A Guide to Donald Trump’s Business Career


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A Guide to Donald Trump’s Business Career

Donald Trump’s business career has been a veritable rollercoaster ride of his own making – as with most Trump-ian pursuits.

Let’s take a look at Trump’s biggest successes and failures in business.

Successful Business Ventures

Grand Hyatt Hotel
Turned deteriorating Commodore Hotel into lavish Manhattan cornerstone.

Wollman Rink
Renovated for Mayor Koch $350k under budget.

Trump Place
Initially intended to become “Television City.” Following years of negotiation, residential complex opened on Upper West Side.

Trump Tower
Iconic skyscraper stands on 5th Ave., just below Central Park. Labor lawsuit concerning controversial construction settled in 1999.

40 Wall Street
Bought for $1MM, renovated for $35MM, worth $500MM.

Trump International Tower Chicago
2nd tallest hotel in Chicago was named best large city hotel in North America in 2010.

Trump Model Management
One of Manhattan elite boutique model agencies. Currently the defendant in multiple lawsuits.

The Apprentice
Successful show spawned “Celebrity Apprentice” spinoff. NBC cut ties with Trump in 2015, but show expected to continue.

Failed Business Ventures

Trump Vodka
5 years (2006-2011)
“Trump and Tonic” never became America’s most popular cocktail, as Trump forecast.

Trump: The Game
2 years (1989-1990); (2005)
Monopoly-styled board game discontinued, revived as tie-in to “The Apprentice,” and discontinued again.

Trump Airlines
4 years (1988-1992)
Bought for $365 million as Eastern Air Shuttle, Trump planned to turn blue-collar airline into luxury fleet. It never turned a profit.

Trump Entertainment Resorts
20 years (1995-2015)
Casino entity has filed for bankruptcy 4 times. Trump resigned from board in 2009 but maintains 28% stock share.

1 year (2006-2007)
Search engine for luxury travel deals included private jets and 120% price guarantee.

Trump Magazine
1.5 years (2007-2008)
High-end lifestyle magazine saw initial success “cashing in on the booming advertising market for yachts.”

Trump Steaks
5 years (2007-c.2012?)
Unknown when company bowed, but possibly in 2012 after Vegas chain shut down following 51 health code violations.

Trump University
6 years (2005-2011)
Un-accredited, for-profit school has been sued twice, most recently for $40 million by NY Attorney General.

Trump Ice
15 years (c.1995-2010)
First served at his casinos, Trump claimed “it was so good that people wanted to buy cases of it!”

Trump Mortgage
1.5 years (2006-2007)
Predicted by his son to be #1 US home-loan lender. Shuttered amidst housing crash and discovery that top executive had worked on Wall Street for just 6 days.

New Jersey Generals
2 years (1983-1985)
Bought USFL team, sold away, and reacquired. Team and league ended following year.

That’s a 42% success rate.

Which is an excellent baseball batting average.

His failures have an average lifespan of 4.6 years, excluding outliers.

With a median of 4 years.

So how much is Trump really worth?

Trump: over $10B
Forbes: $4B
Bloomberg: $2.9B
North Fork Bank (2005): $1.2B
Wall Street Journal: over $1.5B
Deutsche Bank: $788MM
New York Times (2005): $150-$250MM

It’s a bit muddied.

500 entities in which he is a trustee, president, chairman or member
391 of which bear the Trump name, which he values at $3,320,020,000

Stock portfolio:

But this year alone he’s lost more than a dozen multi-million dollar deals.

Farouk Systems
PVH Corp.
Jose Andreas
Geoffrey Zakarian
Federal Aviation Administration
5 Rabbit Cerveceria
Studio Ora TV
City of New York

It’s also not entirely clear Trump’s fortune was made by him at all.

1974: Inherited $40MM

$40MM reinvested dividends 1974-2015 S&P 500 Index:

$200MM (1982 net worth) reinvested dividends 1982-2014 S&P 500 Index:

Depending on how much you think he’s currently worth, Trump might’ve made more money by just riding out the S&P Index.

It’s possible he’s even lost a few billion. Though, to be clear, we’re not saying that for certain. (We’re loathe to lawsuits, and Trump’s had a few.)

Either way, it’s a moot point, because one thing is for certain:

Trump still has more money than you.