01x05 - 1987-90: Party's Over

[bunniefuu]

New York City.

Happy new year!

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

[Newsreader] Boom times,
that's what the markets 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 in 1987,
the boom times came to a halt.

And with the party over,
the backlash began.

A wall street cheat
found his reputation in ruins.

[Newsreader] Boesky admitted
to profiting from insider trading.

And decided
he wouldn't go down alone.

Boesky ratted out everybody.

A hotel queen faced
a city full of angry subjects.

And I hope she gets everything
that comes to her.

And a future behind bars.

She had been indicted
on a great many counts.

I'm innocent.

A gilded gangster continued
to taunt the feds.

He was just out there,
thumbing his nose at law enforcement.

Even as he handed them
a smoking g*n.

Tape recorded conversations were a
gold mine for the FBI, they were a jackpot.

And while a politically minded
prosecutor pounced on them all...

Giuliani earned this reputation
as this law and order person.

If you violate the law,
you go to prison.

A developer from queens
kept pushing his luck.

Eventually, word started to get
out. It was time to take him down.

It was a toxic wind
that was ripe to blow up.

He said, "I wish you could see her naked."
Even today, it makes me uncomfortable.

These five titans would reshape
the city and the world we live in today.

But as the 90s neared,
they'd finally face their day of reckoning.

- Are you surprised?
- No comment.

And empires would fall.

We are very honorable people.

[Shouting]

Black Monday, October 19th, 1987 when
the stock market went into a free fall.

Today's precipitous plunge struck
fear in the hearts and pocket books

of even wall street veterans.

The market is now
down 221 points.

Does that make you nervous?

No, I died already.

Black Monday was the inflection
point at which all of a sudden

the party screeched to a halt.

[Newsreader] In trading rooms
on wall street there was panic.

Sell orders flooded in from big
institutional investors,

from private investors.
From mutual funds.

A bull market that had gone on
too far and too long

without enough corrections
suddenly just went down.

[Newsreader] The largest
drop in stock market

history,
falling 508 points on the dow.

It was this absolutely terrifying event
where the market was plummeting

and it didn't feel
like it would ever stop.

[Newsreader] More
than 604 million shares

changed hands with the
decline of 22.6 percent

far greater than the single-day loss of


Panic, complete panic.
Everyone's going crazy.

What happens when everybody tries
to leave the room at the same time?

Well, nobody can get out. And
that's the 1987 crash in a nutshell.

There were moments where Washington
bureaucrats believed that not only

wall street but the American
economy could melt down.

The chastening that everybody who
went through black Monday went through.

There was a new
found caution that it

instilled in everybody
I knew on wall street.

We'd now seen what was possible when
the confetti years suddenly turned dark.

It was a devastating blow to
public confidence in the markets.

But it wasn't the first. For months, a
drum beat of revelations had cast a shadow

on wall street. Starting with the
spectacular collapse of an arbitrager.

[Newsreader] Ivan Boesky came to
the us district court today

squeezed
into a Japanese compact car.

He's already paid 100 million in
penalties for insider trading violations,

is barred from the
securities industry for

life, disbarred, and,
his lawyer says, broke.

[Sorkin] The Boesky story represented this
rags-to-riches guy who came from nothing

who rode the wall street wave.
He became emblematic

of what wall street was in the


his success in people's faces 'cause
he was so out there with his success,

he was so public about his success.
When he came undone, the lips curled.

People smiled.
The schadenfreude was thick.

[Inaudible]

[Stewart] When Boesky agreed
to plead guilty,

he knew he's be sentenced
to some kind of prison term.

Depending on the value
of his cooperation.

[Madrick] Boesky decided
to cooperate 'cause

he didn't think he had
any way to fight it out.

He was guilty and he wanted
to save his a*s.

[Newsreader] Boesky faces up to five
years in prison and a fine of $250,000.

It had been a remarkable run
for the kid from Detroit.

But now he knew it had come
to an end.

And if he had to end other careers
to minimize the fallout, well, so be it.

So Boesky ratted out everybody.

[Newsreader] All over the us, people
have been shocked by scenes like this.

Investment banker Martin
Siegel ducking reporters

after pleading guilty
to insider trading.

