All language subtitles for Gangland Chronicles S01E06 1080p WEB h264-EDITH_track3_[eng]

[♪]

Gangs rule their territories
through ruthless enterprises,

fear,

and a strict code.

Deviate from this code

or challenge their power,

and retribution soon follows...

...especially in Boston,

where the streets are ruled
by the Winter Hill Gang.

Rising from a scrappy
neighborhood crew,

the gang becomes the kings

of the city's criminal
underworld...

until one secret dismantles
the entire organization.

Here are three stories from
Boston's infamous Irish gang.

First, a string of arrests
leaves Whitey Bulger

as the last boss
standing in Boston.

It was a huge,
huge power grab.

[Narrator]
Next, an informant finds out

the cost of spilling
the Winter Hill Gang's secrets.

If you were any kind
of threat to them,

they wouldn't hesitate
to kill you.

[Narrator]
And finally, a secret pact

between the gang
and law enforcement

leads to the gang's demise.

This was one
of the darkest moments

in the history of the FBI.

[Narrator] These are stories

from inside
the Winter Hill Gang.

This is Gangland Chronicles.

1972.

Boston.

After a decade of turf wars

between rival
neighborhood Irish gangs,

one crew emerges
as the most powerful...

the Winter Hill Gang.

The roots go back
to Winter Hill,

which was a very much
an Irish Catholic neighborhood

of working-class folks.

They were a very tight group,
very tight knit,

and would always be looking
for ways to make extra money.

[Narrator]
The boss of Winter Hill

is the notorious Howie Winter.

Howie Winter, he had
a reputation of being

a very dangerous individual
that you do not want to cross.

He had a group
of people around him

that were very loyal to him.

[Narrator] Winter Hill's
operation is simple...

shake down anyone else
that's making money.

A lot of their revenue
would come from extorting money

from bookies, drug dealers.

I mean, these were guys

you didn't want
to mess around with.

If they came knocking
on your door asking for money,

chances are if you wanted
to see the next day,

you would pay up.

[Narrator] The gang's interests
in South Boston

are run by Howie Winter's
feared enforcer,

James "Whitey" Bulger.

Whitey Bulger, he grew up in
a working-class Irish family

in a housing project
in South Boston.

He did some time in Alcatraz,

he comes back to Boston,

and it doesn't take long

for him to be back
on the streets again

looking to make money.

Whitey Bulger was somebody

who was doing very well
within the Winter Hill Gang.

He had survived
a lot of internal conflicts...

and ascended to a prominent role
within the organization.

[Narrator]
Fear and intimidation

are a big part of the job
for Whitey Bulger,

and the Winter Hill Gang's
other lieutenant,

Stephen Flemmi.

[Karas] Stevie Flemmi,
they called him the rifleman.

He was a hero
in the Korean War,

and he had a tremendous
penchant for violence.

[Schumacher] Stephen Flemmi was,
you know, kind of

a kindred spirit
with Whitey Bulger.

They both appreciated
the value, in their minds,

of violence.

They were willing to kill,

willing to hurt people
to get what they wanted.

[Narrator] Whitey Bulger
and Stephen Flemmi

both have ambition
beyond working for Howie Winter.

They want all of Boston...

and they're willing
to do anything to take it.

1974.

The Winter Hill Gang focuses
on a new shakedown racket...

fixing horse races.

[Sweeney] The Winter Hill Gang
would threaten, intimidate,

or bribe the jockeys.

They would take a few
of the best horses, right,

and get their jockeys
to hold off on that race,

and then they would bet
on all the other horses.

[Narrator]
Winter Hill isn't just

getting jockeys
to throw the races...

they have the horses
in on it too.

There was one horse
called Spread the Word.

That horse was trained

to, like, do poorly
at all his first races.

The odds changed,

and then Spread The Word
goes in and wins.

Winter Hill made a lot of money
off of that one.

[Narrator] In just over a year,

the Winter Hill Gang
earns $1.5 million,

over 9.5 million today.

It wasn't that sophisticated,
but it was effective.

[Narrator] With operations
at multiple tracks,

the horse racing scam

has been a hands-down winner
for the Winter Hill Gang,

but Howie Winter's gamble
may come back to bite him.

1979. Boston.

The Winter Hill Gang
is making millions

off fixing horse races.

They've gotten away
with it... until now.

After a secret
two-year investigation,

an FBI bust
sweeps up 20 gang members,

including boss Howie Winter,

but there's a surprising
omission.

[Sweeney]
When the indictment came down,

two people were not
on that lengthy list,

and that was Jimmy Bulger
and Stephen Flemmi.

A lot of people were
scratching their heads

at the time.

[Narrator] When Howie Winter
goes down for 10 years,

Whitey Bulger makes his play
to take over as boss.

Whitey said, "This is going
to be my operation."

That doesn't mean to say

everybody wanted
to follow Whitey.

There just really
wasn't a choice.

[Narrator]
While Whitey now controls

Boston's dominant Irish gang,

Winter Hill still comes second

to the powerful
New England Italian Mafia

run by the Angiulo brothers.

