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.

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.