Donald Trump’s most perilous financial circumstances are ahead of him.
The long running audit of the Trump Organization’s federal returns, including a $72.9 million refund, remains unresolved.
Depending on the final decision of the Internal Revenue Service, a reversal of the large refund, plus interest and potential penalties, could result in the President and his businesses owing the federal government over $100 million.
The Trump Organization also faces looming debt payments on Trump properties that will undoubtedly place financial pressure on Trump and his businesses.
The New York Times reports that Trump appears to be personally on the hook for over $421 million of loans made by third-parties to Trump entities.
There is also a $100 million mortgage due on the iconic Trump Tower.
With massive debts coming due, and the prospect of a substantial federal tax bill looming, Trump may once again be facing financial bankruptcy.
If Trump should win the reelection in November, some of his major bills will come due while he is in office, also raising the prospect of a financially beleaguered President distracted by his own potentially ruinous finances.
Trump has bragged about how well his businesses have fared in bankruptcy.
And in fact, no major U.S. company has filed for Chapter 11 more than Trump’s casino empire in the last 30 years.
“I have used the laws of this country … the [bankruptcy] chapter laws, to do a great job for my company, for myself, for my employees, for my family,” he said in 2016, adding that ‘many other’ top businesses did the same thing.
But the facts don’t back that comment up.
Despite high profile examples, including General Motors (GM), Lehman Brothers and most of the nation’s major airlines, fewer than 20% of public companies with assets of $1 billion or more have filed for bankruptcy in the last 30 years, according to data from Bankruptcy.com and S&P Capital IQ.
Trump has has filed four business bankruptcies, which Bankruptcy.com says makes Trump the top filer in recent decades.
All of them were centered around casinos he used to own in Atlantic City.
They were all Chapter 11 restructurings, which lets a company stay in business while shedding debt it owes to banks, employees and suppliers.
Here’s a look at Trump’s bankruptcy track record.
1. Trump Taj Mahal, 1991
Trump’s first bankruptcy filing was probably the most personally painful for him. To come up with the funds he needed, he sold a 282-foot yacht, as well as the Trump Shuttle, the airline he operated at the time that flew between Washington, D.C., New York and Boston, according to media reports at the time. He had to give up half of his ownership stake in the Trump Taj Mahal, but he did retain control of the property. His largest creditor was financier Carl Icahn, who held $400 million in bonds. Now Icahn is Trump’s pick for Treasury secretary should he be elected.
2. Trump Castle Associates, 1992
In less than a year he was back in bankruptcy court for his other Atlantic City casinos. This bankruptcy included the Trump Plaza Hotel in New York, the Trump Plaza Hotel and Casino in Atlantic City as well as the Trump Castle Casino Resort. He gave up half his interest in the New York Plaza to Citibank, but retained his stake in the casinos.
3. Trump Hotel & Casino Resorts, 2004
Trump didn’t go back to bankruptcy court again until November 2004, when he filed to shed debt at his various Atlantic City casinos and a riverboat in Indiana. It was another quick trip through bankruptcy court; the company shed $500 million in debt and emerged from bankruptcy the following May. Trump turned over majority control of the company to his bondholders but remained the largest single shareholder, and he once again kept control of the casinos.
4. Trump Entertainment Resorts, 2009
His most recent bankruptcy came in 2009, after the company missed a $53.1 million bond payment. That was pretty much the end of the road for Trump in Atlantic City. While his name remained on three casinos, he resigned from the board and gave up his remaining stake in the company.
“I had the good sense, and I’ve gotten a lot of credit in the financial pages, seven years ago I left Atlantic City before it totally cratered,” he said during the debate.
The two Atlantic City casinos that still had the Trump name filed for bankruptcy yet again in 2014. At the time Trump made sure people knew he was no longer running the company, and sued to have his name removed.