Trump’s billion-dollar loss — I was his ghostwriter and I saw it happen

Currency

On Tuesday, the New York Times scooped the world on the news that from 1985 to 1994, Donald Trump incurred the biggest business losses of any single taxpayer in American history. What was it like for him to lose more than $1 billion in a decade? Was he perpetually ashen-faced with fear? Or smirking at the thought of outwitting the IRS “for sport,” as he said in a Wednesday morning tweet?

I happen to know, because from late 1988 to 1990, I was his ghostwriter, working on a book that would be called Surviving at the Top. Right in the middle of this period, I can tell you that the answer is that he was neither. Except for an occasional passing look of queasiness, or anger, when someone came into his Trump Tower office and whispered the daily win/loss numbers at his Atlantic City casinos, he seemed to be bored out of his mind.

I tend to see my time with him — the first part of it, anyway, before things started going bad in a hurry — as his “King Midas” period. I never said this to him; if I had, he probably would have thought I was suggesting he enter the muffler business. But it was a stretch of months when everything he touched turned into a deal. The banks seemed to accept the version of him depicted in his first book, The Art of the Deal, which we now know from his previous ghostwriter, Tony Schwartz, was entirely invented. They believed it over what they saw on his balance sheets or heard coming out of his mouth, and never said no to his requests for more money. Often they came up with things he could say yes to before he could think of them himself. As a result, a failing real estate developer who had little idea of what he was doing and less interest in doing it once he’d held the all-important press conference wound up owning three New Jersey hotel-casinos, the Plaza Hotel, the Eastern Airlines Shuttle and a 281-foot yacht.

Donald Trump with Alfred Eisenpreis, New York City Economic Development Administrator. Sketch of new 1,400 room Renovation project of Commodore Hotel.

(Photo by NY Daily News Archive via Getty Images)

Donald Trump pauses in his apartment 5/20 after receiving the news that the Board of Estimate unanimously approved a 40-year tax abatement plan. Under the plan Trump will purchase and refurbish the Commodore Hotel, which closed into doors 5/18, from the Penn Central Transportation Corp. In return for his $10-million-dollar purchase and up to $100 million face-lifting investment, Trump will have no real estate taxes for 40 years.

(Bettmann via Getty Images)

Real estate developer Donald Trump announces intentions to build a $100 million dollar Regency Hotel.

(Photo by John Pedin/NY Daily News via Getty Images)

Donald Trump stands behind architect’s model of City Hall Plaza.

(Photo by Frank Russo/NY Daily News Archive via Getty Images)

Donald Trump and Ivana Trump attend Roy Cohn’s birthday party in February 1980 in New York City.

(Photo by Sonia Moskowitz/Getty Images)

Donna Mills and Donald Trump during 1983 Annual American Image Awards at Sheraton Center in New York City, New York, United States.

(Photo by Ron Galella, Ltd./WireImage)

Donald Trump attends 38th Annual Horatio Alger Awards Dinner on May 10, 1985 at the Waldorf Hotel in New York City.

(Photo by Ron Galella/WireImage)

Portrait of real estate mogul Donald John Trump (b.1946), smiling slightly and facing to his right, 1983. New York.

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Boxing promoter Don King holds up the arms of Mike Tyson and former champion Larry Holmes during a press conference here 12/1. Looking on is Donald Trump. The fight will be held at the Trump Plaza Hotel.

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Donald Trump, real estate mogul, entrepreneur, and billionare poses in the foyer of his home in August 1987 in Greenwich, Connecticut.

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Donald Trump Jr. and Donald Trump during 1988 U.S. Open – September 3, 1988 at Flushing Meadows Corona Park in Queens, New York, United States.

(Photo by Ron Galella, Ltd./WireImage)

Ivana Trump and Donald Trump during Mike Tyson vs Michael Spinks Fight at Trump Plaza – June 27, 1988 at Trump Plaza in Atlantic City, New Jersey, United States.

(Photo by Ron Galella/WireImage)

Billionaire Donald Trump and his wife Ivana arrive 04 December 1989 at a social engagement in New York.

