Donald Trump's tax returns have revealed that his businesses are far less successful than he'd have you believe. The US president paid no federal income tax in 10 of the last 15 years, according to The New York Times. This was largely because he declared substantial losses on his businesses which he said outweighed his income. Furthermore, his three golf courses reported $US63.6 million in losses between 2010 and 2018.
All of which will come as little surprise to anyone who has taken even the most cursory glance at Trump's entrepreneurial back catalogue – he is certainly no stranger to a failed enterprise. Over1 the years he's launched a string of dubious businesses, including (but not limited to) GoTrump.com (a travel search engine), Trump Ice (spring water), Trump Steaks and Trump Vodka. There's even Trump: The Game, his answer to Monopoly.
He also tried his hand at aviation. Back in the 1980s both Pan Am and Eastern Air Lines ran profitable no-frills "air shuttle" services up and down the US East Coast. However, when Eastern Air Lines ran into financial difficulty at the tail-end of the decade, and sought to offload some of the routes, Trump sensed an opportunity.
He snapped up a fleet of 21 ageing Boeing 727s from the struggling carrier at a remarkably modest price, along with many of its disgruntled staff, and took over the two routes linking New York with Boston and Washington D.C.
Trump Shuttle was launched in 1988 accompanied with a pledge to create "the best transportation system of any kind in the entire world."
While Eastern's "shuttle" services were unashamedly no-frills – regular passengers dubbed it the "cattle car" – Trump wanted to offer luxury. He spoke of turning the airline into "a diamond". So, naturally, those aircraft needed a Trump-style makeover. Anyone who has stayed in one of the president's bling hotels will know what that means.
"We took old 727s and spent a huge amount of money stripping them down to the frame and refurbishing them with chrome seat belts, maple bulkheads and faux marble bathrooms [real marble would have weighed the aircraft down]," Bruce Nobles, a former Pan Am executive and president of Trump Shuttle from October 1988 until June 1990, told The Globe and Mail in a 2011 interview. "It was a problem: we spent too much money on the airplanes."
Nobles claims Trump paid $US365 million for the aircraft and landing slots, borrowing $US380 million from a consortium of banks and putting in around $US20 million of his own cash. The sale took months to receive approval, however, so the first flights didn't take off until June 8 1989. The inaugural services featured all the ritz one would expect – all string quartets and flowing champagne – although bad weather forced the first departure to Boston to leave 45 minutes late, making a mockery of Trump's full-page newspaper ads promising punctuality ("7am does not mean 701am", they read).
Describing the on-board experience for CN Traveller, Barbara Peterson wrote: "I flew a couple of times on the Trump Shuttle in its final days, and the flights themselves were perfectly pleasant. In the lounge-like gate areas, you could pick up a free newspaper or snack; in-flight, there were bagel breakfasts in the morning, and complimentary cocktails with boxed meals later in the day.
"But what I also recall on a trip from D.C. to New York was that I was barely into my chicken Caesar salad and chardonnay when the 'prepare for landing' call came from the cockpit. The not-so-glamorous reality is that it was a 45-minute flight, and about 20 of those minutes were spent getting up and down from cruising altitude. The service was classy, yes, but it was sort of like having the 21 Club cater a Greyhound bus trip."
Even the flight attendants were given swish new uniforms, featuring fake pearl necklaces. Other innovations were sidelined, however, including full-length mirrors in the bathrooms (too heavy), plush burgundy carpets (drinks trolleys couldn't be pushed across them) and an in-flight magazine all about Donald Trump.
The hype seemed to work. Trump Shuttle grabbed a decent market share (Pan Am said 40 per cent; Trump claimed 50), and even a landing gear failure on a flight to Boston, which saw one of his jets land in a shower of sparks, could not deter travellers. However, it struggled to thrive economically in what was a tricky economic climate; and those high-frequency 45-minute flights, using ageing aircraft, were costly in terms of fuel, maintenance and landing fees. It was all style and no substance, basically.
