Donald Trump is a winner. He is so much of a winner, that even when he is losing, he is still winning; THAT is how much of a winner Donald Trump is. All he does is win win win win.
Except for when he bought that airline back in '88.
Reagan was still in office. George Herbert Walker Bush had swept Bob Dole in the Republican primaries and was about to crush Michael Dukakis in the general election. We hadn't yet gone to war in the Persian Gulf. Oil prices were already starting to spike, leading to a recession that would start in a little over a year. And in October of that Year of Our Trump, Anno Donaldi 1988, Donald Trump proudly peacocked at the Plaza Hotel in Midtown Manhattan (which he had also purchased that year and which would later be offloaded in a 1992 bankruptcy filing) that he had acquired Eastern Air Shuttle, a 27-year-old air shuttle company that exclusively served the Eastern Seaboard, with flights between New York, Boston, and DC.
Remaking Eastern Shuttle in his own image
Eastern Shuttle's operation model was brilliant for business travelers, but almost unimaginable in today's post-9/11 world. Though the fleet of planes was nothing special, the promise was that if you showed up for a flight, you were guaranteed a seat. There were no advance tickets and no check-ins. Like a bus or train ticket, all you had to do was show up. There were hourly flights with more seats than passengers, so there was rarely a capacity issue. In the rare instances in which flights were full, they would just bust out another plane to accommodate the overflow. Which sounds like a great concept for customers, but if that is how airlines generally operated in the halcyon TSA-free days before 9/11, it's no wonder they had to be bailed out in 2002.