[Stewart] Siegel said always felt
guilty for feeding information to Boesky

and now Martin Siegel is over and
Boesky was at the heart of the case

of securities law violations
against Michael milken.

He was the center
of this information hub.

That's the most powerful position
you can possible be on in wall street.

[Newsreader] He was
worth more than a billion

dollars when he got
caught cooking the books.

[Stewart] Michael milken eventually
pleaded guilty to six felonies

and agreed to pay


[Guiliani] Mr. Boesky has been
extremely valuable, without his cooperation

there would be people who would be involved
in ongoing fraudulent transactions.

While the arbitrager downfall destroyed
the careers of those around him,

it bolstered the career of one
cunning prosecutor who made the most

of every white collar crook
he could cuff.

[Newsreader] Since 1984 there have
been more than 48 cases of insider trading,

many involving the financial community,
brought

by New York's us attorney,
Rudolph giuliani.

They're seen usually as very shrewd,
very capable, very industrious.

Yet there's this whole
other side to their life

in which they are cheating
and lying and stealing.

Which they keep secret.

[Kirtzman] Rudy
giuliani wanted to be the

center of attention and
to give enormous power

to ruin people's lives. There was a
famous case of giuliani going after traders

at kidder peabody
and handcuffing them

and marching them
across the trading room floor.

How much did you make
from your inside information?

[Mahler] A perp walk
is the idea of arresting

people in this very public
and almost theatrical way

marching them out of offices so that the
news cameras would capture these guys.

Do you think the others are
doing the same thing you are?

[Mahler] Publicly
parading these wall street

millionaires,
as if they were common criminals

it was intended to be a form of deterrence,
look what'll happen if you break the law.

But you could just as easily
argue that he was showboating.

Everything was kind
of a PR campaign for giuliani.

He's busting these guys,
he's locking 'em up, he's indicting them.

He did that on purpose and it enhanced
his reputation as the sheriff of New York.

Part of the criticism was, "well,
those are decent white collar guys."

"They, they, and white guys,
to boot. They shouldn't be subjected"

"to this kind of thing that actual
criminals are subjected to."

I, I thought,
"no, this is good."

[Stewart] To this day there are
people on wall street who criticize him

but the American people needed to
see these people being held accountable,

that these very wealthy, so-called masters
of the universe were not above the law.

They committed crimes. Why not go
after 'em? Why not go after the big fish?

All this profligate behavior started to
begin to move very much out of vogue.

The so-called
"masters of the universe"

were trading their penthouses
for prison cells.

Once the heroes of the decade,
they were now its villains.

Anyone who embodied these areas of
New York City power, giuliani took aim at.

If you violate the law, whether
it's insider trading or tax evasion,

or fraud or bribery,
and so-called "white collar crime,"

the overwhelming general rule
is that you go to prison.

As the disgraced
trader awaited his

sentencing,
the prosecutor savored his victory.

But not for long because he'd already
set his sights on an even juicier target.

It is now alleged that they did
not pay millions of dollars in taxes.

[Newsreader] Us attorney Rudolph giuliani
said if the helmsleys are found guilty,

they will serve some jail time.

It was the late 80s in New York
and the cultural tide was turning.

For years, some of the city's elite
had treated their wealth and fame

as a license
to act with impunity.

But now the public was growing tired of
their antics and a hard-driving prosecutor

was capitalizing
on their outrage,

going after the formerly
untouchable with a vengeance.

[Newsreader] Former miss america
and New York City official Bess myerson

is facing a possible 30 years in prison
and a half a million dollars in fines.

We prosecute
all sorts of people.

Little people,
in-between people,

and some of the wealthiest
billionaires in the United States.

And there was no better target
among New York's high society

than the queen of real estate, who
had been outed as a tax cheat in the press.

She might have been a scapegoat
for the greed and excess of the 80s,

but she brought it on herself.

The helmlseys, one of the world's
wealthiest couples, were indicted

in New York today on state and
federal charges involving a tax scam.

She was an easy target.
So imperious, so mean.

[Inaudible]

Leona Helmsley was supposed
to have impeccable taste,

you'd expect to have
impeccable morals and she didn't.

New yorkers had loved her
as the queen who stood guard,

tending to her customers'
every whim.

