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Joseph Kaminski

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September 20, 2019

Donald Trump and His Failed Businesses

Like many companies led by Trump beforehand, his campaign is biting the dust in terms of generating profit. Just as his previous endeavors — Trump Taj Mahal in 1991, Trump Plaza Hotel in 1992, Trump Hotels and Casinos Resorts in 2004, and Trump Entertainment Resorts in 2009 — it seems as if his campaign is struggling through financial problems and falling short of expectations in the first quarter of the general election.

So, let me be clear, Donald is a terrible businessman. Although he claims to be left and right, most of his companies have fallen flat on their faces. So, lets look at his business flops. From terrible management to struggling markets, here’s where The Donald failed to prove “how great” of a businessman he claims to be.

Trump Airlines

Launched in 1989 and closed just shortly after its 4-year anniversary, Trump Airlines was nothing more than an attempt to turn an existing service into a Trump trademark (sounds like most of his businesses, eh?).

Trump attempted to have hourly flights between Boston, New York City, and Washington D.C. — making it an incredibly limited service. Rather than using his “billions of dollahs” to start an airline from scratch — he simply purchased an already existing company. The Eastern Air Lines Shuttle got a shitty mustard-colored paint-job and lost all success with Trump in command.

Trump: The Game

Did you know the presumptive Republican nominee had his own family board game? Well, in 1989 “Trump: The Game” was released. Basically, like every other company he’s created, it was taking something that already existed (Monopoly) and making it themed around himself. The game went out of production in literally less than a year, with around two million units floating around. You can currently buy a used version of the game — a slice of Donald Trump’s failures! –for $69 on Amazon.

Trump Steaks

Trump Steaks collapsed after only one year (for $1,000 you could get 24 greasy, lackluster burgers or 16 run-of-the-mill, tasteless steaks).


A wannabe travel search engine, also went wrong after only one year. As The Washington Post analyzed shortly after the site’s launch, it was a “vanity site” indeed.

Trump Vodka

Who could forget Trump Vodka? Launched in 2006 and closing its doors five years after its initial launch, Trump Vodka is something The Donald would want you to forget. He repeatedly lied in advertising, labeling his drink as “The World’s Finest Super Premium Vodka”. He “proudly quintuple-distilled it” in Holland from “select European wheat”. He put so much time and effort in battling companies like Grey Goose for a spot at the top shelf. And then? Nobody wanted to drink it.

Trump Mortgage

Perhaps the most embarrassing and horrifying business endeavors that Trump ever went through. Launched in 2006, the same year as his flop of a real estate search engine and his vodka failures, Trump Mortgage was supposed to be a residential and commercial real estate financing corporation. But, even someone like Donald Trump should have been able to realize the simple economics surrounding him. The market prices in 2006 were already demonstrating to the public that the bubble was about to burst. Trump told CNBC that “it’s a great time to start a mortgage company.” As Trump would almost immediately learn, it was not.

Trump Magazine

To make things even worse. The entertainment magazine for whatever the fuck “luxury enthusiasts” are, went out of business after two years of trying to target wealthy people in a recession. Get this! As soon as Trump was forced to close the doors to his mortgage company, he opened a wealthy magazine corporation. Turns out people struggling to make ends meet don’t care much for seeing people on yachts. Looks like Trump needs to understand a thing called “timing”.

Trump University

Perhaps the most controversial failure. A for-profit, non-accredited university that gave out fake business degrees, Trump University managed to survive longer than many of his other failures — six years.

If you gave the “university” $35,000, you could find yourself watching “extended infomercials”, learning to sell “non-accredited products”, and getting a degree that was literally worth, you guessed it, $0.

Trump University is currently undergoing quite a few lawsuits. It has been described by state education officials as an “illegal educational institution”. He was forced to take the name “university” off of it, but by then it was too late. Outed as a fraud and left in the dust, it shut down shortly afterwards. Although he threatens to bring it back, it’s obvious that it’s failed.

The New Jersey Generals

Did you know Donald Trump essentially purchased a team belonging to an NFL rival company (that lasted about as long as any of his own companies)? Well, from 1984 – 1985 Donald owned a football team called “The New Jersey Generals”. Basically, he was too poor to purchase an actual NFL team. So, he considered this the next best thing.

He gave up rather quickly, selling the team only to swiftly repurchase it within the same time-span. He literally had no idea what the Hell he was doing, and tried to pull the New Jersey Generals into the NFL itself. Guess how well that worked out for him? The entire league collapsed because of his poor investments and terrible goals.

Trump New Media

A video-on-demand and high-speed-internet service established in around 1998, Trump New Media was Trump’s attempt to dive into the world of internet monies. He planned to “wire his 20,000 residential apartments with high speed internet” for only $30 a month.

Honestly, this plan sounds rather “in his atmosphere” at first glance. He owns enough apartments to look into an investment plan towards completely financing them in his own accord. But, it failed. He tried to partner with Freelinq Communications, failed to compete against the competition in the boardroom, and it never took off.

The Trump Network

You can’t be an eccentric millionaire pretending to be a competent billionaire without having your very own pyramid scheme with your own name on it! It’s literally nothing more than a vitamin pyramid scheme! It was literally nothing more than a get-rich-quick scheme centered around vitamins that could “discover the difference between opportunity and success”.

Why not just watch a video about it from The Daily Show?

There are so many other companies that I could bring up in Donald’s search for success. Trump on the Ocean, a restaurant in Long Island that literally lasted four months before Hurricane Sandy scared him away. Tour de Trump — a bike race committee that continued Trump’s tradition of stealing something that already existed and putting his name on it that he was forced to sell. Trump Ice, in which Donald decided he could get away with bottling his casino water for no apparent reason whatsoever.

Are you starting to get it? This is the man people want in charge of the country because he’s “a good businessman” who “can make America great again”. Well, I hate to break it to you: but how can he make America great again if he could never make a single business of his great to begin with?

Even if he was, by some miracle, a great business man — we’ve had one successful businessman become president in the past: Herbert Hoover. If you can’t tell me what went wrong under Hoover’s administration, then you can’t tell me you know enough about politics to let Donald get elected this November.

His campaign is broke — with 40x less money than Hillary Clinton and an inability to raise money the same rate as the Democratic base. He’s being forced to fire staff members and he’s been replacing them with last-ditch efforts to help him out — including his right-hand man Corey Lewandowski. He’s “so rich”, but is being forced to pull out loans left and right and won’t just put a few million into his campaign.

He doesn’t have the cash. He doesn’t have the experience. He doesn’t have anything.

He’s an entertainer, and he’s been entertaining you all for long enough. It’s a shame that the defunct Republican Party has turned to him as someone to unite the five ring Republican circus. How on Earth can someone who couldn’t unite his own damn companies unite a political party? How on Earth can someone who’s failed time and time again find success in the first term of presidential power?

Don’t let America become Donald’s next failed business endeavor.

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