[Sweeney] Jerry Angiulo
and his brothers

had a lot of power

and were making a lot of money.

The FBI was on a mission
to take them down.

[Narrator] In 1981,
the FBI does just that,

gutting the New England mafia's
Boston operation.

That opened up
just more opportunities

for Bulger and his associates

to take over
some of their business.

[Narrator]
By 1994, Bulger amasses

a reported $50 million fortune

from extortion
and other rackets.

In a few short years,

Bulger has risen
from street-level enforcer

to the new boss of Boston,

and anyone who defies him
soon finds out

what an unforgiving place
that can be.

1984.

Boston.

The Winter Hill Gang
works with a local fisherman

to smuggle drugs
from South America.

Whitey Bulger also starts using
the fisherman's boats

for a side project...
gun running.

Bulger was proud
of his Irish heritage,

so Bulger was donating arms
to support the IRA,

which is
the Irish Republican army.

The IRA, their goal
is to force Northern Ireland

to ultimately break away
from the United Kingdom.

Bulger likes
what they stand for.

He wants to help them out.

[Narrator] In early September,

a fishing vessel, the Valhalla,

sets sail
for the coast of Ireland

laden with
a million dollars of weapons

that the Winter Hill Gang

intends to donate to the IRA.

[Jarroush] The Valhalla
meets up with another ship,

the Marita Ann,

and the weapons are offloaded
off of Valhalla

onto this new ship...
success story.

But the Marita Ann was seized
by the Irish Navy...

[klaxons wailing]

and the crew was arrested.

The mission was unsuccessful.

[Narrator] The Valhalla makes it
back to Boston Harbor,

where US Customs officials
are waiting.

They search the ship,
but find nothing.

But later, US Customs
and FBI agents

question the ship's engineer,
John McIntyre.

I don't know if he just broke
under pressure or what,

but he quickly just started
talking to police

and wanted to make a deal.

[Jarroush]
Not only is he telling them

stuff about the Valhalla,

but he also talks about another
ship known as the Ramsland,

which was carrying
about 30 tons of marijuana

that Bulger had a stake in.

[Narrator] Customs agents
raid the Ramsland,

seizing the marijuana.

Whitey Bulger's
piece of that shipment

would have been
around $3 million,

roughly $9 million today.

Bulger finds out
somebody's talking,

and when he finds out
that it's McIntyre,

this is when Whitey Bulger

starts to show off
his true colors.

[Sweeney]
The minute Bulger knew,

McIntyre
had a target on his back.

[Narrator] November 30, 1984.

The gang makes a plan
to lure McIntyre

to a vacant house
in South Boston

that Whitey Bulger
has nicknamed "The Haunty."

We named it
the House of Horror, actually,

because of what
was going on in there.

[Narrator]
Just a few months earlier,

Whitey Bulger and Steve Flemmi
murdered a jewel thief

and buried him in the basement

with the help
of a third man, Kevin Weeks.

Bulger, he was
a very calculating individual.

If somebody started getting

a little bit too close
to the organization,

they had to go.

[Narrator] The Winter Hill Gang
tells John McIntyre

there's a party at the Haunty...

but it's an ambush.

Whitey Bulger is waiting.

November 30, 1984.

Boston.

Whitey Bulger lures
informant John McIntyre

to the Winter Hill Gang's
crime house in South Boston,

where he waits
with his lieutenants,

Stephen Flemmi and Kevin Weeks.

[Jarroush]
Whitey Bulger is not a guy

that you ever want to cross.

If you messed up one time,
that's all it took.

[Sweeney] Stephen Flemmi

puts shackles
and handcuffs on McIntyre,

and he's locked to a chair.

Flemmi leans over,
grabs McIntyre's hair,

lifts up his head...

Bulger tries
to strangle him with a rope...

but the rope's too thick,
it's not working.

Bulger then pulls out a gun...

and shoots him
in the back of the head.

[gunfire]

[Narrator] Kevin Weeks
digs a hole to bury the body

while Stephen Flemmi
removes McIntyre's teeth

to obscure his identity.

Whitey Bulger goes upstairs
to take a nap.

I think that kind of speaks

to how Bulger and Flemmi
operated at the time...

very cold, very calculating,

and nothing
was going to stop them

from getting their way.

[Narrator]
Publicly, John McIntyre

is listed as missing,

but law enforcement
quietly fears the worst.

There was a lot of speculation

that word got back
to Bulger and Flemmi

that he was an informant.

I mean, he was
under our protection,

he was cooperating with us,

and yet he was actually
identified as an informant,

resulting in his death.

That's not the way
it's supposed to work.

[Narrator] Revelations of how
the Winter Hill Gang

learned McIntyre was cooperating
with law enforcement,

and much more,

will soon come to light,

sending shockwaves
throughout Boston.

1984.

The FBI has taken down
the Boston boss

of the New England mafia

with great fanfare,

but they seem less interested
in pursuing

the city's new
top criminal organization,

the Winter Hill Gang.

Bulger
and the Winter Hill Gang

were committing murders,

they were stealing,

they were committing
every imaginable crime

that you could think of,

and they were getting away
with it with impunity.

