How Does Trump Repeatedly File for Bankruptcy and Still Stay on Top?

How Does Trump Repeatedly File for Bankruptcy and Still Stay on Top?

by Monica Sanders, October 2009

Donald Trump has become infamous for telling business mogul wannabes "You're fired!" every week on primetime television. Yet, after Trump's casino operations filed bankruptcy for the second time this past November, many have wondered if it isn't time for board members to give Trump a pink slip. Despite the company failings, Trump will remain as chairman and CEO and continue to collect a $2 million dollar paycheck. does a CEO decide to file for bankruptcy twice and still come out at the top of the heap?

No Personal Involvement

First, Trump doesn't get personally involved. He knows how to protect his personal finances. In both instances, Trump's corporations have filed for bankruptcy; Trump personally has not. Hence, when his casino fell into about a billion dollars in debt, the corporation filed for Chapter 11 bankruptcy. Trump only made the decision to do so once he had spoken to his banks and bondholders. But, by filing, he gave his business the opportunity to regroup and reduce his business debt. It didn't hurt however that it would also reduce his personal debt, as Trump is likely the one every creditor would look to if the Taj Mahal couldn't pay up. So, in fact, Trump avoided potential lawsuits from credits and he may have also avoided personal bankruptcy by keeping his own bank account insulated.

Trump, it appeared, had triumphed. His company had dire financial problems but seemed to rise just as quickly from those bankruptcy ashes. Just three years later, he combined the hotels into the publicly held Trump Hotels and Casino Resorts.

For several years, the new company enjoyed double digit stock prices. His personal fortune in turn also skyrocketed. And the man who came close to losing it all leapt onto Forbes' most wealthy list.

Yet, Trump's public company would eventually fall...again. Within a few years of soaring high prices, the company stock had fallen into single digits. The one-time powerhouse company remained profitless and struggled just to pay the interest on the $2 billion debt. Trump claimed that the properties were unable to make the improvements necessary for keeping up with its flashier competitors. These financial troubles led to Trump's second trip into filing bankruptcy.

Win-Win Business Deals

It's in this second bankruptcy that Trump demonstrated the other quality that helps him stay on top. He knows how to create a win-win situation. This past November, Donald Trump filed for Chapter 11 a second time. Again, Trump asked to be able to restructure his company's debt and overhaul its aging casinos. Under the voluntary bankruptcy filing, Trump Atlantic City Associates, which is 99 percent owned by Trump Hotels & Casino Resorts Inc., listed $1.3 billion in debt and $1.5 million in assets.

But this time around the Donald proposed that reorganizing the company would provide him the cash to upgrade his properties. By making these changes, he could help keep the casinos competitive. The second benefit: bondholders would receive stock in exchange for forgiving the debt owed. In other words, it would increase their ownership of the company by roughly two-thirds.

The chances of making the money back and even a bit of profit will dramatically increase when the casino emerges from the reorganization. Why? Well, vendors will be paid.

But best of all, Trump got to keep his job (and his rather hefty salary). If all goes as planned, Trump's Atlantic City properties will be able to actually turn a profit and even potentially expand into new markets like Las Vegas.

At the end of the day, Donald Trump will not only come out on top, he may well come out in the green.

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