– You look great. Trump: Everybody have it? Narrator: Things used to be a lot different for Donald Trump. – Mr. Trump, who’s your
lovely date tonight? This is Melissa. – Hi. Narrator: In the 1980s… Donald Trump was a star. – His name sells. And when you think
business, you think Trump. My son, he’s 22 years old,
and Mr. Trump is his hero. We’re from Oregon, and Donald
Trump is popular out there. He’s my idol. I really respect him,
and I think he’s amazing. Everything he does
seems to turn into gold. Narrator: By 1988, Trump was
a major name in real estate. The New York Times called him one of the richest men in the world, with an estimated net worth of $3 billion. And he bought the luxurious
Plaza Hotel for $390 million. For Donald Trump, the next logical step was buying an airline. – Yo, Joe! – The Trump Organization
was a holding company with various assets. Those assets included
hotels, apartment buildings, and other real estate assets. Narrator: That’s Henry Harteveldt. Donald Trump hired him
as the marketing director for Trump Shuttle. – Mr. Trump thought that having an airline would complement his other
travel-related holdings, and that’s why he was interested in it. – You can fly clear across the USA. Narrator: In the 1980s, air travel was a completely different ball game, especially if you were
flying for business. – The Eastern Air Shuttle, a guaranteed seat without a reservation. Narrator: Shuttle services
from airlines like Pan Am and Eastern offered
flights between New York, Boston, and Washington
that took off every hour. In 1988, a workers’ strike at Eastern drove the airline to a halt. – There was an open
auction for the shuttle. Several different airlines submitted bids. At the end, it became
the Trump Organization and America West, and the
Trump Organization prevailed. Narrator: Trump secured $365
million from a consortium of banks to make a bid
for the Eastern Shuttle. After a meeting with
airline owner Frank Lorenzo at Trump’s Plaza Hotel, the deal was done, and Trump Shuttle was born. – How you doing? Have a good flight. Narrator: Trump Shuttle’s fleet consisted of 21 Boeing 727s. Trump spent $1 million
to refurbish each plane. – We were the first
plane out this morning. We were the most successful
flight this morning. We had more people than anybody else, and I think we had better
service than anybody else. Narrator: Trump Shuttle
offered quick flights between three east coast
destinations: Logan Airport in Boston, LaGuardia in New
York, and Reagan in D.C. – The first week or so was really disorganized because, you know, it was a brand new airline. And the pilots just
got it all figured out. It was 64 flights a day
between three cities, and, you know, it ran like clockwork. Narrator: Trump’s purchase
of the Eastern Shuttle created over 1,000 new jobs,
many of which were filled by Eastern employees out
of work due to the strike. Employees like Rosemary
Durant, a Boston-based flight attendant who got
a job with Trump Shuttle. – I was a flight attendant
with Trump Shuttle from the beginning to the end. I began my career with Eastern Airlines. Towards the end of Eastern Airlines we had the opportunity to bid off to work for the Trump Shuttle. It was strictly a lottery system. It was an opportunity to continue flying, continue getting a paycheck. I had a place to go. I had a job that I loved. I got to continue working. He saved us. – We’re gonna really be a good competitor, and I think it’s gonna be a lot of fun. Harteveldt: So the primary
competitor that we flew against was Pan Am, Pan Am Shuttle,
and a very, very fine competitor to have,
because Pan Am forced us to bring our A game to the shuttle market. Narrator: In true Trump fashion, he soon went after his competition. – I love competing against Pan Am. If you’ve got to compete, I mean, if you’ve got to compete, Pan Am is the one you
want to compete against. Narrator: Trump didn’t just troll Pan Am at press conferences. He also poached their talent, hiring former Pan Am Shuttle president Bruce Nobles, to run Trump Shuttle. – Safety, everyone says, “Oh,
don’t ever mention safety.” I want to mention safety. To me, it’s very important. The safety is number one priority. – There is an unwritten rule
in the airline business: you never attack another
carrier’s maintenance and safety. Mr. Trump attacked Pan Am’s maintenance, and that’s just something you don’t do. Narrator: Trump suggested that Pan Am’s financial struggles might
jeopardize the airline’s safety, and his remarks soon
came back to bite him. – And this represents one of the fleet of your new shuttle
service from here to where? Watch this, Don. Whoa, my God, whoa! Narrator: In August of 1989 … a Trump Shuttle flight made
an emergency landing in Boston when the plane’s front
landing gear malfunctioned. No one on-board was hurt,
but Trump Shuttle’s trouble was just beginning. – Smoke rising from the barracks where the Royal Guard still hold out. Narrator: The invasion of Kuwait in 1990 and the subsequent Gulf War
sent oil prices skyrocketing, and the United States was
on the brink of a recession. – That affected all airlines,
not just the Trump Shuttle. People just were not flying. As far as the Trump
Shuttle became concerned, the bankers said, “Hey, look,” “this is not financially sustainable.” It became clear that the Trump Shuttle would not grow as an airline. Narrator: Trump fired 100 employees. Just 18 months after the
Trump Shuttle launched, the airline had already lost $128 million. In 1992, Donald Trump
decided it was time to bail. Trump Shuttle’s majority
stakeholder, Citigroup, started negotiating a sale with US Air, who still saw value in the product. Donald Trump claimed he didn’t
lose money on the shuttle. He told the Boston Globe, “I’m smart.” “I got out at a good time.” – It seems like he kind of
just washed his hands of it, said the airline business is very tough, and moved on to whatever was next. Narrator: As for Trump Shuttle employees, many of them kept their
jobs and transitioned to becoming employees of the
newly-named US Air Shuttle. – [David Manley] It
really wasn’t a failure. I think it was pretty successful. I mean, Trump saved our
careers, I mean, absolutely. They really took care of their employees. My wife, who had breast cancer, the CEO of the company,
he said, “Hey, any bills” “that aren’t covered,
just leave it on my desk.” I left some bills on those desks. It was like, I don’t know,
a $30,000 pharmacy bill. You know, that’s how I was treated, and so I’m sure that came down from Trump. I don’t have anything bad to say.