They seemed to be operating
in broad daylight,

yet nobody was
doing anything about it.

[Narrator]
But, out of the public eye,

probes into
Winter Hill Gang activities

by Massachusetts
State Police,

Boston Police, and the DEA

keep hitting
a surprising obstacle.

Every time
they focus an investigation

on Bulger and Flemmi,

it would be compromised.

The FBI was saying,
"No, don't touch them."

[Narrator] Then, in 1990,

the Massachusetts State Police
organized crime unit

launches
an independent investigation

into the Winter Hill Gang.

[Foley] We knew there was
a certain number of bookmakers

that were paying
Bulger and Flemmi directly.

Our feeling was if we were able
to follow the money,

then we'll have an opportunity

to either put wiretaps
or listening devices

into locations
where Bulger and Flemmi are,

and expand our investigation.

[Narrator] The State Police
investigators make progress,

until they are told to share
their information with the FBI.

When I started to do that,
our cases started going south.

[Sweeney] It would seem like
Bulger and Flemmi

kind of were staying
one step ahead,

that they would
know about bugs being placed.

[Narrator] Despite setbacks,
by January 1995,

the Massachusetts State Police
has enough evidence

to indict Whitey Bulger
and Steve Flemmi.

The plan is for the
Massachusetts State Police

to take Flemmi.

The FBI is given the task
to bring in Bulger.

[Foley] We found Flemmi,
we arrested him,

and we told the FBI, "Go forward
with arresting Bulger."

And at that point,
they came back and said,

"We don't have him."

[Narrator] As Whitey Bulger
disappears from Boston,

questions swirl
about how he knew to run.

January 5, 1995. Boston.

Massachusetts State Police

arrest Winter Hill Gang
associate Stephen Flemmi,

but leader James "Whitey" Bulger

has slipped through
the FBI's fingers.

The question is... how?

Some people believed
Bulger was tipped off

that an indictment
would be coming down.

[Narrator] Finally, in 1997,
Stephen Flemmi confirms

how he and Bulger were able

to eliminate
all their competition

and take over Boston...

they've been working
with the FBI.

Flemmi, he went to the judge

and said, "Judge, I can't be
charged with these crimes.

The FBI gave me
the okay to do it,"

but it wasn't until
a year or two later

the FBI admitted

that Bulger and Flemmi
were FBI informers.

[Narrator] Flemmi admits

that their relationship
with the FBI

goes back over 20 years.

They tipped off the FBI
to take down Howie Winter

and the Winter Hill Gang
old guard.

It was a huge,
huge power grab.

[Narrator] And they fed
information to the FBI

on the New England
Italian Mafia's activities.

In exchange, the FBI
left Bulger and Flemmi alone.

[Sweeney]
Suddenly it made sense

how these guys
could have operated

kind of out in the open
for so long.

[Narrator] But the relationship

with John Connolly,
Bulger's FBI handler,

wasn't a one-way street.

Connolly had been receiving
cash payments and gifts

from Whitey Bulger

in exchange for providing him
with tips,

including the identity
of informant John McIntyre.

[gunfire]

They were not controlling
Bulger and Flemmi.

Bulger and Flemmi
were controlling the FBI.

[Narrator] Connolly pays
the price for the corruption.

In 2008, he is convicted
of second-degree murder

for his involvement
in one of the many murders

perpetrated
by the Winter Hill Gang.

The relationship between
FBI agent John Connolly

and Whitey Bulger
and Stephen Flemmi

is really one
of the darkest moments

in the history of the FBI.

[Narrator]
What leads to the gang's rise

is ultimately
what tears it apart.

With Bulger on the run,

the revelations
force gang members

to now fend for themselves.

Jimmy had been a rat.

He had ratted them out.

You know, it was hard
for these men,

because they had been
so in charge and so violent.

They couldn't use their fists
to get out of this,

but they were smart,
and they made deals.

[Narrator] While other
Winter Hill Gang members

serve time for their crimes,

authorities get a break in
the manhunt for Whitey Bulger.

In June of 2011,
authorities are tipped off

that Bulger is living
in this apartment complex

in Santa Monica, California.

[Narrator]
After 16 years at large,

Whitey Bulger is put on trial
for numerous offences.

Members
of the Winter Hill Gang,

including Steve Flemmi,

testify against him.

In 2013, Bulger is found
guilty of 32 charges,

including 11 murders...

and given two consecutive
life sentences.

Five years later, he is moved
from one federal prison

to another in West Virginia.

[Sweeney] Not long
after arriving there,

he was beaten to death
by fellow inmates

who had ties to organized crime.

[Foley] It was payback time
for Whitey,

and I think a lot of people

were okay
with how he left this world.

[Narrator] With most of the
Winter Hill Gang's key players

off the street,

organized crime no longer
has the hold on Boston

as it once did.

[Jarroush] Winter Hill,

despite all of the unbelievably
cruel and brutal things

that they had done

when they were
at the peak of their powers,

kind of becomes a shell
of its former self

and just sort of disintegrates
into the wind.