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PopSugar’s Sarah Siegal writes that in September 1989, New York Magazine published an article titled “Trump vs. Stern: The Unmaking of a Documentary.” The piece described an ongoing battle between then-celebrity businessman Donald Trump and Leonard Stern, a fellow real estate tycoon who owned multiple media outlets — including The Village Voice.

In 1988, Stern financially backed a documentary about Trump. Trump was not happy about it. The two had already exchanged public insults in the past and were considered rivals, but Stern maintained that he did not influence the media companies he owned or the content they created — and that the same went for this project.

The documentary was meant to be the pilot episode in a series about celebrity businessmen in the 1980s, but it never made it to air.

Trump allegedly started to make up rumors that Stern’s wife was calling Trump to beg him for a date and threatened to sue major TV networks if they agreed to carry the documentary. “As we dug into Donald, we learned that he was perhaps the most litigious man in America,” said coproducer Libby Handros. “There was no cable, let alone the internet, so there were only three networks and some independent channels that ran syndicated programming. Given the limited number of outlets, it was sadly very easy for Donald to block the broadcast. All he had to do was threaten to sue anyone who would broadcast the film. Even if his charges had no merits, when someone receives legal papers they have to be answered.”

In other words: why take on the headache?

The documentary languished.

As Trump started getting more involved with politics (and specifically after Trump attacked John McCain in July 2015), Handros decided it was time for the American public to finally see the documentary.

She released it on Aug. 1, 2015. “Our tagline, old Trump, new Trump, same Trump I think says it all,” she said. “In all the years that Donald has been in the spotlight, he is the same person. He has not changed. He still lies, he still cheats small contractors out of money by claiming they did not do a good job, for example.”

According to Handros, “Trump: What’s the Deal” — which is now available on iTunes to rent or buy — is a film that “proves that, far from being an outsider, Donald is the consummate insider. His father, Fred, was politically connected, and those connections propelled Donald forward, and he continued to use them.”


The eye-opening documentary outlines some of the unsavory business decisions and tactics Trump used in New York City during the 1980s and serves as an explanation for his unpopularity in the city.

Read on for some of its most shocking revelations.

1. Trump paid his wife Ivana $1 in salary for running a hotel.

In 1988, Trump bought the Plaza Hotel for $407.5 million. He made his then-wife, Ivana, the president of the hotel. Trump told the press her salary was “$1 a year and all the dresses she could buy.” Later on, he could not afford to pay back the amount of debt the Plaza had acquired, and Citibank agreed to obtain a 49 percent stake in the hotel in exchange for forgiveness of $250 million in debt.

2. Trump lied to the press when Gorbachev visited New York.

When Mikhail Gorbachev, former leader of the Soviet Union, visited the US in 1988, Trump blabbed to TV stations and newspapers that Gorbachev planned to visit Trump Tower. In the film, Newsweek reporter Jonathan Alter commented: “It was almost a textbook example of a publicity stunt, which worked and has worked on many occasions for him.” Not only was this never on the leader’s list of stops, but the visit also did not happen.

3. Trump once sued an architecture critic for a bad review.

After Pulitzer Prize-winning architecture critic Paul Gapp criticized Trump’s plan to build the tallest building in the world in New York, Trump sued for $500 million. Gapp spent a good amount of his article speculating about what the building might look like, since there were no rendering yet for him to judge. Most of his criticism came from the impracticality of the size and shape of the building. He explained that tall, slender buildings are economically inefficient. Eventually, the case was dismissed in Federal District Court in 1985.

4. Trump let people believe he was restoring the Central Park ice skating rink for free.

In 1986, Trump restored the ice skating rink in Central Park. Many New Yorkers were under the impression he did this as a great public service to the city, but in reality, he was paid in full — and his workers weren’t. He told contractors that they were going to work “pro bono,” and understandably, many of them did not understand that this meant working without pay or were unaware that Trump would be paid while they worked for free.

5. Trump landed his first big deal through a series of outsize political favors.

Trump’s first major deal in Manhattan was renovating the rundown Commodore Hotel, which is now known as the Grand Hyatt New York. It was owned by bankrupt Penn Central Railroad, and the owners were desperate to get rid of it. According to the documentary, Hyatt still did not have a New York branch and Trump planned to buy the hotel and get Hyatt to manage it. Trump did not yet have the capital required for the project and had his father, Fred Trump, guarantee part of the construction loan. Through his father’s extensive political ties, he got an enormous, 40-year tax abatement in 1976, which is still the longest ever granted by New York City. The project was approved on the last day of Mayor Beame’s administration.

6. Trump demolished museum-worthy, historic architecture to build Trump Tower.

When Trump built his mecca, he had to tear down a historical New York building, the Bonwit Teller. The building contained priceless architecture, which he promised to gift to the Metropolitan Museum of Art. When he was told how much it would cost to remove the facades from the building in order to preserve them, they were mysteriously demolished.

The Trump Tower is also “missing” ten floors to give the impression that the building is taller than it actually is. He later used this tactic again with his Trump International Hotel and Tower in Columbus Circle; he thought it was more impressive.

It’s also well documented that Trump hired undocumented Polish workers to construct the tower. They slept at the work site and were not given protective gear; many of them were not paid in full either.

7. Trump bought a building in 1981 and then tried to kick out all of the tenants.

In 1981, Trump bought an apartment building located at 100 Central Park South in Manhattan. He reportedly walked in and told everyone in the rent-controlled apartments that they were being evicted and had to leave. According to the tenants interviewed in the documentary, Trump hired people to threaten them into leaving and claimed to be investigating (or lied about) their drinking habits, personal lives, and sexual orientation. He brought eviction lawsuits and lawsuits against the lawyer representing the tenants. Eventually, Trump settled with the tenants’ association in 1986.

8. He destroyed an entire football league.

In 1983, Trump bought the New Jersey Generals, a failing team in the United States Football League (USFL). The USFL had been created as an indirect competitor to the NFL, but the teams played in the Spring instead of the Fall. While the USFL was never as successful as the NFL and infrequently received better ratings than Major League Baseball (aired during the Spring), many saw the league’s potential.

Initially, Trump generated a lot of publicity for the league and helped gain attention and viewership to the USFL. However, Trump wanted to compete directly with the NFL and urged his fellow USFL team owners to move the league to the Fall. According to court transcripts, the goal of this was to either “have a league that’s going to be just as valuable as the NFL, or we’re going to have a merger.”

The NFL already had contracts with the three major TV networks, so the USFL filed an antitrust lawsuit for $1.69 billion. Trump provided the lawyers (including his buddy Roy Cohn).

When the jury finally reached a decision, they sided with the USFL. However, instead of awarding them the fortune they had asked for, they were only awarded $3.75. At this point, the USFL could not hope for a merger and knew they could not compete directly with the NFL. The owners decided to end the USFL in 1986.

9. He’s thought about running for president for a very long time.

The documentary includes footage of an interview with Trump from 1989 on the show 11th Hour. In the clip, the reporter asked Trump if he would ever consider running for president. His response was, “I would much prefer that someone else do it; I just don’t know if somebody else is there. I don’t know if we have the type of advocate that we need. We need major surgery. This country needs major surgery.”

The documentary ends with a somewhat eerie prediction from then-Spy magazine writer Graydon Carter, now the editor of the Trump-maligned Vanity Fair: “The only end to this road is ultimate madness, living alone in an apartment in Panama . . . or taking over the world. One or the other. It’s either the most public life in the world or the most private at the end of this. There’s no in between . . . either the greatest Bond villain of all time or Howard Hughes.”

“Trump: What’s the Deal” is available to rent or buy on iTunes.