Empires of New York (2020) – S01E06 – Legacy of the ’80s: Greed Is Still Good [Transcript]

Set amid the grit, greed, and glory of 1980s New York, Empires of New York chronicles the meteoric rise of five icons - Ivan Boesky, Donald Trump, Leona Helmsley, Rudy Giuliani and John Gotti.
Empires of New York (2020)

Set amid the grit, greed and glory of 1980s New York, Empires of New York chronicles the meteoric rise of five icons who not only reshaped the city but contributed mightily to the world we live in today: Donald Trump, Ivan Boesky, Leona Helmsley, John Gotti and Rudy Giuliani. Drawing on exclusive interviews, never-before-told stories and secret tapes, the series follows titans of the era who shared a singular trait: the insatiable need to win at all costs. Seizing opportunity in an era jolted by one cultural upheaval after another – MTV and 24-hour news, hip hop, drugs, the onset of AIDS – they broke rules, flaunted their wealth and delighted in the destruction of their enemies. And oddly, at times America came to love them for it.



New York City.

Happy New Year!

At the dawn of the ’80s, it was exploding with opportunity.

[newsreader] Boom times. That’s what the numbers signal today, an economy that’s on a roll in this country. A place to seek money, power, fame. Amid the glitz and greed, five titans seized their moment. But by the end of the decade, that moment had passed and we’d put greed behind us for good. Or had we?

The President of the United States.

A hot-shot developer was dodging questions about soaring debt…

Trump, the cash crunch.

…and scandalous behavior.

Well, she’s a fantastic woman, but I won’t say anymore.

But the tabloids that helped make him were about to take him down.

You have a lot of very dishonest reporters, in my opinion.

A hard-charging prosecutor had become a candidate for mayor.

The word impossible is just not in my vocabulary.

But some in the city were growing tired of his crusades.

The people of our town don’t want a prosecutor, they want a mayor.

A celebrity don was back on trial, feeding a media frenzy.

The Gotti trial is the hottest show off Broadway.

And when the verdict was read…

The Teflon is gone, the don is covered with Velcro.

[newsreader] Hundreds of Gotti supporters, outraged by that sentence, tried to storm the Brooklyn courthouse.

And while the former king of Wall Street was finally headed for jail, the Queen of Mean was mounting a last-ditch effort to remain a free woman.

Not guilty, not guilty. I am innocent.

That was it. I’m gonna take you out, you’re gonna take me out. This isn’t gonna end well.

I’ve never seen anybody so heartbroken in my life. She was devastated.

There was almost a daily feeling of how crazy this is.

These larger than life figures would forever change our idea of success…

My new game is Trump, the Game.

…and excess…

Forty-two million.

…and though, at the end of the 80s, we may have delighted in their downfall…

[woman] These are card-carrying, crashing egotists.

…our celebration of their values was just beginning.

[interviewer] But you have said that if you ran for president, you’d win.

I think I’d have a very good chance.

[dramatic music playing]

Okay! [applause] He’s a man who is strong, smart, he’s done very well for himself, for an ex Chippendale dancer. I’ve… oh!


A man who, five minutes after he got here, tried to buy our studio. So, who is this famous billionaire?

[audience] Donald Trump!

He was the man with the Midas touch. Builder of golden towers, high-rolling casino operator, bestselling author, myth maker of epic proportions.

How rich are you, just basically?


Right now?

Well, it depends on which magazine you read.

I mean, how much you got in your wallet? I wanna see–

He was also sitting on a mountain of debt and an explosive personal secret. But with every breathless news report, his legend only grew, until it really did seem like his potential was limitless.

[Emily Fox] He had his buildings, he had his hotels. He presented himself, as he does now, as a man who was incredibly financially successful.

Privately, his businesses were having more trouble than he would let on.

He was a guy who thought he was invincible, from a business standpoint and also from a personal standpoint.

And he gets the idea in his head that he should be running everything.

[newsreader] Trump has said, quite seriously, that he’s a good enough bargainer to negotiate a nuclear disarmament treaty with the Russians.

