#1) Trump Taj Mahal (1991): The Trump Taj Mahal

#1) Trump Taj Mahal (1991): The Trump Taj Mahal casino in Atlantic City opened in 1990, with Trump financing the completion of its construction with $675 million in junk bonds at 14% interest. By the following year the casino itself was in debt to the tune of $3 billion, while Trump himself owed some $900 million in personal liabilities.

In order to keep the Taj Mahal afloat, Trump struck a deal with his lenders in which he gave up half his ownership share and equity in the casino, sold his Trump Shuttle airline and his Trump Princess 220-foot yacht, and agreed to a bank-set limit on his personal spending in exchange for a lower interest rate and additional time to make his loan payments.

#2 and #3) Trump's Castle and Trump Plaza Casinos (1992): Less than a year after the Taj Mahal bankruptcy Trump filed for Chapter 11 protection again for two more Atlantic City hotel-casinos, the Trump Plaza and Trump's Castle, over their inability to make principal and interest payments on bonds. The Plaza ($550 million in debt) and the Castle ($338 million in debt) were competing against each other, as well as against the Taj Mahal, and Trump gave up a 50% share in exchange for more favorable terms on the debts.

#4) Trump Plaza Hotel (1992): Donald Trump filed for bankruptcy protection a third time in 1992 over the Trump Plaza Hotel on New York's famous Fifth Avenue, overlooking Central Park in midtown Manhattan. Once again, Trump gave up a 49% stake in the property to secure more favorable terms from lenders on the luxury hotel's debt of more than $550 million.

#5) Trump Hotels and Casinos Resorts (2004): In 1995, Donald Trump established Trump Hotels and Casino Resorts as a publicly traded company, an entity that eventually consolidated his three Atlantic City casinos (Trump Taj Mahal, Trump Castle, and Trump Plaza), along with other properties, under one company. In 2004, Trump sought Chapter 11 bankruptcy protection for the company, with filings listing about $1.8 billion in debt. Yet again, Trump's ownership in the business was reduced, from 47% to 27%, in order to obtain more favorable terms from lenders.

#6) Trump Entertainment Resorts (2009): After its 2004 bankruptcy, Trump Hotels and Casino Resorts was renamed Trump Entertainment Resorts (TER), and that latter entity went Chapter 11 in 2009 with a debt of $1.2 billion. Trump fought with his board of directors over how to restructure the company and ended up reducing his ownership share of the business once again (to 10%) and resigning as chairman of the board.

Sold off the former Trump's Castle (by then renamed the Trump Marina) to Landry's in 2011, who rebranded it as the Golden Nugget Atlantic City. In 2014, Trump filed a lawsuit to bar the continued use of his name on TER's remaining Atlantic City casinos, the Trump Plaza and the Trump Taj Mahal, holding that "the license entities have allowed the casino properties t

Other Trump Business Failures
As well, Donald Trump has undertaken a number of business projects that ultimately failed (or failed to live up to his lofty projections) without resulting in bankrupcties, including:

Trump Steaks
GoTrump (online travel site)
Trump Airlines
Trump Vodka
Trump Mortgage
Trump: The Game
Trump Magazine
Trump University
Trump Ice (bottled water)
The New Jersey Generals (pro football team)
Tour de Trump (bicycle race)
Trump Network (nutritional supplements)
Trumped! (syndicated radio spot)
ll, Drew and Jacob Bogage. "What Trump Didn’t Say About His Four Big Business Bankruptcies."
The Washington Post. 7 August 2015.
Just a taste of what is to come!

Loser....