Original subtitles

[♪]

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.