[David Cay Johnston] Donald first publicly talked about being president in 1987. He knew all he had to do was keep pressing ahead and he would have a shot at it.

You have said that, if you ran for president, you’d win.

I think I’d have a very good chance. I mean, I like to win.

[Michael Kruse] Roger Stone, a long-time political operative, called him a “prime piece of political horse flesh.” It was his idea for Trump to go to Portsmouth, New Hampshire, where he gave a talk at a Rotary Club and created quite a stir.

This country is being taken such advantage of, we need strength. I mean, you think Gorbachev is tough. Think of this character Khomeini. [laughter] I mean, this son of a bitch is something like nobody’s ever seen!

[Barbara Res] Trump wanted to create the notion that he was so competent, that he was so great at what he did that he could do the hardest, most important job in the world and that’s being president.

I love the country, but I think you’re gonna have probably George Bush as your next president. He’s an excellent guy, an excellent man, he’s a friend of mine and I’m here for that reason.

That was not a serious idea in the late 80s, but it planted a seed that this guy, a developer in New York, a celebrity, the author of The Art of the Deal, would be trafficking in political ideas. He was laying groundwork for what we would see decades later.

Good luck, everyone. Thank you all for being here.

[Kurt Andersen] Donald Trump had delusions of grandeur from the get-go. At the same time, big, legitimate banks enabled Donald Trump. They kept giving him money.

[Charles Bagli] Donald is already starting to file tax returns that would indicate he was losing money, not making money.

[newsreader] Is Donald Trump in financial trouble? Some in the financial community are looking for signs that Trump may be trying to raise cash because of a current, or anticipated shortage, caused by heavy debt.

But in the meantime, there was a constant flow of money from Wall Street and from investors. So, when the opportunity came to grab a hold of the biggest, most luxurious casino in Atlantic City, The Taj Mahal, he took it.

Donald Trump today opened the doors to his billion-dollar gamble, his new Atlantic City casino, The Taj Mahal.

[Bagli] It had been under construction for several years, it was way over budget, but it was supposed to dominate the whole Atlantic City gambling scene.

[newsreader] The Taj Mahal stretches out over 17 acres along the boardwalk. There’s glitz and glitter galore, $15 million worth of chandeliers and 1200 luxury hotel rooms.

[Johnston] He buys it with entirely borrowed money, junk bonds $675, million at 14% interest. He’s got over a quarter million dollar a day bill just for interest on the bonds and close to another million dollars a day to pay all the other bills of running the place and of course, paying out the few winners that were out there.

Johnston Trump executives insist they can make a million dollars a day the experts say they’ll need just to pay for the casino.

And that is something that had never happened at any casino, anywhere in the world at that point. So, it was not just ambitious, it was stupid.

I do have a risk, I do have a financial risk, but I have also a reputation risk and that’s very important to me.

[Johnston] From day one, there are hundreds of contractors and vendors who were delivering goods to him and he’s not paying them, because he doesn’t have the income to support all the borrowing he’s done. And then the day came when Donald couldn’t pay the monthly payments on his debt and it’s very clear that this is going to collapse.

There was almost a daily feeling of how crazy this is.

So, a million dollars a day, while it sounds like a lot of money, for the building that we’re talking about, it should be very easily made.

We realized that Donald was uncontrollable.

[dramatic music playing]

[Giuliani] New York is a city overwhelmed by crime, crack, and corruption. [man] New York City, 1989.

The fear in our streets, parks, and subways all point to a city that is out of control!

He was the avenging US attorney with an audacious crime busting record and he was now closer than ever to his ultimate goal of winning political office. With crime rates surging in 1989, no one seemed better suited to become New York City’s next mayor.

From a policing perspective, it’s a very violent era. This was a very constant topic of conversation, the level of violence in the city.

[Kirtzman] Giuliani ran as the law-and-order candidate and New York needed more law and order.

As mayor, I will lead the battle to take our streets back, hearts back, subways back from the criminals.

He saw this as an opportunity to clean up the city.