But a queen who defrauded the
government and stiffed her contractors?

That they found
far less charming.

[Newsreader] Harry and Leona are in trouble
because they spent millions of dollars

on renovations
at their Connecticut estate.

Twenty-nine acres,


charged it to their
businesses for deductions.

[Plaskin] She was allegedly
deducting personal expenses

as business expenses
or expenses for her hotels.

[Feldshuh] She was indicted on one count
of conspiracy to defraud the United States.

Three counts of tax evasion, three
counts of falsifying personal tax returns.

Ten counts of mail fraud. She had
been indicted on a great many counts.

[Newsreader] The feds also allege that Mrs.
Helmsley extorted money from suppliers,

demanded and received kickbacks
in exchange for Helmsley business.

Well, you wouldn't call her cheap.
You would call her tight. She thought that,

"I'm paying him a lot of money,
why won't he

do this for me for next
to nothing or nothing?"

I confronted her, I said, "is it true that,
you know, you didn't pay contractors"

"or you tried to get services
for free?"

She said, "well, the bill
that he gave me was too high."

She started talking about feeling
victimized by the government.

After all, she paid millions
of dollars in taxes.

She didn't think she did anything
wrong and she stuck to that.

It isn't fair. It isn't fair.
Plus I look like [inaudible]

It was clear from the
beginning that Leona

Helmsley was not
interested in pleading guilty.

I have done nothing wrong.

[Plaskin] By the time she went to trial,
she was so famous and so notorious,

it would have been almost
impossible to find a jury of her peers

who didn't have that image of her
that had been painted in the press.

Harry and Leona helmlsey are
so rich they could practically start

their own country and if they did
they wouldn't have to pay taxes,

since it appears that they're
not too fond of them anyway.

[Newsreader] Leona
Helmsley made an understated

entrance to court no Lima,
no husband Harry.

[Dowling] The story was that he was no
longer mentally able to go through a trial.

But I think what actually
happened was Harry had done

so many favors for every judge,
every official

that they were not about to prosecute their
friend for something that his wife did.

[Feldshuh] Leona helmlsey
hired Gerald feffer to defend her.

He took an unorthodox point of view
that he had hoped would save her.

[Devita] What he actually said
in opening statement is,

"you may hear that Leona
Helmsley is a tough b*tch."

"It's not a crime
to be a tough b*tch."

Feldshuh he tried to prove that you cannot
send a person to prison just for being

a tough b*tch,
just for not liking them, just

for thinking that they
were imperialistic.

These were oversights that she
didn't know what was going on,

that she was more
concerned with dust in the

corner than she was
with her accounting firm.

Did we steal somebody's money?

Oh, the government
says you stole theirs.

Did they prove it?

[Newsreader] Prosecution called 44
witnesses, many of them former employees

who described Leona
as greedy and arrogant.

Everybody who was around her
knew what a terror she was.

And that always catches up
with people. And it did.

[Newsreader] Former employees testified
about doctored invoices for everything

from Louis xvi furniture
to carrots and potatoes.

You could see that she was
unhappy at some of the testimony.

Certainly, there must be
one person in this entire world

that would say I'm a decent
person. They didn't bring anyone in.

[Silverstein] The coup
de grâce was when her

housekeeper testified
that Leona had said,

"only little people pay taxes."
So everybody hated her after that.

I sat down with a housemaid?

And said, "let's have tea?"
Or where was it?

In the bedroom, what? And I said, "do
you know only the little people pay taxes?"

Does this make sense to intelligent
people? Huh? This story was concocted.

And contrived. And boy did that
make the newspapers, didn't it?

"Paying taxes is for the little
people." Wow, such a great line.

It'll be on her gravestone,
it probably is on her gravestone, actually.

"Rip taxes are
for the little people."

"Only the little people pay
taxes." That was her against us.

We were the downtrodden,
poor, misunderstood public

and she was the big bad wolf.

Sooner or later you
gotta pay the Piper and

I hope she gets everything
that comes to her.

It's poor, middle class
who have to pay taxes.

But the little people don't just
pay taxes. They sit on juries too.

And they were about to hand the queen
of mean a verdict that would seal her fate.

Ms. Helmsley, do you have any
response to these allegations at all?

