How Trump Brought Down his Own Casino Empire

Donald Trump was, perhaps, the strangest United States President to have ever existed. By 2016, much of America had grown weary of Washington's puppets, clearing him to put the pedal to the metal down lethargy lane. Wanting anything other than a politician, The United States had made way for a caricature of a business tycoon.

Polarity was his politics. Knowing full well he need only sound and act like the stark opposite of a career policy maker, he spoke with even less restraint than today's teenagers. How did he get away with it? Surprisingly, by doing a decent job. While he warred with a perplexed press he brokered peace in the Middle East. While the rest of the world's leaders threw stones at him (from within their glass houses), he sold them oil - as Head of an energy independent State. Gas was dirt cheap, purchasing power had risen. Everything was going up, even against the laws of physics.

Then COVID struck. The rules changed. Trump's precious economy, his winning ticket, was torn up in the shredder of crippling regulations. Though, ironically, it was his hesitancy to adhere to them that cost him his second term. Joe Biden's unwavering critique, coupled with a promise to end the pandemic, won him favour with voters who had rebuked legacy lawmakers just four years prior. But Trump, rendered a caricature with a story to tell, did not go down easy.

His loss was loud, and if the events of January 6th hadn't tarnished his legacy... that's because he'd already fallen from grace.

The $10 Billion Man

Did you know, for example, that the 45th US president is responsible for sending SIX companies under his stewardship into bankruptcy?

Coinciding with the US recession, the early 1990s saw a trio of Trump-run companies subjected to Chapter 11 bankruptcy, with a further three following suit over the proceeding years. This despite amassing a net worth reputed to be in the region of $10 billion.

Paradoxically, Trump has never filed for bankruptcy himself, proudly declaring: "I have never gone bankrupt." So how was Trump miraculously able to ward off personal bankruptcy while his own companies crumbled around him? An interview given by the man himself in 2015 holds a big clue:

"I have used the laws of this country just like the greatest people that you read about every day in business have used the laws of this country, the chapter laws, to do a great job for my company, my employees, myself and my family."

Catalogue of Failings

Trump was able to manoeuvre around bankruptcy through the use of underhand tactics that transferred accountability to investors, creditors and shareholders - to anyone but himself, essentially.

In other words, the burden of Trump's failures fell to others who had "bet on his business acumen," according to a 2016 New York Times piece - enabling him to protect his own interests at all costs.

Here it's worth pointing out that Trump apparently saw himself as something of a casino mogul back in the 80s and 90s. We're not entirely sure whose advice he bought, but it definitely wasn't ours.

Over those two decades, the bankruptcy courts became an all-too-familiar second home for Trump - seemingly the only place more accustomed to his bright visage than the tanning salon.

Of Trump's six bankruptcy appearances, four were concerned with the brick-and-mortar casino sector, as alluded to. All the more mystifying since rival businesses were known to be flourishing around these times - further tarnishing Trump's unenviable track record.

Let's examine a handful of Trump-owned casino businesses that have fallen victim to his entrepreneurial ineptitude.


Trump Taj Mahal (1991)

Borrowing inspiration from India's mesmerising mausoleum, Trump's most ambitious project to date took the shape of Taj Mahal Casino Resort that came at an eye-watering cost of $1.2 billion.

Upon opening, it was estimated the resort would need to recoup $1.3 million in daily earnings just to honour its interest payments - a feat no casino before had ever achieved. In hindsight, the then world's largest casino was doomed from the outset, with debts reaching as high as $825 million at one point. Even the world's luckiest gambler would struggle to make back those fees.

Laughingly branded the 'eighth wonder of the world' by Trump himself, it duly took less than a year for the resort to seek protection from Chapter 11 citing construction costs that dwarfed what little revenue was incoming.

Trump was left with half his original stake following the debacle and made to reluctantly relinquish ownership of his Trump Shuttle airline plus his treasured yacht. Bondholders suffered a similarly dim fate, each left to rue their ill-advised investment.

As for the casino itself, it resumed trading for a brief period before finally shutting its doors one last time.

Trump Plaza Casino (1992)

Still in the throes of recession, the casino scrapheap grew larger again in 1992 with the arrival of Trump Plaza Casino, which had narrowly fended off bankruptcy just 12 months prior.

Situated one mile from sibling casino the Trump Taj Mahal, the casino shone like a beacon on the famous Atlantic City Boardwalk, complete with 612 rooms built over 39 floors.

But like everything else Trump touched in casino land, its sheen would soon wear off.

In an effort to salvage the failing business, restructuring efforts in March that year saw $250 million worth of debt exchanged for $200 million of bonds carrying lower interest rates, along with $100 million worth of stock.

While those transactions succeeded in injecting fresh vigour into the project, its 30-year-long trading tenure ceased abruptly in September 2014, rendering around 1,000 employees jobless. And just two months ago the Trump Plaza Hotel and Casino shuttered up for good following a controlled implosion - another entry in Trump's litany of business disasters.


Trump Plaza Hotel (1992)

Not content with consigning Trump Plaza Casino to ruin, its founder swiftly turned his attentions to yet another ill-fated hotel venture that would bear his name.

Located on premium Manhattan real estate, Trump Plaza Hotel had racked up debts totalling an eye-watering $550 million by the time debtors came calling.

Parting with a 49% interest in Trump Plaza Hotel meant its owner forfeited any controlling stake in the venture, along with his hands-on role in day-to-day operations. Besides his diminished stake, however, Trump had managed to emerge relatively unscathed from the disaster - and not for the first time.

No prizes for guessing why Trump Plaza Hotel descended into bankruptcy... "Unable to honour debt service payments," according to official records. Trump had unscrupulously once again played his own Trump Card - and won - leaving others to survey the aftermath of yet another mangled business venture starring Trump as puppet-master.

Notably, the hotel continues to trade today, albeit under different, and presumably far more competent, management.

Doomed to Fail

Throughout his decades-long foray into the glamourous casino arena, Donald Trump left a veritable trail of devastation in his wake - the effects of which are still being felt today. Some of those entangled in his web of deceit remain understandably bitter over the whole sorry saga.

"When he went bankrupt, he not only cost bondholders money, but he hurt a lot of small businesses that helped him construct the Taj Mahal," H. Steven Norton, former Casino Executive at Resorts International, said.

Countless others share Norton's pain. Beth Rosser, whose father's company was took to the brink of collapse by Trump, twisted the knife some more: "Trump crawled his way to the top on the back of little guys, one of them being my father. He had no regard for thousands of men and women who worked on those projects."

A common thread runs throughout this article: Trump's single-handed destruction of honest livelihoods to the multi-billion dollar benefit of himself and his family.

A man of his times, Trump is the symbol of a new American pastime: failing upwards.