[newsreader] Giuliani remains a major threat to Koch’s chances for a fourth term, assuming the mayor survives the Democratic primary, particularly the challenge from David Dinkins.

[Kirtzman] David Dinkins had risen though the ranks to become Manhattan borough president, a somewhat powerful job.

[Ken Auletta] During the primary race relations were very tender and Dinkins came in as someone who might be a healer.

I felt the rise of David Dinkins in the context of a series of racial events through the age. The Michael Stewart incident… there was the Eleanor Bumpurs incident… The Howard Beach incident.

The victims were three black men whose car had broken down.

[Gil Troy] The crime problem, all too often in New York, is seen as a racial problem, but it’s the incidents where blacks and whites interact that generate the headlines, that generate the tensions.

A Wall Street investment banker remains unconscious in very critical condition tonight after a brutal attack while she was jogging in Central Park.

The Central Park jogger case turned into one of the biggest rape cases we have ever seen in New York City. A young, white woman was beaten badly, raped, and left for dead.

[newsreader] Today, police arrested four juveniles, ages 14 through 15, all charged with attempted murder and rape.

Black and Latino kids… Whatever the police and the prosecutors said was accepted as fact.

The horrifying crime has sparked a new call for the death penalty, this one from billionaire developer, Donald Trump.

[Byfield] Donald Trump takes out an ad in all the major newspapers, calling for the death penalty, before there’s been a trial!

There’s not a thing in the world wrong with hating in certain instances and you have an instance here where you have killers roaming the street, preying on all of us.

He said what he said in that ad and then he doubled down in a variety of other places. He gave license to think those things about those kids, who didn’t do it.

Amid this atmosphere of racial tension, comes the murder of Yusef Hawkins in Bensonhurst.

[newsreader] Police say 30 white teenagers armed with baseball bats and at least one gun, attacked Hawkins and his three companions.

This confrontation leads to him being shot to death.

[newsreader] In the aftermath of the killing, racial tensions in Bensonhurst and New York City have mounted.

It rocks the city.

[crowd chanting] Bensonhurst! Bensonhurst! This is not Johannesburg!

There are not racists in this community.

This is not a racist community, we just don’t like black people, that’s all.

People were feeling as if the city was reaching a point of ungovernability.

It’s not enough for people to be angry. If you don’t have somebody bring a change in policy and procedures, we’ll never get ahead.

Koch was perceived more and more as a divisive figure, and that David Dinkins might be the solution to this.

In the minds of many, we weren’t supposed to win but nobody told us that.

After 12 years leading the city of New York, Ed Koch will no longer be mayor. Instead, David Dinkins, the president of the borough of Manhattan, is in a position to become the first black mayor of the nation’s largest city.

You gave me your votes and even more, in a tough time, you gave me your trust.

This year, Dinkins faces strong opposition from former US Attorney Rudolph Giuliani.

On the day I become mayor, the old political system that is dragging this city down is out!

Two candidates were left to battle it out for the mayor’s seat. One, a seasoned politician with a message of harmony and justice.

The other, a righteous ex-lawman with a message of crime and punishment. Emphasis on the punishment.

Giuliani was a US attorney coming in as a hard-line guy. It’s not about being the nice guy, it’s about being the tough guy.

[Kirtzman] For a person who had mastered the New York media, Giuliani didn’t have his message together. He had people making all these allegations relating to the character of Dinkins. It was clear that Giuliani would stoop to low levels to get elected.

Why does David Dinkins always wait until he gets caught? Rudy Giuliani: experience, integrity, and nobody owns him.

Rudy was a tough campaigner, but we were pretty good also.

I think the people of our town don’t want a prosecutor, they want a mayor.

[Guiliani] Well, wait, wait a second. I think the people of this town want a mayor who has nothing to fear from a prosecutor.

I think it became an issue of who could really keep the city under control and they both were running with different philosophies.

The people do not want a city divided against itself.

New York is a city overwhelmed by crime.

What can unite us is far stronger than the forces that can keep us apart. [applause]

Who can reduce crime better?

I know how he feels. I come from a background of people that have been excluded.