While a day of reckoning had
arrived for some New York titans

who'd overplayed their hands,
others continued to push their luck.

By the late 1980s, Donald Trump
was building seemingly everywhere.

And buying seemingly everything.

[Newsreader] He already owns trump tower,
trump Plaza, trump park, and trump castle.

He bought the eastern shuttle
and renamed it trump shuttle.

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.

All of these things were not money
makers. So they added to his overall debt.

[Kruse] The banks continued
to give him more money.

The press he received
largely was uncritical.

He was living
this consequence-free existence.

So there was no reason for him
to dial back his behavior.

By 1988, the striver from queens
had become a national celebrity.

And his thirst for attention was leading
him to make one bold move after another.

But there were certain things
he wasn't sharing with the press.

And it was those
that would threaten to undo him.

It's gonna be fancier than ever.
The Plaza hotel is getting a face lift

and the new owners, the trumps,
reveal their ambitious plans today.

The purchase of the Plaza hotel for
$400 million was simply a trophy purchase.

And using junk bond, high interest
rate financing, just complicated it more.

I think that Donald thought that
he was capable of pulling this off.

You know, I, I think
he was delusional.

The first thing that he did
was announce to the world

that he was making Ivana trump
the president of the Plaza hotel

and that he was going to pay her
in dresses.

That she could have as many dresses,
buy as many dresses as she wants.

I thought the greatest
toy that I could give

Ivana would be to put
her at the Plaza hotel.

[Kruse] When she started running the Plaza,
this created friction.

He was Donald Trump
but she was Ivana trump.

She was becoming a character
in her own right.

Donald was so intent
on building his empire

and Ivana was sort of
a piece in the empire.

She was a beautiful,
smart woman who could fit into his life.

A lot of women in your position would
feel overshadowed by their husband.

- Do you ever feel that?
- Not at all. Not at all.

[Brown] I think people forget what a
big figure Ivana trump was in the 80s.

I mean, we did as many pieces about
Ivana as we did about the Donald.

Of course Ivana and he together
were the ultimate glitzy duo

who were out every night
and who you could not miss.

She and he shared a certain
aesthetic sensibility of blond and gold

and cosmeticized
to within an inch of her life.

[Res] I always thought Ivana would
do whatever he asked her to do.

It was always about pleasing him
and impressing him.

[O'Donnell] She absolutely
worshiped Donald

trump but they had a
business relationship too

now all of us that ran these properties
had screaming matches with Donald.

And she did as well. She was not a
pushover and anybody that suggests

that she was just didn't know,
you know,

really how smart and how
tough Ivana trump was.

Is there anything
you wouldn't support you man in?

Oh sure. [Laughs] Oh sure. I
wouldn't support him a few things.

I wouldn't support if Donald would
be running around and fooling around.

You know,
that I couldn't live with.

I used to say to her, "Ivana, you know,
you better keep your eye on the ball here"

"because, you know, Donald is young,
handsome, and now very rich and powerful."

[O'Donnell] I did see Donald talk publicly
about Ivana in a way that he hadn't done

up to that time. It was more negative,
more jokingly, putting her down.

And he talked about
how women were after

him. "This one wants me,
that one wants me."

[Fox] He loved beautiful women and he
loves something that would stroke his ego.

Trump had spent his entire life
believing he can get away with anything.

[Inaudible]

As I was writing the art of the deal,
it wasn't clear to me

that he was simultaneously
carrying on an affair.

[Evans] Every year there was an American
booksellers association convention.

This particular year was going
to be in Las Vegas. Donald said,

"hey, let's just go out
in my plane."

What fun. His plane was
set up like a living room.

It was very glamorous,
lots of velvet.

And just as we land and are getting
our things together, a door opens.

A door to, I think a bedroom
or something.

All along, a stowaway,
Marla maples, comes out.

She's been on the plane with us the
entire time. I am so shocked, it's like,

I don't know, the Scarlet letter or
something right in front of me of like,

"oh." it was such a scandal, you cannot
imagine. Everybody's mouth dropped.

[O'Donnell] Marla maples was a fun loving,
"let's have a party" kind of woman.

Ivana and Marla
were polar opposites.

[Fox] Marla maples
grew up in Georgia,

she was definitely a southern
belle and Georgia peach.

