The 20 Craziest Career Milestones On Donald Trump’s Path To The White House

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Donald Trump’s victory in the race for the White House shocked many Americans and stunned even more on-lookers from around the world. After all, this is a man once appeared in a soft-core movie and even has his own board game. In fact, here are 20 totally insane career moves that you would never have expected from a president.

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20. He appeared in a Playboy movie

Trump’s career path is anything but normal. For instance, in 2000 the president-elect popped up in one of ’s soft-core adult movies. In fact, he can be seen in Playboy Video Centerfold: Playmate 2000 Bernaola Twins welcoming playmates with a bottle of champagne.

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19. He’s in the WWE Hall of Fame

Believe it or not, Donald Trump is in the World Wresting Entertainment Hall of Fame. He was inducted to the list of professional wrestling personalities in 2013 after hosting WrestleMania IV and V. He also took part in something called “Battle of the Billionaires.”

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18. He owned a bunch of beauty pageants

Your future president used to own the Miss Universe Organization, the group responsible for such pageants as Miss USA and Miss Teen USA. In 2015, though, he sold the rights to the group, likely prompted by NBCUniversal’s decision not to air Miss USA 2015. The network issued a statement that read, “Due to the recent derogatory statements by Donald Trump regarding immigrants, NBCUniversal is ending its business relationship with Mr. Trump.”

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17. He ran Trump University


Trump seems like the perfect person to learn business skills from, right? Well, his Trump University ran a real estate training program between 2005 and 2010. But the for-profit limited liability company never received accreditation. In fact, TU has subsequently been beset by lawsuits.

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16. He built a skyscraper and named it after himself

Well, what else would he call it? The president-to-be lives with his wife Melania on the 66th floor of Trump Tower in New York City. The penthouse is valued at $100 million and has views of both Central Park and downtown Manhattan. It is also plastered in gold, with marble floors and columns.

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15. He ran a casino called the Trump Taj Mahal


Here’s something that you don’t see that on every LinkedIn profile: Donald Trump opened a casino in Atlantic City and named it the Trump Taj Mahal. However, despite the billionaire dubbing it the “eighth wonder of the world,” the casino went out of business in October 2016. In fact, Trump has taken his Atlantic City casinos to bankruptcy court four times.

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14. He hosted a reality TV show for years

In a career move that couldn’t be considered presidential by any stretch of the imagination, the Donald hosted The Apprentice between 2004 and 2015. And, of course, he notoriously stated that all of the female contestants flirted with him either “consciously or unconsciously” during the production.

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13. He wrote a book about golf


Yes, you read that correctly. In addition to his popular business memoir The Art of The Deal, the real estate tycoon penned a whole book about golf. It’s called The Best Golf Advice I Ever Received, and it’s a collection of, you guessed it, golf advice.

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12. He dropped out of college

The president-elect left Fordham University in New York because, in his own words, he thought it wasn’t hard enough. In fact, after two years, he moved to the University of Pennsylvania. He later said, “I decided that as long as I had to be in college, I might as well test myself against the best.” Apparently, though, some current Fordham students don’t wish to acknowledge that Trump attended their school.

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11. He has a star on the Hollywood Walk of Fame


In 2007 the future leader of the free world was strangely given a star on the Hollywood Walk of Fame. He won’t be the first president to have a star on the fabled walkway, though: former actor Ronald Reagan has one too.

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10. He earned a Razzie award for worst supporting actor

Still, it turns out that there is some acting work on Trump’s IMDB page too. In fact, he starred with Bo Derek in a crime fantasy movie from 1989 called Ghosts Can’t Do It. He even won an award for his performance. However, that award was a Razzie for worst supporting actor.

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9. He was dubbed the class “Ladies’ Man”


It’s fair to say, then, that the future president has a history of pursuing women. After all, Trump’s photo was labeled “Ladies’ Man” in his 1964 yearbook from the New York Military Academy.

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8. He pulled out of the 2012 presidential race to host a TV show

In 2012 Donald Trump made one of the most startlingly decisions in his career. Yes, he decided not to run for president because he wanted to continue hosting a reality TV show. Interestingly, he had already decided not to run for president on three previous occasions.

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7. He took control of his father’s business three years out of college


Yes, Donald Trump got a job straight out of college and rose to the top of the business in just three years. However, that business was his dad’s real estate company, so maybe he had already had a foot in the door.

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6. He might not have paid taxes for almost two decades

In 1995 Trump declared a staggering loss of $916 million for his income tax returns. Reportedly, those losses could have allowed him to avoid paying income tax for 18 more years. This is very surprising, given how Trump is so sure of his business know-how that he felt compelled to write several business advice books.

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5. He released his own board game


In 1989 the Donald released a board game, but there are no points for guessing the name and theme. Of course, Trump: The Game was a Monopoly-style ordeal where players had to buy real estate and try to out-trump each other. Trump and makers Milton Bradley hoped it would sell two million units. However, it apparently came nowhere near that.

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4. He had his own airline

Of course, Trump isn’t one to be put off by his past professional failures. So in 1989 the businessman bought an airline route, and the first Trump Shuttle took flight. Reportedly, Trump spent ridiculous amounts to smother the planes in gold and mahogany, and the company never made a profit.

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3. He produced a Broadway comedy


Apparently, in 1970 Trump invested $70,000 in a Broadway play just to get a credit as a co-producer. The comedy was called Paris is Out!, and it closed after just 96 shows.

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2. He opened a steakhouse

However, like a lot of other items on this list, his restaurant was a flop. Yes, Trump Steakhouse in Las Vegas was shut down in 2012 for a whopping 51 health code violations. According to some reports, the eatery even served five-month-old duck, and we’re not talking confit de canard.

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1. He produced Trump Vodka


Fancy a Trump and tonic? No? You’re not alone. Indeed, Trump’s eponymous range of vodka was shelved just four years after its glitzy launch in 2007. The bottle was shaped like a giant gold skyscraper, because what else would it be?