Who can get the drug problem under control better?

I propose to be mayor of all of the people.

Take our city back.

Mayor of all the people.

The word impossible is just not in my vocabulary.

We owe it to our children not to give up, give in, or turn back.

Biggest of all American cities has a black mayor, David Dinkins.

Dinkins beat republican Rudolph Giuliani tonight.

David Dinkins’ message of racial harmony was the key to that race. It wasn’t the time for a prosecutor, it was the time for harmony.

In the end, it was one of the closest mayoral elections in the history of New York.

It was close. You win by one vote, you’re still the winner.

I’ve just spoken to Major-Elect David Dinkins.

[crowd booing]

No! No! No! No! Quiet! Quiet!!

Simply put, this was David Dinkins’ time.

In the days ahead, I will meet with him and I will reach out to the many others across this city.

[Kirtzman] In many ways, Giuliani’s run for mayor was an embarrassment. This was a person who had a very, very strong reputation.

After the loss to Dinkins, he says that the election was stolen from him because a lot of blacks and Puerto Ricans voted illegally in the outer boroughs. There’s no evidence, but one of the defining characteristics of Rudy Giuliani is vindictiveness, is a desire to avenge any kind of defeat. And you can see that in 1989. One of the fascinating things about the Giuliani story is that it was always hard to tell, on any given day, whether this was a good man or an evil man.

Through the lens of that time, you would have said he saw wrong doing and was determined to punish it and halt it by any means necessary. I think you might look back and decide maybe he is a man who really, in some ways, is no different than the people he prosecuted. He just had different tools in which to exercise his will to power.

In the totality of Giuliani’s career, there was too much good and bad.

[journalist] Morning, Mr. Gotti. What about all this news of more indictments? You think the government’s gonna frame you?

You guys [inaudible].

Throughout the late 80s, New York’s most notorious gangster had captivated the nation by strutting for cameras and skillfully dodging law enforcement.

But, in 1990, the feds had snagged him again and this time they had his own words to use against him.

Secret FBI tapes of reputed mob boss, John Gotti, reveal the dark and violent world of the Gambino crime family.

[newsreader] Most of the discussions took place in an apartment two floors above Gotti’s Ravenite social club in Little Italy, an apartment that Gotti had no idea was bugged by the FBI. Clearly, the man Gotti considers his closest ally, according to the tapes, is this man, Sam “Sammy the Bull” Gravano.

About a year or so before we take them off the street, John Gotti made Sammy the underboss of the family. Sammy had the reputation of being a shooter and a killer. So, he made sure that kind of stuff got done for John Gotti.

Right now, Gotti and Gravano were both behind bars together, awaiting trial, and Sammy Bull had had listened to some of the tapes.

They got the tapes, ’cause they get to listen to the evidence that the government’s gonna present, and Sammy started hearing what John was saying in some of the conversations that he wasn’t part of.

Gotti’s bad-mouthing Gravano, Sammy’s turning red, he just wants to burst.

Gotti was basically blaming him for all the murders that he was authorizing.

That was it. He and John were now on the outs and, you know, I’m gonna take you out, you’re gonna take me out. This isn’t gonna end well. And that’s what, you know, put it in his head that he needed to find another way out.

He pricks your finger.

[man] Who? Who?

The Godfather.

[newsreader] Since Jo Valachi became the first sworn member of La Cosa Nostra to break the code of silence, only a small handful of low-level hoods have chosen to follow in violating that sacred code of omertà .

Well, the most significant rule in the mafia, the rule that enabled them to prevail and to succeed for as long as they did, was the rule of omertà , that is silence. You can’t rat anyone out. If you’re caught, you go and do your time, you keep your mouth shut.

Just now Sammy “The Bull” Gravano listened to the tapes. He knew that his goose was cooked.

Sammy Bull got the sense that he could get himself a good deal.

Sammy sent word that he wanted to speak to us. We had to go to the jail to take him out.

