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Trump cartoon © Lisette Brodey/Pixabay
Trump cartoon © Lisette Brodey/Pixabay
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The Time Trump Bought An Airline And Crashed It

Picture of Nikki Vargas
Travel Editor
Updated: 9 February 2017
The U.S. election has become a circus, a veritable performance where, in the words of Shakespeare, “all the world’s a stage, and all the men and women merely players.” On the left, we have Hillary Clinton, the quintessential politician on the verge of making history as the first female president in American history. To the right, we have Donald Trump, the reality-star-turned-politician whose impulsive behavior both launched his stardom and now threatens his campaign. Trump, who prides himself on an enormous business acumen, has a myriad of failed business endeavors in his past. Far beyond Trump Steaks and Trump Vodka, Trump Airlines probably best captures the risky business of our Republican presidential nominee.

On a crisp day in October 1988, Trump (then 42) strode into the Plaza Hotel with the now familiar confidence he reserves for his campaign rallies. The Donald was excited, having just purchased Eastern Air Shuttle, a 27-year-old airline company operating flights between New York, Boston, and Washington D.C. Lacking any knowledge of the airline industry, it seems Trump sought another business to slap his name on.

“At the time, he was expanding his casino business [in Atlantic City], jet fuel was still relatively cheap. [The purchase] was a combination of vanity and the lure of an appealing business,” Trump sources told The Daily Beast.

Trump tower © quintheislander/Pixabay
Trump tower | © quintheislander/Pixabay

This wasn’t Trump’s first business venture outside of real estate and wouldn’t be his last. Earlier this year, Rolling Stone released a searing article that exposed 13 failed companies Trump previously invested in. There was Trump Steaks, which Trump inexplicably sold at futuristic tech store Sharper Image. There was Trump Magazine, which launched in 2007 and aimed to capitalize on luxury advertising only to fold in 2009 due to the financial crisis. There was the travel search engine, which he hoped would compete with Expedia and Orbitz. But the site proved to be more a vanity platform than anything else, as travel planners were greeted with a collage of Trump’s photos; the site closed a year after its launch.

Trump’s past is a graveyard of misplaced ambition, but it is his airline that best encapsulates the qualities of the presidential candidate we see today.

The idea behind Trump Airlines was simple: the shuttle would promise the ease and convenience of “catching a bus,” a pre-9/11 idea that would be impossible in this post 9/11 world. Trump Airlines guaranteed that travelers could simply show up — no check-in or advance tickets required — and be guaranteed a seat on a flight. The idea wasn’t bad. In fact, it’s a similar concept to present-day Delta Shuttle. But it was Trump’s vanity that, like so many other endeavors of his, kept the flights grounded.

Donald Trump | © DonkeyHotey/Flickr
Donald Trump | © DonkeyHotey/Flickr

Paying $365 million for a fleet of 17 Boeing 727s, Trump bragged about his expert negotiations in securing a “good deal” (sound familiar?) down from $400 million. The jets were old (very old, in fact) and so Trump invested an additional $1 million per jet to fund the redesign. The planes were “Trump-ified” with a giant “T” painted on the tail and the TRUMP logo branded on the side. The interior of the plane was designed to resemble one of Trump’s hotels – complete with maple wood paneling, gold-plated bathroom fixtures and faux marble sinks.

“At first they wanted to put in a ceramic sink, that was too heavy,” Nick Santangelo, who ran maintenance and engineering on the shuttles, told The Daily Beast. “Then one of [Trump’s] henchman decided they were going to put brass handles on the doors you use to get out in an emergency. Normal handles weigh a few ounces, and these things probably weighed five pounds each. You’d kill to save one pound, and they wanted to add 20-30 pounds to each plane.”

While most airline CEOs understand the aerodynamics of a plane, Trump chose luxury over logic in many cases. The planes were too heavy, the fuel cost too high, and the amenities unnecessary for a 45-minute flight. Trump Airlines launched in the summer of 1989 with all the pomp and circumstance expected of The Donald. Tuxedo-clad servers carted chocolate truffles at Logan Airport, while Trump took the stage to celebrate the inaugural Trump flight. Rather than stick to a celebratory speech, Trump bashed competitor, PanAm Airlines, which horrified investors and employees.

“I wouldn’t fly them,” said Trump, “they’re losing money and their planes are old.”

“We said, ‘Donald, don’t ever do that again,'” recalled former Trump Airlines marketing director, Henry Harteveldt to Boston Globe. “It was wrong. We had no proof to back that up; and there’s an unwritten rule in the airline business that you don’t attack someone else’s safety record.”

Trump Shuttle | © Aero Icarus/Flickr
Trump Shuttle | © Aero Icarus/Flickr

Of course, the claims were unsubstantiated and meant to pivot from Trump’s own airline facing an onslaught of problems. In fact, a mere three months later Trump airlines snagged headlines when a flight made an emergency landing in Logan Airport due to malfunctioning landing gear. Yet, shifting attention away from the truth is a song-and-dance Trump has perfected. If eluding the truth is an art, then Trump is indeed an artist.

In September 1990, the Donald defaulted on his loan payments and gave up control of Trump Airlines to the banks. In other words, Trump Airlines never (ahem) got off the ground. Citibank eventually sold Trump Airlines to US Airways in 1992. The planes were stripped of their “Ts” and today are still being flown, soon to join American Airlines as part of the US Airways merger.

The story of Trump Airlines is conveniently omitted from Trump’s own biography and is a failure he refuses to accept. When asked about the airline, Trump has blamed the industry, the economy and circumstance but never his own failings. The similarities between “Trump: the aspiring airline mogul” and “Trump: the aspiring president” cannot be missed. Father Time has hardly curbed the bravado and uninformed insults that have become synonymous with The Donald.

Trump Rally| © Gage Skidmore/Flickr
Trump Rally | © Gage Skidmore/Flickr

In the end, the story of Trump Airlines is a lesson for the masses rather than Trump alone. “He really didn’t understand the business,” said former Trump Shuttle president Bruce Nobles to The Daily Beast. “That was his style and it really hasn’t changed.”

As Trump now chases his latest impulsive endeavor, the White House, we are left with an age old lesson: fool me once, shame on Trump; fool me twice, shame on us.