How Donald Trump Got Taken to the Cleaners Buying Trump Shuttle and The Plaza Hotel

Donald Trump’s sine qua non is dealmaking. He declares he doesn’t just make deals, he’s the authority on making deals because he literally wrote “the Art of the Deal.”

I recently picked up a copy of Trump: THE GAME by Milton Bradley. Because it’s not whether you win or lose but whether you win!

Politico shares the deal making that went into Trump’s purchases of an airline and The Plaza — both of which came within 12 months of “literally writing The Art of the Deal.”

[H]e purchased the Plaza Hotel because he openly coveted the Manhattan landmark, so much so that he paid more for it than anybody anywhere ever had spent on a hotel—$407.5 million—a hotel that wasn’t turning enough profit to service the debt to which Trump committed.

And in the fall, he agreed to buy the Eastern Airlines Shuttle, which he wanted to rename the Trump Shuttle, for a sum that analysts and even his own partners considered excessive—more than the airline itself thought the shuttle was worth.

“I went to him,” Frank Lorenzo, the former Texas Air chairman, who sold Trump the shuttle, diplomatically told me in an interview. “I think our number was 375, 385”—million—“and he negotiated it down”—to $365 million. “Your offering price is always higher than you think you’re going to get,” Lorenzo said. From Trump, he almost got it, anyway.

“The price was too high,” said Bruce Nobles, the former president of Trump Shuttle, who was involved in the negotiations—and Lorenzo, not Trump, set the tone. “He said, ‘This is what I want.’

“It was not a lengthy financial analysis,” added Nobles, describing it as “back-of-the-envelope” and “very quick.” “Lorenzo said, ‘I really want to sell it,’ and Donald said, ‘I really want to buy it.’”

Trump only put $20 million of his own money into the airline, and the airline didn’t make nearly enough to service its debt. With no buyers, Trump lost the airline and the banks that had financed the Trump Shuttle deal contracted with US Air to run the operation in 1992. US Air only part-owned the operation (they purchased the remainder in 1997), taking a 40% stake and a 10 year management contract.

Ultimately Trump lost much more than his original investment, forfeiting over $100 million he had personally guaranteed.

Trump also sought to take over American Airlines just a year into his foray as an airline operator. Trump likely never had financing for his offer, and may have been looking to simply make a trading profit on the American shares he did buy as a greenmailer (an amount below the SEC reporting threshold). He ultimately lost money on the offer, though, caught up in the 1989 Friday the 13th stock market mini-crash.

I at least expect to be able to resell my Trump board game for more than the $20 I paid for it.

About Gary Leff

Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

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  1. Well cool at least he is as stupid as what we have in the white house now….so the transition when he becomes president should be of little or no disruption to the Washington elite….LMAO Please let us know when you sell the board game what percentage of the proceeds you gave to Bernie’s campaign……because you should be spreading the wealth!!

  2. Gary, Please stop with these purely political posts. I can get more than my fill of Presidential politics non-stop on virtually every media outlet.

    I hate that you have me defending DT, but here goes: At least the guy has a record of both success and failure in THE PRIVATE SECTOR. Haven’t we had enough of life-long government apparatchiks who have never had to meet a payroll or ever hired one person. How’s that been working out?

  3. So he inherited money from daddy and has had many business failures and bankruptcies. At least we will all sleep better at night once the grudge-holding bully narcissist is in charge of the FBI, CIA, American military and nuclear arsenal, right?

  4. Lost one hundred million
    That’s Trump change for the Donald
    Wait till he can write those checks from the Oval office
    Thats if he hasn’t destroyed the world by then with world war 3
    He is perhaps the scariest candidate in my lifetime

  5. Sounds like Gary wants a job with CNN. Anyone can spin only the bad stuff. Can do that about any candidate or person. Best to stay away from politics. I agree with Kenny. Another useless post. Too bad because you used to have a lot of good ones.

  6. I’m a fan of DT. That said, I disagree with the above posters stating this article is a hit piece. Gary devotes a fair portion of his coverage to airline industry topics, as opposed to being solely focused on miles/points. As such I would say this article is informative and relevant to his subject matter. It’s certainly rare to have a presidential candidate with any past involvement in the airline industry. That DT has had several business failures is a matter of fact, and not necessarily a purely shameful one. Had Gary “poured on” to the facts to add insult to injury, then I would feel differently. I only write this because I have seen multiple posts on different articles accusing Gary of blatantly slanting left or against DT. I just wanted to state my disagreement.

  7. What have been Donald Trump’s views — note the use of the plural — when it comes to airline deregulation/regulation?

  8. @GUWonder As far as airline industry policy views, he argued that he should be allowed to fly with a 2 pilot cockpit rather than the 3 that Trump Shuttle aircraft required at the time.

  9. The Donald is returning the favor. He is taking Americans to the cleaners and they are so happy about it.

    It’s good to be Donald because you can cuss at women and they want to sleep with you. What do his wife and daughters think? Thank you for putting us in our place daddy!

  10. Gary,

    I’m not a Trump supporter.

    But I don’t get the whole “he had a business failure” angle. Maybe from pundits or pure haters, but from real business people? Every successful business person you ever meet can rattle off the failures and missteps they had, and tell you how they contributed to their most recent successful venture(s). The myth of overnight success gets dispelled very quickly. I’m am 100% positive this applies to View from the Wing too, am I right? Someone involved in a bunch of businesses, OF COURSE they are going to make some bad ones from time to time, just like a travel hacker will make many bad decisions on the road to becoming a guru (and even then, they will probably “leave something on the table” periodically.)