[McDonald] So, they bring down Sammy, he gets in the car and we drive to a safe house. I asked Sammy, says, “Tell us about the Castellano body murder.” “Okay.” So he just went from A to Z. I remember drawing a little map showing East 46th Street. “I was here with John. You’re the shooters,” you do the whole thing.

He heard the tapes, he said, “Everything’s accurate on it. I mean, you guys have us dead to rights, but, you know, he put me in those five murders and I’m gonna do life for it.” He said, “And you guys, I can trust you more than I can trust the mob.” He says, “I wanna join Team America.” John found out within that night, word got to him Sammy had been pulled out and he knew it was over, just died inside.

[newsreader] Sammy “The Bull” Gravano has been transferred out of a federal prison and is reportedly talking to prosecutors–

[newsreader 2] John Gotti’s closest ally, facing 50 years in prison, has joined the ranks of the squealers.

The decision by Sammy Gravano to testify is certainly a big, big event. He knows where all the bodies are buried.

Every news organization in the city was covering it. People inside, people outside the courthouse, people watching, people who came. It was a huge thing.

In New York, the Gotti trial is the hottest show off Broadway with spectators lining up as early as two in the morning, waiting hours for a chance to get inside the courtroom.

Mickey Rourke showed up, Anthony Quinn showed up.

This is one of the great dramas that’s going on today.

A lot of people showed up to express their, you know, concern and allegiance with poor John Gotti, who was being fingered by Sammy Gravano, the rat.

The trial of reputed mob leader, John Gotti, has begun in New York City.

[Gabriel] When Sammy came out, you could have cut the air with a knife. I mean, it just… the two of them stared each other down. I still think John probably felt sicker than Sammy.

If looks could kill, there were two people who would be falling down dead. He was a great witness. John Gotti barked, I bit. He owned up to the crimes he committed and he fingered John Gotti for the murders that he authorized and running the crime family in his image. He nailed him, you know, to the cross.

Good morning, everybody. Mob boss, John Gotti, is facing life in prison after being convicted of all 13 counts against him.

The jury concluded that he was responsible for murdering five associates in the Gambino crime family and was guilty of racketeering charges.

[Capeci] When the verdict came in, he just sat there. He tried to keep a stiff upper lip, but he knew that he was dead in the water, convicted, and gonna go to jail for the rest of his life.

The Teflon has gone. The don is covered with Velcro and every charge in the indictment stuck.

Outside, hundreds of Gotti supporters, outraged by that sentence, tried to storm the Brooklyn courthouse.

The immediate reaction was a bunch of lunatics went down to the courthouse and started overturning cars. And people started screaming, “Free John Gotti.”

John Gotti took power of the mob at the right time.

He was someone who was out there when the media was looking for a godfather.

[Andersen] There was a kind of nostalgia aspect to John Gotti becoming this famous figure in the 80s. Mafiosi were regarded as high-stakes entertainment figures. They could kill each other, they could become famous, they wear fancy suits and be on television all the time. And like, they’re not gonna kill me, they’re not gonna kill my children, so, like, fine.

[Gabriel] I think John was a product of what was going on in the 80s. The page six stuff was becoming big. Just being recognized on any platform was significant and he fed into that. I mean, it consumed him.

[McDonald] I don’t know what Gotti was thinking because nobody ever gets away with it. Eventually, they’re gonna get caught, unless they just die in their own beds. But I guess he enjoyed his run while he had it. All that acclaim and notoriety and attention. Something that he craved.

Whatever power the mafia had, it’s gone. The mafia would never be the same once John Gotti was put in charge and then once he goes away.

Been a big week on Wall Street all this week. Many of the rich and famous now are not as rich and some are infamous.

By 1990, the stock market may have recovered from the crash of ’87, but the verdict was in. Greed was no longer good.

These are card-carrying, crashing egotists.

The heroes of the 1980s had become villains right before our eyes.

[newsreader] Another fallen mogul with a big ego, Ivan Boesky. He bribed people to give him inside information and made millions.

[Auletta] Ivan Boesky, he’s not a guy who’s gonna be on a magazine cover ever again. But he did it. We’re not doing it to him, he did it, and therefore should pay a price.

