1. The Trump Shuttle

Flickr / Aero Icarus

Trump experienced a nosedive after taking a $245 million loan to buy Eastern Air Shuttle in 1988.

The purchase agreement guaranteed that he would acquire the planes and all the routes of the shuttle line. Trump merely painted his name on the airplanes and spruced up a few bathrooms. And to his surprise, customers didn’t line up out the door.

Trump Shuttle lasted only two years before Trump defaulted on a loan and surrendered the airline to creditors.

The thing I’m really worried about is that #airforceone will go bankrupt mid-flight like #trump shuttle did.

— The Klute 🦈🌎🇺🇸 (@the_klute) February 10, 2020

2. Trump: The Game

Flickr / Kevin Dooley

In the same year, Trump teamed up with a game design company, Milton Bradley, to develop Trump: The Game. It was expected to sell 2 million units…but ended up selling only 800,000 copies.

After discontinuing in 1990, Trump stated the lack of sales was from the game being “too complicated.”

Hasbro, in fact, rebranded the game in 2004 when Trump’s celebrity began to skyrocket from The Apprentice. However, that quickly fizzled out too.

The “Trump: The Game” ads are on YouTube and are pretty saucy.https://t.co/v0Q19G7BTp

— James “Gwen” Dallas (@AD5NL) February 11, 2020

3. Trump casinos

Source / Good Free Photos

Trump has preyed on Atlantic City for so many years it’s pretty much comedy at this point. On his Atlantic City properties, he has filed for bankruptcy three times.

Taj Mahal was the first victim in 1991. It accumulated $3 billion in debt after being in operation for only one year.

He was back in court again in 2004 for the Trump Marina, Trump Plaza and riverboat casino in Indiana properties. All three carried the burden of $1.8 billion.

It doesn’t stop there.

Trump reorganized his previous corporation after the bankruptcy and manifested Trump Entertainnment Resorts Inc. But without fail, four years later, he missed an interest payment on a $53.1 million bond forcing his company into bankruptcy. Trump finally stepped down as chairman.

Trump bankrupted casinos.

— panasonicyouth_ (@panasonicyouth_) February 6, 2020

4. Trump Magazine

Screenshot / YouTube

Trump later had the bright idea to launch a magazine in late 2007. It derived from previous publications known as Trump Style and Trump World.

He wanted to focus on the growing advertising market for high-end luxury commodities. Unfortunately for Trump, his timing was a little bit off.

The financial crisis hit, and the magazine folded by 2009.

Look, his bankruptcies have crushed small businesses and the men and women who work for them. He inherited his business, he didn’t create it. And whatever happened to Trump Airlines? How about Trump University? And then there’s Trump Magazine. A business genius he is not.

— Vic Vega (@CapitalisticPig) February 5, 2020

5. Trump Mortgage

Screenshot / YouTube

To capitalize on the “booming” housing market, Trump started talks about how it was a great time to jump into the mortgage industry in 2006.

What he forgot to mention was that the market had already begun to decline and would shortly collapse. Trump’s mortgage business fell far short from it’s projected $3 billion in sales. It did less than a third of that. Trump blamed it on the people who actually ran the company.

E.J. Ridings was called upon to be CEO of Trump’s mortgage company. Ridings was boasted as a Wall Street savant… but turned out to have just six months of experience as a stockbroker.

The company collapsed in September 2007.

Ever hear of “Trump Mortgage?” It folded in 18 months.

“….Trump Mortgage collected their $500,000 commission, but stiffed McGovern, who filed a lawsuit. In 2009, McGovern obtained a judgment of US$298,274 against Trump Mortgage.”

— THE ACCOUNTANT (@LinkedHD) February 8, 2020

6. Trump Steak

Screenshot / YouTube

For some odd reason, Trump’s bankruptcies in Atlantic City had a connection to meat. Court records showed he owed Buckhead Beef over $700,000.

Trump and Sharper Image signed a deal to sell a rebranded version known as Trump Steaks. The steaks were pulled from shelves after just two months of terrible sales.

“The “Trump Steaks” Economy
Just one bite and you can taste the deception”

— SusieQ (@SusieQisBlue) February 9, 2020

7. Trump University

Screenshot / YouTube

Trump University may take the cake, however.

It was designed to be a series of wealth-building seminars which students paid nearly $34,000 to attend. The University claimed to give you access to Trump’s secrets of building wealth.

Turns out, seminars were delivered by motivational speakers often without degrees—some even had criminal records.

Trump’s economic projections make sense only if you studied Economics at Trump University.

— 𝑭𝑶𝑹𝑻𝑰𝑺 (@fortismind) February 11, 2020

8. Trump Vodka

Screenshot / YouTube

In 2006, Trump Vodka popped up for the world to enjoy.

The slogan “Success Distilled” oozed Trump dichotomy. He even expected his T&T or the “Trump and Tonic” to sweep across all bars in the nation.

The vodka failed, of course. The trademark fizzled out and the liquor was discontinued in 2011.

I don’t remember Trump vodka winning anything.

— Miss Shell (@mcriccis) February 10, 2020

9. Trump Network

Source / The Trump Network

Trump network was a bonafide multi-level marketing firm. Otherwise known as… a pyramid scheme.

Previously, the company was known as Ideal Health. Those that worked at the company at the time looked to Trump to change an already troubling business. Many of the sales staff saw Trump as an opportunity to be financially stable after experiencing such hardships at the company.

Turns out, it was just a branding deal and he wasn’t involved as much as people were expecting. He was essentially used for motivational speeches and name recognition, completely misleading employees.

This wasn’t the first time Trump went this route. He was the face of another multi-level marketing company known as ACN.

The Trump Network
Launched: 2009
Service rendered: Vitamin pyramid scheme
Years in business: 2

— NJTrainDelays - your vote is your voice (@NJTrainDelays) September 12, 2019

10. Tour de Trump

Source / Wikimedia

Trump wanted to create America’s own Tour de France.

In classic Trump fashion, he landed big-name bikers, an international team, and a course that spanned the East Coast.

Even for all the high-profile Trumpism, the race only lasted for two years because of Trump’s crippling debt.

Also, LOL at “Tour de Trump.”

— skullsinthestars (@drskyskull) November 15, 2019