She was someone who competed and
won the miss Hawaiian tropic pageant.

[O'Donnell] Donald Trump just saw
beauty in her and I think he saw youth.

He loved that image so much
of being with a younger woman.

One time at a dinner, he said,
"I wish you could see her naked."

And I was... I just cringed. Even today it
makes me, it makes me uncomfortable.

[Fox] Marla was a struggling,
young model.

Each opportunity that you find
can be so instrumental in your future.

She had nothing and needed him. And
I think he loved that need to be needed.

- My wife Ivana, who's accepted...
- [Applause]

[Fox] Eventually, word started to get out
that Donald was dating another woman.

And I don't think she wanted
to believe it was true,

no one wants to believe that
about their husband.

[Carswell] Ivana knew that
Donald liked blond, busty women.

So she went to California to meet
with Michael Jackson's plastic surgeon.

And she comes back,
she no longer looked like Ivana trump.

I do remember saying to him, "Donald,
look at what Ivana is doing for you."

"I mean, she's completely
changed every part of her."

And he disdained what she was
doing. He was never going back to her.

[O'Donnell] Common
sense would tell you

that this is not gonna
be a secret for long.

And so we were waiting
for the blow up.

[Evans] And then all of a sudden the
tabloids start churning these stories out

on Marla maples, Marla with Donald,
Ivana, the whole triangle.

[O'Donnell] I think Donald was very
shocked by the publicity that he got.

But he also loved it but he believes
this philosophy of all press is good press.

He believed if you handle it in a
certain way, you can get away with it.

And the affair was not the only big
gamble he was making at the time.

At the end of the decade,
the brash developer

embarked on his
biggest project yet.

Donald Trump today opened the
doors to his billion dollar gamble,

his new Atlantic city
casino, the Taj Mahal.

Financed entirely through debt,
the Taj Mahal would need to earn

over one million
dollars a day to stay

afloat. An amount no
casino had ever raked in.

[O'Donnell] I thought that the taj
mahal was gonna be in desperate shape.

The red flags were up
prior to the deal being done.

[Johnston] After Donald Trump gets control
of the Taj Mahal, he can't pay his bills.

And it was all Donald's reality running
up against the hard numbers of banking.

[O'Donnell] It really
was only a matter of time

before this stuff was
gonna catch up with him.

He was hiding too many things for
there not to be a day of reckoning.

His deals were crumbling. Eventually
they're gonna catch up with the scam.

[Newsreader] Donald Trump, the

larger-than-life new
York developer celebrity.

Could it be that he's built
his empire on 90 percent ego?

The headlines are
screaming "death of a legend,"

calling him the
has-been of high finance.

It was time to take him down.

[Newsreader] It was a monster parade,
even by New York standards.

The police say more
than 2 millions people

jammed to lower
Manhattan to cheer the mets.

In October of 1986,
the mets' legendary world series victory

over the Boston Red Sox
united new yorkers in celebration.

[Deveney] The mets really
should have been a dynasty

and perhaps should have won
multiple world series.

They had these young players,
Darryl strawberry, Dwight gooden.

But on the day of the parade

in which the mets were
celebrating the 1986 world series,

Dwight gooden is in queens in
a housing project, high on coke

and watching the parade
on TV because he's

still so high on coke
he hasn't left the room.

The mets were never the same
after that.

A drug epidemic that had been
ravaging the city didn't spare the mets.

And down the road
from shea stadium in queens,

an even deadlier threat was emerging.
Hitting low-income communities hard.

[Mcdaniels] I grew up in queens,
New York, which was like the suburbs.

We wasn't rich but people
would mow their lawn.

And the kids would play in the
sprinklers and ride their big wheels.

You had the candy
store. You had the

delicatessen. You had
the real estate office.

In the 80s, I came back to my neighborhood
and everybody started looking different.

My friend's sister, who was the
sexiest girl in the neighborhood,

came looking like someone out "the walking
dead." It was a plague when crack came.

[Newsreader] Purveyors
of the drug cocaine are

now selling it in its
purest form called crack.

Much of the nation's crack
problem is concentrated in New York.

Crack is basically just cocaine
with a couple of ingredients added

and you throw it in the
microwave.