[newsreader] Boesky served his time, grew a beard, and was last seen testifying against a former friend in court.

Ivan Boesky, or Dennis Levine, or some of the other perpetrators, they were pariahs.

[Madrick] Ivan Boesky was a tragic figure, partly because he had talents. He was very disciplined, he worked very hard, but in the end, the lesson of New York in the 80s is, greed wins out.

As fate set in and former masters of the universe were shamed by the city that once worshiped them, one wasn’t giving up without a fight.

Harry and Leona Helmsley, one of the world’s wealthiest couples, are charged tonight with cheating on their income taxes.

Accompanied by her husband, Harry, who wasn’t well enough to stand trial, and pushing her way through a mob of photographers, Leona Helmsley arrives to learn her sentence.

Hang ’em by the toes. [laughs]

I think she should be given the maximum.

[Devita] Leona Helmsley was convicted of income tax evasion and aiding and assisting in the preparation of false tax returns. She was also found guilty for mail fraud relating to the New York state income tax return.

[newsreader] Leona Helmsley won’t go to prison right away. She left court with her husband, free on bail to prepare an appeal.

I’ve done nothing wrong. I have done nothing wrong.

Leona Helmsley felt she was innocent.

I’m innocent.

And that she was indicted only because “I’m Leona Helmsley.”

That had she been a man in business, she clearly would have walked or been elected president.

Once she was indicted, Leona Helmsley hired Gerald Feffer to defend her. He did not win the case. Of course, he went from being her hero to being some awful person, so she replaced him with Alan Dershowitz.

[newsreader] Power defense attorney, Alan Dershowitz, has promised to take her case all the way to the Supreme Court if necessary.

The joke is over! We’re talking about putting a 71-year-old woman with an ailing husband in jail! Enough is enough!

We will file our brief in three weeks and we will approve and assert…

We will win.

…total innocence.

At the urging of her new attorney, the Queen of Mean embarked on a media tour to rehabilitate her public image… or at least let them know how unfairly she’d been treated.

I got a $25 million bail. There’s a man in Milwaukee that chops up people and eats them. Revolting story. He got a million dollar’s bail.

I’ve done nothing and look what they have done to us.

I did not do anything.

Not guilty, not guilty, not guilty. I am innocent.

Why she was going on television was to gain sympathy, but you have to first apologize, which she never did.

Leona blamed everybody for her own problems. She blamed the prosecutor, Rudolph Giuliani.

…is out to get you, Leona?

Oh yes. Mr Giuliani, there is no question about it. I was a great stepping stone for him.

[Bagli] She blamed the ad company that developed the whole “Queen of the Hotels.” I think, for those that were more steeped in Leonaism, it was the perfect expression. The Queen of the Mean, because she was such an unloving personality.

She was, in the perception of society, gratuitously cruel. She really defined the archetypal paranoid bully. And that was her downfall.

[newsreader] She’s 71, she’s given millions to charity. Her husband is gravely ill and she’s on her way to prison.

[Plaskin] She paid a seven million dollar fine, she was convicted to four years in jail, and 250 hours of community service.

[newsreader] The judge has ordered her to begin serving her four-year tax evasion sentence, ironically, on April 15, tax day.

[singing] Everything we’ve heard about her is absolutely vile. From the testimony tit-bits from her terrible trial. But her reign of terror is over, ’cause Leona’s going to, yes, any day, she’s going to– Leona’s going to jail!

I wonder what Trump’s game, is this time?

Mr. Trump! Mr. Trump, Mr. Trump. Mr. Trump, please.

My new game is Trump, the Game.

Trump, the Game. It’s not whether you win or lose, it’s whether you win.


I think you’ll like it.

For years, the developer turned super star had been tempting fate in matters both professional and personal, and now they were coming to a head. In Atlantic City, his casinos were teetering on the edge, while his marriage was on equally shaky ground.

By the late 80s, he wants more and more and more in terms of objects, totems of wealth. But he also wants somebody else.

[newsreader] We think that’s her on the right, or at least Donald Trump brought a woman who looks a lot like Marla to a party thrown by Ted Tuner in 1988.