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Donald Trump and Daughter Ivanka Trump during Maybelline Presents 1991 Look of the Year at Plaza Hotel in New York City, New York, United States.

(Photo by Ron Galella/WireImage)

Donald Trump attends ‘Hoop-La’ Special Olympics Basketball Game on June 25, 1992 at the Plaza Hotel in New York City.

(Photo by Ron Galella/WireImage)

Donald Trump and Joan Rivers during Opening of The Rose Room in the Plaza Hotel at Plaza Hotel Rose Room in New York City, New York, United States.

(Photo by Ron Galella, Ltd./WireImage)

Donald Trump touches 07 April 1993 Marla Maples stomach to confirm published reports that the actress is pregnant with his child. The two arrived for Maples appearance in the Broadway musical ‘The Will Rogers Follies’.

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US business tycoon Donald Trump enters the PLaza Hotel in New York past supporters 21 December 1994. Hundreds of supporters showed up at a news conference where Trump denied a New York newspaper report that the Sultan of Brunei had bid 300 million USD to buy the Manhattan hotel.

(Photo credit should read DON EMMERT/AFP/Getty Images)

Donald Trump and Christine Whitman during Opening of New Warner Bros. Store in Trump Plaza Casino at Trump Plaza Casino in Atlantic City, New Jersey, United States.

(Photo by Ron Galella/WireImage)

Donald Trump attends Marc Jacobs Fashion Show on April 4, 1995 at the Plaza Hotel in New York City.

(Photo by Ron Galella/WireImage)

New York real estate giant Donald Trump poses in his Trump Tower office on a giant letter ‘T’ on May 8, 1996.

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Portrait of Marla Maples and her husband, businessman Donald Trump, with their daughter Tiffany, as they pose together at the Mar-a-Lago estate, Palm Beach, Florida, 1996.

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Donald Trump and Ron Delsner backstage at a KISS concert at Madison Squre Garden in New York City on July 25, 1996.

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Donald Trump attending Halloween party thrown by Naomi Campbell and Kate Moss at the Supper Club to kick off Fashion Week.  

(Photo by Richard Corkery/NY Daily News via Getty Images)

Donald Trump open his new building at 1 Center Park West- The new Trump International Hotel and Tower.

(Photo byJames Hughes/NY Daily News via Getty Images)

Donald Trump and his girlfriend Celina Midelfar watch Conchita Martinez and Amanda Coetzer 07 September at US Open in Flushing Meadows, NY.

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Celine Dion, husband Rene, Donald Trump Ivanka Trump

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Entrepreneur Donald Trump and Rev. Al Sharpton speak at a ribbon cutting ceremony for Sharpton’s National Action Network Convention April 5, 2002 in New York City. The group aims to further the development of civil rights.

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Donald Trump and his girlfriend Melania Knauss attend the Marc Bouwer/Peta Fall/Winter 2002 Collection show February 14, 2002 during Mercedes-Benz Fashion Week in New York City.

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Donald Trump at Madison Square Garden

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Donald Trump stands on the sidelines before the start of the AFC divisional playoffs between the New England Patriots and Tennessee Titans on January 10, 2004 at Gillette Stadium in Foxboro, Massachusetts. Temperatures have reached as low as 7 degrees in the Foxboro area.

(Photo by Al Bello/Getty Images)

Donald Trump, Visionary Business Leader award honoree, poses with his children Donald Trump Jr. and Ivanka at Fashion Group International’s 22nd Annual ‘Night Of Stars’ at Cipriani’s 42nd Street October 27, 2005 in New York City.

(Photo by Evan Agostini/Getty Images)

Eric Trump and Donald Trump attend the Chicago Bulls vs New Jersey Nets game at the IZOD Center on October 31, 2007 in East Rutherford, New York.

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 Donald Trump delivers a speech with his son Barron after he was honored with the 2,327th star on the Hollywood Walk of Fame on Hollywood Boulevard in Hollywood, CA, 16 January 2007.