It is what they call "the instant
high." Once you ingest it, you're done.

That high that you
would get off that freebase

would make all your
troubles fade away.

[Deveney] That high only lasts
about 15 minutes.

When you get through those 15 minutes,
you're gonna need more.

[Interviewee] You're speeding
like 100 miles an hour.

And when the mind is going that fast,
it's just normal for you to become violent.

People were out of their minds,
literally.

You go through such a low when
you're out and you can't get any more

that you're ready to k*ll.

I remember one case,

this young man had m*rder*d
his mother for money to buy crack.

This was going on
all over the city.

[Weatherspoon] People sold
their souls to not live in their reality.

[Newsreader] Crack is cocaine
marketed to a lower-income people.

It's a very, very cheaply made drug.
You could buy it for five bucks at a time.

[Weatherspoon] Jobs disappear. Housing
goes down the tube. Schools are not good.

And then you bring
in the drugs and the

hustle to make a dollar.
And you get it going.

[Chanting] We want our buildings back,
no more crime, no more crack.

They have to take a stand,
just like we're doing.

If they wanna get these drugs out of the
neighborhood, they've got to take a stand.

[Weatherspoon] You have decent
people living in poor neighborhoods.

That's where they can afford
to live.

While those involved in the drug trade
are surrounding them and smothering them.

This has reached
epidemic portions.

[Guilianni] I don't think we
incapacitate drug dealers.

We do not put them
away for long enough

periods of time to
really make a difference.

As soon as crack becomes a high profile
problem, giuliani instantly seizes on it.

We do not give 40-
and 50-year prison

sentences that put the
major drug dealers away.

[Byfield] Giuliani earned this
reputation as this law-and-order person.

"The w*r on drugs." He took
that up as a part of his mantle.

We will prosecute the biggest drug cases,
the medium-sized drug cases,

and the street drug cases in areas where
the local courts for one reason or another

aren't able to deliver
a deterrent effect.

[Mahler] As us attorney, giuliani
decided to demand stricter sentences

for low-level drug dealers.

In most cases, these low-level
drug dealers were people of color.

The prosecutor's crusade for stricter
federal sentences largely impacted

the city's poorer
communities. With mandatory

five-year prison terms
for dealers and users.

[Newsreader] Narcotics police
in northern Manhattan

arrest small time dealers
almost every night.

While crack is being used
in poorer communities,

the people who are using
the powdered version of cocaine

all across wealthy communities are not
demonized in the press in the same way.

The fear that was generated
around crack allowed huge disparities

in arrests, prosecutions,
sentencing.

Crack cocaine would get
you a ten-year sentence

while cocaine
might get you probation.

[Byfield] People didn't think twice
about the lengthening of sentencing

and police abuse of power
in fighting the drug problem.

[Newsreader] This
is called operation

pressure point. Local
police make the arrests

and turn the suspects over to us
attorney Giuliani's staff for prosecution.

I take on things that nobody
else has ever taken on

and I accomplish things that
others haven't accomplished.

While the prosecutor's tough
stance played well in the press,

his harsh policies devastated
neighborhood after neighborhood.

Angering many people
in those communities.

And it wouldn't be long before
they made their voices heard.

By the late 1980s, homicide rates
had hit record highs in New York City

and pressure was mounting
to curb the violence.

And despite major blows
to organized crime,

the us attorney's office had yet
to catch public enemy number one.

John Gotti understood
power and strength.

[Gabriel] It was important for him to
show everyone he was an invincible boss.

You just didn't wanna cross him.
To his own people, he was ruthless.

He was a tough guy and
he wasn't afraid of anything.

He truly believed that
nobody would ever convict him.

The FBI had been hunting the new
godfather since he knocked off his boss.

And so far, he'd escaped
every trap they'd set.

They knew they had to find
a new approach and fast.

[Newsreader] Gotti has been
tried and tailed for five years now.

In that time never convicted
of a crime. Outfoxing the foxes

in a big stakes game of cops and robbers
that has made Gotti kind of a legend.

[Gabriel] The government
couldn't get him.

So by the time he gets
acquittal number two,

he's becoming this folk hero
even to the mob.