[Kruse] He was stowing Marla Maples in his casinos, in his hotels. Eventually this would all come to light.

The chatter is getting louder and louder and louder. Then the story broke.

One of the nation’s most publicly married couples is heading for a very public divorce.

He was accused of consorting with an attractive young woman named Marla Maples. Lurid newspaper headlines made much of that.

There is really nothing more Trumpian than the way their divorce played out. And it was all dished out and eaten up by the tabloids.

Marla Maples saying, “The best sex I ever had.” If that was said about most human beings, they would not get out of bed that day. Donald Trump glorified in it. He said, “This is wonderful!”

Well, she’s a fantastic woman, but I won’t say any more on that. We’re here to cover a boxing match.

I mean, Ivana was… I’ve never seen anybody so heartbroken in my life as she was. She was devastated.

Poor thing!

[newsreader] Some people think this first celebrity divorce of the 90s is something serious being turned into a circus.

No matter who it is, separations are sad.

Ultimately, I think Ivana won. She was this sympathetic figure who had been wronged by her husband who was bragging about his affair with another woman. It was not the best look for him. It was sort of the moment where he lost control of his ability to dictate what the narrative would be and that irked him more than just about anything.

You have a lot of very dishonest reporters, in my opinion. And I mean dishonest. I’m not talking about they’re slightly off, I mean they are totally dishonest, where they’ll report things knowingly that they’re wrong.

It is this demarcation point when we learn that Trump’s gonna get divorced and Trump actually is probably not nearly as rich as we thought. Stuff starts to unravel pretty quickly for Trump in 1990.

[Johnston] He can’t pay the interest payments on The Taj Mahal, his newest casino. The Trump Shuttle collapses. He can’t run the Plaza Hotel in New York that he grossly overpaid for.

Within months, this was not a viable enterprise.

[newsreader] Donald could even lose the dome of his new gambling casino, The Taj Mahal. He hasn’t finished paying for it and there’s talk that the contractor might repossess it.

[newsreader 2] The Trump Organization, one of the glitziest companies in America, confirmed today that it is in meetings with bankers in an attempt to reorganize its vast debt.

Over 1000 lawyers were working on this case. A thousand lawyers trying to sort out Donald Trump’s finances.

The New Jersey Casino Control Commission has unanimously approved Donald Trump’s bail out plan. That plan allows him to use his three Atlantic City casinos as collateral for a $65 million loan.

He borrowed so brazenly that he was, in effect, too big to fail. The banks did not let him go down.

The banks can’t afford to let him go broke. Katie, they would go broke, so they’ve got to let The Donald be The Donald.

After casino regulators approved Donald Trump’s out-of-court corporate bankruptcy that he doesn’t wanna call bankruptcy, what does he do? He walks out in front of the cameras and goes, this is a great day for Donald Trump. This is a huge victory.

We had a great victory, I’m as happy as hell. Thank you very much.

[Johnston] Well, you know what? It was! He didn’t have to pay people back and he walked away a wealthy man, leaving all this damage behind him.

His empire is saved, at least temporarily. But his public image ain’t what it used to be.

[Carswell] After he was exposed, it was time for America not to take him as seriously as we once did in the 1980s.

[Auletta] There was a good reason to think, by the early 90s, that Donald Trump’s time had passed. He’s not the success he claims to be, it was over.

He was not in exile, exactly, but considered to be a little bit closer to a clown. He was just a guy who was famous and had crazy hair.

[singing] Green Acres is the place to be. Farm living is the life for me!

Mr. and Mrs. Donald Trump.

Donald Trump would show up sort of randomly in cameos in television shows, in movies. And in one of the Home Alone sequels, all of a sudden there’s Donald Trump.

Excuse me, where’s the lobby?

Down the hall and to the left.


[Kruse] Anything to keep himself going.

You know, when people ask me, “Well, what are his virtues?” Indefatigable…

[announcer] Hey, look at this! Donald Trump! Donald Trump! [laughs]

[Schwartz] …relentless.

