump Entertainment Resorts

In his most recent dalliance with bankruptcy, Trump’s company declared Chapter 11 after missing a $53.1 million bond interest payment. Trump and the rest of the board of directors could not reach an agreement over whether or not to file for bankruptcy, resulting in his resignation as head of the board, Reuters reported at the time. The move also saw his stake in the company reduced even further on what Trump called a now “worthless” investment that he assured was less than a percent of his net worth.

So, it’s hard to deny that Trump’s personal finances are in great shape (although maybe not quite as good as he thinks), but his corporate track record is a little more . . . mixed. And that brand, which he’s assiduously attached to his projects, has occasionally come back to haunt him. Although he no longer has any involvement with the casino, Trump’s Taj Mahal filed for bankruptcy again in September of last year—leaving thousands of jobs to disappear into the coastal New Jersey air. The Donald’s reaction? He immediately reminded everyone, while self-congratulating his foresight, that he had pulled out of both the casino and Atlantic City years ago.

Smart!