His third acquittal,
people are now even more fearful of the mob

because, god, you can't even put this guy
in jail, everyone knows he k*lled the boss,

he's doing all this stuff,
you can't touch him.

He was just out there and almost
thumbing his nose at law enforcement.

[Mouw] He became a magical
figure in the city of New York.

[Gabriel] Everybody was pulling
for John Gotti.

They've dismissed
how bad of a guy he was.

[Newsreader] Gotti is somewhat
of a local hero here.

A lot of people said, "boy,
you're never gonna catch him."

"You will never get this guy, he's
untouchable. He's beaten all these cases."

And it just created a sort of,
almost a frenzy within law enforcement

to try and make a
case on him. And at that

point,
we had already been investigating Gotti

the FBI felt it needed
taped conversations.

[Mouw] Our goal was to find out where
John conducts his criminal activities

and put a microphone there
and record all the conversations.

And it quickly became apparent
that John established his headquarters

at the old ravenite social club,


And after a few months
we are able to pick up a pattern

where he was coming there
four to five nights a week.

[Newsreader] On the northern end
of little Italy, a brick façade

has replaced a wooden store
front. It is the ravenite social club.

And more importantly for us,
all the captains of the Gambino family

were summoned to meet him there.

So every night you'd have four
or five captains, 30 or 40 soldiers,

the associates in
this club or outside the

club. Which is a godsend
for law enforcement.

[McDonald] We were up doing physical
surveillance and listening to devices

for a period of about eight months,
struggling to get audible conversations.

There's just a lot of people in a
small room, all talking at the same time.

We were getting bits and pieces that led
us to understand we were in the right place

but nothing
we could indict with.

And a lot of people this time said, "you're
wasting your time, you'll never get him."

In the summer of '89
we finally got a nice break.

The FBI found out that Gotti
was using an apartment two stories

above the ravenite social club to
discuss important family business.

[Mouw] We found out that they're using
an apartment up there owned by this widow

named Mrs. Cirelli,
whose husband used to be a Gambino soldier,

Mike cirelli,
used to run the club.

[Capeci] One particular weekend,
when the widow was out of town,

the FBI got in and they put
a bug in her apartment.

[McDonald] We had a location
to observe comings and goings

and we were tape recording
conversations.

[Mouw] We hear him clomping
up the stairs.

We hear the front
door open. John Gotti is

deaf in his left ear so
they had to talk loud.

[Capeci] The FBI captured Gotti

admitting to voluminous organized
crime activity as well as murders.

Tape recorded conversations
were a gold mine

for the FBI. They
were a jackpot for them.

[Gabriel] Very much to our surprise,
we hear John on a diatribe

about why he k*lled Paul
Castellano. He starts the conversation,

"when that guy Paul got sick."
That was Paul died.

You know, here we are,
several years after

they k*lled this guy,
it was astonishing to us.

Fortunately for law enforcement,
Gotti supplied many smoking g*ns

through his own words. He was
intercepted taking about, you know,

ordering the executions of people, saying
that he was responsible for their murders.

The smoking g*n
was Gotti himself.

Just by listening to the tapes that we had,
we knew we had a case that was solid,

the game was over.
The end was near.

January, 1989. New York City.

A blunt spoken prosecutor with boundless
ambition had felled giant after giant.

And now the end game
was in sight.

Crime buster, us attorney Rudolph
giuliani announced that he is stepping down

at the end of this month. He
didn't say why but many believe

that he will be a republican
candidate for mayor of New York City.

Giuliani was probably
the most effective us attorney

for the southern district
in history.

During his years as us attorney,
he really changed the nature of the office

so that it became
much more aggressive.

Rudy takes down
all of the big villains of

New York City, you know,
a cast of bad guys.

The prosecutor had been hounding
the mafia for years

and the last domino to fall
would be the dapper Don himself.

[Newsreader] John Gotti, the reputed
boss of the nation's largest mafia family

was arrested tonight along with
his top three associates

in a move by the FBI to crush
the Gambino crime family.

We decided to arrest him
at the ravenite.

And I walked down there later, it was
like shock and awe right after, you know,

bombing attack, 'cause there are
like 20 Gambino guys in there.

And they're all sitting out there smoking,
looking around. They were amazed.

The greatest fear was that John Gotti got
arrested. These are like the untouchables.

