Trump to me has been especially inept at operating anything that flies for a profit because he just doesn't have any sense of what people want to ride in airplanes for.
The Shuttle was a city bus with wings. It's utility was it was a cheap, easy and convenient way to go from Boston to NYC to DC and back, without having to plan ahead, pay out the nose or give it much thought. It was slightly more hassle than jumping in a cab. That said, you didn't fly on the shuttle for luxury, you didn't want to pay 80% more to sit in the front and get free drinks on a 45 minute flight and get better service. "Something came up, I need you in New York this afternoon, jump on the shuttle and someone will meet you at LGA" If you wanted great service, you got a regular flight and booked first class. If you wanted to be a big shot, and have gold toilet seats and rich leather upholstery, you booked a private jet. Trump thought he could run the shuttle like a private jet service, and that it was better to run a service where he could charge $900 for a seat if he had better decor than the $45 a seat the shuttle was charging when he bought it (he thought the way to make it profitable was to make it a luxury service, oops).
Seriously, its like he bought the NYC Subway and decided to put fancy cars in, put marble lobbies in the subway stations, charge $600 to go from Queens to Coney Island and we'll all be rich! (well, almost, you'd also have to adjust that to account for there being another subway running the same routes and sticking with the same shitty lobbies and cheap fares)
I'm pretty sure his Helicopter service was something kind of like that. The people who want luxury helicopter service are either rich enough to have their own luxury helicopter or they expect it for free as part of the room rate when they travel. CEOs of public companies can't pay that kind of money, not because they can't afford the cash, but because they can't afford the publicity. Even if they use their own money, it looks bad.,Shareholders might not mind owning a jet, but they'll go nuts when you pay to rent one, to play golf anyhow.
Its all a symptom of him never having to run a real company that needed to make real profit. He thought everyone could just hop on the private jet, why not? Its what he did. Minions, especially the minions who fly the shuttle, are the $45 ticket guys. And again, the people who want gold toilet seats between New York and DC and Boston have their own plane with their own gold toilet seats.
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