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Portrait of former model Melania Trump and her husband, businessman Donald Trump, as they sit together at a table during the 16th annual ‘Lady in Red’ gala, hosted by LIFE (Leaders In Furthering Education), at the Mar-a-Lago club, Palm Beach, Florida, December 4, 2009.

(Photo by Michele Eve Sandberg/Corbis via Getty Images)

Donald Trump sands with Miss Universe 2009 Stefania Fernandez of Venezuela prior to the Miss Universe 2010 Pageant Final at the Mandalay Bay Hotel in Las Vegas on August 23, 2010. Miss Universe is an annual international beauty pageant and along with the Miss World is the most publicized beauty contest in the world. California clothing company Pacific Mills founded the contest 1952 and was acquired by Donald Trump in 1996.

(MARK RALSTON/AFP/Getty Images)

US tycoon Donald Trump arrives to speak at the annual Conservative Political Action Conference (CPAC) at National Harbor, Maryland, outside Washington, on February 27, 2015.

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Donald Trump speaks during the NRA-ILA Leadership Forum at the 2015 NRA Annual Meeting Exhibits on April 10, 2015 in Nashville, Tennessee. The annual NRA meeting and exhibit runs through Sunday.

(Photo by Justin Sullivan/Getty Images)

Real estate mogul and billionaire Donald Trump attends Golf legend Jack Nicklaus’ Congressional Gold Medal ceremony in the U.S. Capitol Rotunda March 24, 2015 in Washington, DC. Trump announed on March 18 that he has launched a presidential exploratory committee.

(Photo by Chip Somodevilla/Getty Images)

Businessman Donald Trump speaks to guests gathered for the Republican Party of Iowa’s Lincoln Dinner at the Iowa Events Center on May 16, 2015 in Des Moines, Iowa. The event sponsored by the Republican Party of Iowa gave several Republican presidential hopefuls an opportunity to strengthen their support among Iowa Republicans ahead of the 2016 Iowa caucus.

(Photo by Scott Olson/Getty Images)

Republican Presidential Candidate Donald Trump visits his Scottish golf course Turnberry with his children Ivanka Trump and Eric Trump on July 30, 2015 in Ayr, Scotland. Donald Trump answered questions from the media at a press conference.

(Photo by Jeff J Mitchell/Getty Images)

U.S. President-elect Donald Trump speaks at his election night rally in Manhattan, New York, U.S., November 9, 2016.

(REUTERS/Carlo Allegri)

Singer Kanye West and President-elect Donald Trump speak with the press after their meetings at Trump Tower December 13, 2016 in New York.

(TIMOTHY A. CLARY/AFP/Getty Images)

Republican U.S. presidential candidate Donald Trump poses for a photo after an interview with Reuters in his office in Trump Tower, in the Manhattan borough of New York City, U.S., May 17, 2016.

(REUTERS/Lucas Jackson)

 Coverage of the 2016 Republican National Convention from the Quicken Loans Arena in Cleveland, Ohio, which airs on all ABC News programs and platforms. On this final night of the convention, Donald Trump accepts the party’s nomination for President of the United States.

(Photo by Ida Mae Astute/ABC via Getty Images) 

U.S. Republican presidential candidate Donald Trump reacts to an answer his wife Melania gives during an interview on NBC’s “Today” show in New York, April 21, 2016.

(REUTERS/Brendan McDermid/File Photo)

President-elect Donald Trump speaks to reporters following his meeting with Jack Ma, Chairman of Alibaba Group, meeting at Trump Tower, January 9, 2017 in New York City. President-elect Donald Trump and his transition team are in the process of filling cabinet and other high level positions for the new administration.