In many respects, I have to say
the guy was a very good wise guy.

But what draws against that is the
fact that he did everything so publicly,

made so many stupid mistakes and
really brought down the Gambino family.

So where he was a good wise guy,
he wasn't good at how he ex*cuted it.

[Newsreader] Arrested
with Gotti tonight

was his under boss
Sammy "the bull" gravano,

his consigliere, or family advisor,
frank locascio.

And one of his top capos
or captains, Tommy Gambino.

If he beats this massive federal
case brought on by the FBI,

it could make him the biggest gangster
in america since the legendary al Capone.

If he loses, it's likely Gotti will
spend the rest of his life in jail.

And just as he chased gangsters in queens,
the prosecutor also took aim

at traders in Manhattan. His biggest
catch? The king of arbitrage himself.

Picture this.
Ivan Boesky jail bird.

[Guiliani] The three-year
sentence given by judge lasker

gives the real world of what
happens in criminal proceedings

and in federal courts around
this country. A heavy sentence.

Mr. Boesky accepts
the court's decision.

He now must pick up the remnants

and try to get on
with the business of living

a constructive and useful life.

For Boesky to go from master of the
universe to a prisoner, surely humbled him.

I think surely it depressed him.

Ivan Boesky, who was used to earning more
than a million dollars in a single day,

will now be paid 11 cents an
hour for his work at the prison.

Ivan Boesky spent a couple of years
at a low security prison out in California.

You go, you do your time and with luck,
you know, no one shivs you.

He got shamed. He's not a guy who's
gonna be celebrated in gossip columns.

He's gonna be, guy's gonna walk down
the street and people are gonna whisper,

"hey, that's Ivan Boesky.
That's the guy who went to jail."

He's got a Scarlet letter
on his head.

But people are capable
of having second acts.

And there was the queen of the
palace herself, prosecuted for tax fraud.

Many embittered associates
testified against her

but in the end, it was her own
words that would truly seal her fate.

Leona's line that only the little
people pay taxes resonated so much

after this exhausting decade

of the big shots getting richer
while others were not.

Here was a perfect expression
of the ruling class.

She has a reputation that is a
woman who really has no scruples.

Greed will do you in and I guess
that's what they, motto that they live by.

After a two-month trial,
a jury found her guilty.

[Devita] Leona Helmsley was
convicted of income tax evasion.

She was convicted of aiding, assisting
in the filing of false tax returns.

She was convicted of
mail fraud in connection

with her New York
state income tax returns.

[Feldshuh] She stepped over bodies to
make sure she had her marble dance floor.

And that was her downfall.

She was brought to account
for her misdeeds.

[Newsreader] Many new yorkers
consider her the personification of greed.

Leona Helmsley had become
a symbol of excess and of greed

and of just how money can
just make someone awful.

Leona Helmsley was so awful that even
Donald Trump took pleasure in her fall.

Harry would never fire him,
he's... [inaudible]

Perhaps unsurprisingly,
she immediately planned an appeal.

I have done nothing wrong. I'm innocent.
My only crime is that I'm Leona Helmsley.

As the decade's icons
faced a day of reckoning,

the former sheriff of New York
moved to seize control of the whole city.

[Announcer] The man who's
gonna be our next mayor,

who's gonna give the city of new
York back its soul, Rudy giuliani.

[Applause]

[Kirtzman] In New York there's
no greater stage than mayor.

The mayor is the center
of the tabloid's focus.

New York is a city overwhelmed
by crime, crack, and corruption.

There was a sense the New York
was out of control and giuliani,

his whole thing is control. And so it
was a natural office for him to run for.

Now is the time to take our city back
from the violent criminals on the streets

and the white collar criminals
in their office suites.

Coming in as a hard lying guy,
the cops are

backing him,
the days are numbered for that.

The candidate's years of combative tactics
would lead to his own day of reckoning

when he faced his toughest opponent
yet: The citizens of New York City.

Before the night is over, new
yorkers will either elect David denkins,

the first black mayor
of New York City history,

or one-time us attorney
Rudolph giuliani

will become the first
republican mayor in 20 years.

For a person who had
mastered the New York media,

Giuliani's mayoral run
was a total disaster.