    Like I said, I don’t think Trump is a good fit for government, but I’m on the side of people trying to make it in the business world here. It seems hypocritical that someone that should know better would cherry pick bad business outcomes when the portfolio of work as a whole is what defines business success.

  11. Most trump fans won’t read this. A lot of them can barely read, I would imagine. Don’t forget – he LOOOOVES the poorly educated…..

  12. @roloT, how does experience in the private sector, particularly in private companies, translate in any way to being an effective president? Or any public official? As head of his companies, his job has been to make as much money as possible for himself. He has never shown any awareness that he has to meet a payroll. If he doesn’t meet a payroll, he doesn’t give rats ass if his employees are starving. If he ran a public company that he did not control, at least I could equate his shareholders to the public tax payer, but he has not.
    The government (any government) is not intended to turn a profit. They are supposed to operate in the public interest, so private sector experience has zero relevance to how good or bad a president someone will make. The mark of a good politician is how they have used power to improve the lives of the public. On this count, DT fails miserably. He has never done anything that was not in his own best interest. If he contributes to a charity, it is to aggrandize himself. The only person Donald Trump will ever care about is Donald Trump.

  13. No, the gov’t isn’t supposed to turn a profit, but it’s not supposed to be trillions in debt either. Politicians have no idea how to run an entity successfully. And I HATE that I’m even writing this – this is NOT a political blog. Can you please keep to what we’re all here for. I don’t care who you are backing/hating for Pres

  14. Have you ever been associated with a failed business venture? Maybe even in the mile and point arena?

  15. farnorthtrader, I have no idea if DT or any business person would be an improvement. My point was that, on the federal level, we are loaded with career politicians who, in many cases, have never even held a private sector job ( except when the go thru the revolving door of public sector to private sector to enrich themselves). They have no idea how to run a yogurt shop let alone a multi-trillion $$ economy.

    And please, criticizing DT because he selfish. Are you kidding me or are you naive? Do you think altruism is the reason a person fights tooth-n-nail to stay in the Congress/Senate? I got news for you, it’s not. HIt’s power & wealth. People like Kasich (for example) who was politicking in his early 20s, continue to pursue politics because they can be the governor of a state and spend more than one year not doing the job they are being paid to do…..while looking to get a better job. Yeah, that happens all the time in the private sector.

  16. Donald has a habit of rewriting history. Today he boasts of how Trump Shuttle was such a successful deal. That’s not what he was saying 23 years ago shortly after he got rid of it. I was in the audience when he gave a speech about his various business ventures, and he clearly said that the Shuttle had been a huge mistake and that “airlines are a terrible business”. He repeatedly moaned about how “everything costs $100,000…If a cockpit window breaks, it’s $100,000. If a baggage systems breaks, it’s $100,000….” Funny how he remembers it differently now.

  17. Trump also literally wrote that he sleeps with other people’s married women, secretly, on Page 271, Paragraph 1, in his book “Think Big & Kick Ass” (hardcover edition), ISBN: 978-0-06-154783-6. Now, although this book was his best, he still wrote adultery is okay, no problem, boasted about it, admitted to it, probably still does it, and the US Media will just ignore it.

    Ahh, no. I voted for Ted Cruz.

  18. Great, another travel blog turns into a Lib-tard’s ‘insights’ on politics.

    This was a moderately interesting blog that will be removed from my bookmarks.

    As the flight attendants like to say: Buh-bye

  19. The difference is that Trump (if elected) would be playing with tax payers money. How many bankruptcy failures can we afford? He can still walk away from his debts and thinks nothing of it, but can the USA? That’s what makes him so scary.
    BTW: Travel is greatly affected by government regulation and by the economy, so why not discuss these things?
    And, I don’t care for any of the “final four” but we’re likely to be stuck with one of them.

  20. @ Rudy – Don’t let the door hit your 500lb rear end was you waddle out to the klan meeting/Trump rally.

    The GOP’s Frankenstein monster is turning on it’s creators, who thought they had a great scam going realizing that a third of the population are dumb enough to vote against their own interests if they could be recruited based on their prejudices alone. While they still are too stupid to know their own economic interests, they have a new Pied Piper who cuts straight to the hate and is the billionaire most of them tell pollsters they expect to be – ostensibly the reason they allowed shifting most of the middle class wealth to the top 1%.

  21. How is pointing out Trumps failures “bashing on him”. The guy is a “LOOOOOSSSSSEEERRR” who happened to be born with a silver spoon in his mouth. He has used the “system” to get where he is, whether it is stiffing banks, or shutting down businesses. Grow up.

  22. I can’t stand these crying democrats, putting down trump. I’m not the biggest trump fan but he’s way better then crooked Hillary. Benghazi, Deleted emails, Hillary “fund” how about the name Juanita broaddrick. Look it up. Cover up after cover up. She’s a scumbag. My personal favorite, when Bill Clinton presidency term was up. The Clintons took the furniture in the White house. Overall, Clinton’s don’t give a crap about the American people. Trump is a million times better then this low life!! Wake up people. Be thankful she isn’t in office. Shows how dumb the american people can be. Who the hell would vote for her ??

  23. Not the biggest Trump fan? Of course not; you’re not Donald Trump. It’s to the point where literally every sentence Trump utters is a lie. Yeah, I know; “Hillary’s evil”. Fox News and Rush Limbaugh get all the credit for that illusion. Too much work for a lazy ass like Trump. He’d rather call women who don’t give him what he wants “nasty”. Trump has his own rapey past seems to eclipse Bill Clinton’s (who was not running in 2016) in scope and severity.

    Now Trump needs to get re-elected to stay out of prison for a myriad of financial crimes (about 3 dozen investigations into different crimes will proceed upon his defeat). He’s not gonna make that corner.

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