(Photo by Drew Angerer/Getty Images)

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A real go-getter, right? But Trump’s portfolio did not jibe with what I saw each day — which to a surprisingly large extent was him looking at fabric swatches. Indeed, flipping through fabric swatches seemed at times to be his main occupation. Some days he would do it for hours, then take me in what he always called his “French military helicopter” to Atlantic City — where he looked at more fabric swatches or sometimes small samples of wood paneling. It was true that the carpets and drapes at his properties needed to be refreshed frequently, and the seats on the renamed Trump Shuttle required occasional reupholstering. But the main thing about fabric swatches was that they were within his comfort zone — whereas, for example, managing hotels and airlines clearly wasn’t. One of his aides once told me that every room at the Plaza could be filled at the “rack rate” (list price) every night and the revenue still wouldn’t cover the monthly payment of the loan he’d taken out to buy the place. In other words, he’d made a ridiculous deal. Neither he nor the banks had done the math beforehand. Or perhaps Trump knew it, because someone had told him, but didn’t want to think about it. The one thing he is above-average at is compartmentalization.

On days when there were no broadlooms or chenilles to ponder, we would sit around his office and shoot the breeze while (as we now know) out there someplace in the real world, his businesses were hemorrhaging cash. He’d talk about the Yankees, show me pictures of Marla Maples (whom he was then romancing while still married to Ivana) and tell me obviously madeup stories, such as how he had just the other day seen a beautiful, completely naked woman on the street. “Put that in the book!” he’d say, and I’d pretend to write it down.

Occasionally famous people like Bob Hope or America’s Cup captain Dennis Conner came by for no obvious purpose, except that they were paying court and it helped Trump pass the time. Once during a lull I told him a story I thought he’d like to hear, about how I had just taken the Trump Shuttle to Washington, and as we flew through a storm the plane had been struck by lightning.

I commended the pilot for the way he handled the incident; he had gotten on the loudspeaker to tell the passengers what had happened and to reassure them. But instead of being pleased to hear that, Trump, using the general number, immediately dialed the shuttle to demand to know why he hadn’t been informed about what had happened. Unfortunately it took about 10 rings before it was answered by a woman who answered, “Good morning, Trump Shuttle.” By then he was purple with rage. “This … is … Donald … Trump!” he growled. For the poor woman, it must have been like working at Popeye’s and getting a call from the sailor man himself. “Why did it take so long to answer this phone?” Trump demanded. Then, after bawling her out for a minute or two, he hung up abruptly, forgetting why he had called in the first place.

Each day was a string of such nonsensical moments. Once, trying to steer the conversation towards something we could actually use in our book, I asked him about his father. “We haven’t touched on him yet,” I said. “What can you tell me?”

He stared into the middle distance and began to speak. “My father…”

A long pause followed. Then he said, “Charles, put something there. I’ll look at it later.”

Trump’s King Midas period ended in early 1990, when news broke about his looming bankruptcy. At around the same time, Ivana said she was leaving him and Mike Tyson, who had drawn so many people into his Atlantic City hotels, got knocked out by Buster Douglas in Japan. Everything was going to hell. Of course, everything had been going to hell for a a couple of years by then, but now his failure, for the first time, was public, and that made it 100 times worse. That made it real.

In the final weeks of working on the book, we attempted to explain away his disasters, such as the forced sale of his yacht. “As much as I’ve enjoyed it until now,” he (I) wrote, “and as impressive as it’s been to my casino customers, I think I’m giving up the game of who’s got the best boat. … I don’t need it anymore, I don’t want it anymore, and, frankly, I can find better things to do with the money.”

Translation: I’m broke.

He seemed unusually subdued during this period, understandably. One day he told me a sobering story about seeing a homeless person on the street and realizing that man was better off than he was because the homeless man had nothing while he, Trump, had less than zero. Because Trump doesn’t ever walk down the street, would never notice a homeless person if he did and the story involved a degree of introspection, I knew it couldn’t be true and that he was probably parroting something he’d heard someone else say. Still, I included it in the revised introduction.

Let’s just say he didn’t like it. The harsh phone call I got began: “This … is … Donald … Trump.” That’s how I knew he’d built a nicely carpeted compartment around his colossal failures, and moved on.

Charles Leerhsen (@CharlesLeerhsen) is a biographer and historian whose books include “Ty Cobb: A Terrible Beauty.”

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