[announcer] The hostile take-over of Donald Trump!

Here he was, last man standing, and that was the story that he told. And pretty soon, people forgot about all the problems.

[Kruse] The most important thing Donald Trump learned was not to change his ways. It was not to be more responsible with money. It was, “I can’t be killed, I’m too big to fail.” In spite of all the excesses of the 80s, he survived in the 90s because of those excesses. What a take-away.

Those of us old enough to remember the 1970s, when we wander around New York today, we drive our children crazy. It used to be so dirty! It used to be so dangerous. It used to be decaying. And all of a sudden it’s as if Cinderella’s fairy god mother came and eliminated crime and eliminated grime and made towers grow and made a city that looked like it was on its way to becoming the ash heap of history into the next great center of civilization. And yet, those things come with a cost. And New York City not only symbolizes all the great that occurred in the 1980s, but the underlying hangover from the 1980s.

[Sorkin] In the 80s, the idea of the American dream was transported. It became an individual dream. It was about individual success and individual power. And we didn’t, unfortunately, care enough about how they attained that success and how they attained that wealth.

The American dream actually is very deceiving.

The self-flattering idea of America is a place where you play by the rules and you’re industrious, you’ll do well. Well, here are all these people who became unreasonably, fabulously, financially successful by breaking the rules.

You will lie, you will cheat, you will steal, you will back-stab ’cause doing it the right way takes too long.

[newsreader] Money. Who’s got it? Is there an unelected elite that rules our town?

[Mahler] In the moment, it may seem as though it was just a temporary change, that America kind of lost its mind for a few years there in the 1980s.

That all these people got their comeuppance. Whether it’s Ivan Boesky, who became a pariah, Donald Trump, whose company went bankrupt before, of course, reinventing himself, Leona Helmsley, who becomes a figure of total ridicule, John Gotti, who finally gets nailed, and Rudy Giuliani, who was ruthlessly ambitious, who lost his first mayoral race in 1989. What seemed like kind of a fleeting moment is in fact a defining moment because the legacy of those years are what we are living with now. This obsession with wealth, with celebrity. This sort of turning away from the idea that it’s part of your job as a citizen to take care of other people.

Today, there is so much anger spilled about the Kardashians and Instagram influencers, how they have corrupted society, how these people don’t deserve to be successful. It’s all based on nothing and based on a lie. But what we’re seeing today, it started in New York in the 80s by people who were also making up their own realities, exaggerating their own successes. Greedy in a way that we had never seen before and willing to do whatever it took in order to propagate these myths.

Wall Street, it’s still fueled by the greed, by fear, by testosterone. And so we can sit here and talk about Ivan Boesky and Michael Milkin and young people beside the TV can say, “Who the heck are those guys?” Well, the same guys that are working on Wall Street today, it’s all the same. It’s all the same, just different names.

[James B. Stewart] And, we had another huge round of insider trading scandals, again, in the 2000s. There is something about it, about the risk-free potential to make so much money, that some people just find irresistible.

[Sorkin] I think, today, we see the underbelly of it. We see that so much of it was about smoke and mirrors, was a house of cards. And I think that’s been a real punch to the gut for a lot of people.

[crowd chanting] We want the 99 percent!

[newsreader] Hundreds have occupied Wall Street. Protesters gathered–

[crowd chanting] I can’t breathe! I can’t breathe!

[newsreader] People spilling into the streets, their message underscored with star power.

[Troy] There’s so much anger and so much alienation and so much fear and so much partisanship. That great disconnect of today is rooted in the 1980s. It’s rooted in the high and the low. It’s rooted in the great excess that also meant that we no longer judged ourselves by normal standards, by our neighbor’s standards, but by celebrity standards, and it came at the cost of our souls. So, as we wander around New York City in the 21st century, we start seeing symbols of the American Dream with an asterisk, the American Dream tarnished, the American Dream at what cost?




[Rudolph Giuliani] No, it isn’t truth. Truth isn’t truth.


[Donald Trump] I, Donald John Trump, do solemnly swear–



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