Trump blamed Nobles, whom he jettisoned in June 1990, and set about forming a new strategy. "Trump Shuttle is an aesthetic success," he told the media at the time. "It will be a financial success, but right now I'm upset with the people running it."
In an attempt to turn around its fortunes, the new management team planned to offer leisure services to Mexico, the Caribbean and Atlantic City, giving passengers a little more time to enjoy their Caesar salads, but it was too little too late. Trump missed an $US1.1 million interest payment in September 1990, the loans were defaulted, and ownership of the airline passed to the banks, who eventually sold it to the US Air Group.
"It worked out well for me," was Trump's assessment in an interview with The Street. "I ran an airline for a couple of years and made a couple of bucks [others estimate the airline lost $US128m]. The airline business is a tough business, [but] I did great with it."
Five other ill-conceived airlines that flopped
German financier Alexander Schoppmann said he was coming to the rescue of nicotine lovers all over the world, when, in June 2006, he announced the launch of Smintair – an airline which allow passengers to smoke throughout the journey. A triple portmanteau of Smoker's International Airways, the carrier promised to "bring back the exclusivity in flying encountered in the 1960s".
"The upper deck will be the passengers' lounge and not be jammed with seats, as you can sadly find everywhere, nowadays," the website added.
"Allergics against tobacco smoke or militant anti-smokers are asked to not apply," said Smintair on its jobs page.
Flights from Dusseldorf to Nagoya, Japan were mooted, but, alas, the £27.6m needed to turn it from idea into reality was never raised.
Seriously, this existed for three glorious years. It was conceived as an unconventional way of raising awareness of the restaurant chain, but expanded to encompass a fleet of seven aircraft covering 17 destinations, including The Bahamas, Fort Lauderdale, Orlando and Las Vegas. Two "Hooters Girls", wearing the standard skimpy attire, assisted the (conventionally dressed) cabin crew, and the carrier did its best to woo affluent travellers with plenty of legroom and free meals on all flights over an hour. It ceased operations in 2006, and is estimated to have cost the firm $US40 million.
Hardly an "airline", as it operated for just one flight in 2003, this brainchild of Castaways Travel, a Houston-based "clothing optional" (and still in business) firm, shuttled fliers from Miami to Cancun wearing nothing but their birthday suits. The idea was picked up in 2008 by a (surprise, surprise) German travel agency, which flew nude sunseekers from the city of Erfurt to the (rather chilly) Baltic seaside.
Overestimating the demand among dogs for a week in the sun, Pet Airways unveiled itself in 2009, offering fares based on the size of the animal and the distance travellers. Pets ("pawsengers" is how the carrier described them), were checked in at the airport by their owners, who could then track their progress online. Operations were handled by Nebraska-based Suburban Air Freight, but financial problems surfaced in 2012 and the following year it was consigned to airline heaven.
Aussie pilot Craig Justo launched this oddity in 2006, offering randy couples the chance to join the Mile High Club in his twin-engine Beech H-18S. $US725 bought each couple bubbly, bedding and an hour in the sky – plus a certificate to take home. Needless to say it didn't take off.
And 10 more with very strange names
Touch and Go
Russian charter airline that was hugely unpopular with nervous fliers. Ceased operations in 1997.
Hungarian budget airline – also slang for "urinate". On the website, there's a section called "My Wizz". It is still going strong.
Brasil Rodo Aereo. Low fare carrier based in Sao Paulo. Cash-strapped, it ceased trading a few years back.
Prone to hijackings, this Pennsylvanian carrier flew from 1967 to 1995.
Spanish airline. Sounds like a combination of spandex and tampax. Folded in 1988.
Ghanaian carrier, lasted just two years (1997-1999).
Low-cost carrier launched in 2013. "We chose vanilla as our brand name because it is popular and loved by everyone in the world," the airline president Tomonori Ishii said at the time. "I think it is a very cute name." Mr Ishii was apparently unaware of the bland and plain associations with the word "vanilla" in the West.
On a runway, we presume. Taiwan-based; folded in 2000.
Planes do not run, they fly.
The Telegraph, London