All language subtitles for Gangland Chronicles - S01E06 - The Winter Hill Gang

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.

A string of arrests leaves Whitey
Bulger as the last boss standing in Boston.

It was a huge, huge power grab.

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.

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.

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 Irish Catholic
neighborhood of working class folks. You know,

they were very tight
group, very tight knit,

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

The boss of Winter Hill is
the notorious Howie Winter.

Howie Winter 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.

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.

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.

He opened 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.

Fear and intimidation are a big
part of the job for Whitey Bulger

and the Winter Hill Gang's
other lieutenant, Stephen Flemmy.

Stevie Flemmy, they called him the
rifleman. He was a hero in the Korean War,

and he had a tremendous
penchant for violence.

Stephen Flemmi was a 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.

Whitey Bulger and Stephen Flemmy 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.

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.

Winterhill 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.

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.

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.

When the indictment came down, two
people were not on that lengthy list,

and that was Jimmy
Bulger and Stephen Fleming.

A lot of people were
scratching their heads at the time.

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.

While Whitey now controls
Boston's dominant Irish gang,

Winterhill still comes second to the
powerful New England Italian mafia.

Run by the Angiolo brothers.

Jerry Angiolo 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.

In 1981, the FBI does just that, cutting
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.

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
fishermen's boats for a side project.

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.

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.

The Valhalla meets up with
another ship, the Merida Anne,

and the weapons are offloaded off
the Valhalla onto this new ship.

Success story.

But the Merida Anne was
seized by the Irish Navy.

And the crew was arrested.

The mission was unsuccessful.

The Valhalla makes it back
to Boston Harbor, where U.S.

customs officials are waiting.

They search the ship, but find nothing.

But later, US Customs and FBI agents
questioned 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.

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.

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.

The minute Bulger knew,
McIntyre had a target on his back.

November 30th, 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.

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.

The Winter Hill Gang
tells John McIntyre there's

a party at the Haunty, but it's an ambush.

Whitey Bulger is waiting.

November 30th, 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 Flemy,

Whitey Bulger is not a guy
that you ever want to cross.

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

Stephen Fleming 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,

shoots him in the back of the head.

Kevin Weeks digs a hole to bury the body,

while Stephen Fleming 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.

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 Flemmy
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.

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 seem to be operating in broad
daylight, yet nobody was doing anything about it.

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 Flemmy,

It would be compromised. The FBI
would say, no, don't touch him.

Then, in 1990, the Massachusetts
State Police Organized Crime Unit

launches an independent
investigation into the Winterhill Gang.

We knew there was
certainly a 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.

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.

It would seem like Bulger and
Flemmi kind of were staying one

step ahead that they would
know about bugs being placed.

Despite setbacks, by January 1995,

the Massachusetts State
Police has enough evidence

to indict Whitey Bulger and Steve Flemmy.

The plan is for the
Massachusetts State Police to take Flemmy.

The FBI is given the
task to bring in Bulger.

We found Flemmy, 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.

As Whitey Bulger disappears from Boston,
questions swirl about how he knew to run.

January 5th, 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.

Finally, in 1997, Stephen Fleming
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 informants.

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.

And they fed information to the FBI on
the New England Italian Mafia's activities.

In exchange, the FBI left
Bulger and Flemmi alone.

Suddenly it made sense
how these guys could have

operated kind of out in
the open for so long.

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.

They were not
controlling Bulger and Flemmi.

Bulger and Flemmi were
controlling the FBI.

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.

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.

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.

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.

After 16 years at large, Whitey Bulger
is put on trial for numerous offenses.

Members of the Winter Hill Gang,
including Steve Flemmy, 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.

Not long after arriving there,

he was beaten to death by fellow
inmates who had ties to organized crime.

It was payback time for Whitey,

and I think a lot of people were
okay with How he left this world.

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.

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.