♪♪
Narrator: In the criminal underworld...
Good evening, Mr. Gotti.
...power is a prize worth killing for.
[ Gunshots ]
Have none, and you're a nobody.
Reporter: A car bomb killed one man.
Narrator: Have some, and you'll always crave more.
[ Gunfire ]
[ Siren wails ]
Out here, kings aren't born.
They're made.
And only a few have what it takes to climb to the top.
♪♪
In 1980s Boston, one of the most ruthless gangsters in history
rises to rule the city ‐‐
James "Whitey" Bulger.
He controls his empire
through fear and blood,
killing anyone who stands in his way.
It was a chess game to him,
and he was just 10 moves in front of everybody.
Narrator: But years before Whitey becomes the boss,
he's just a low‐level enforcer with something to prove,
a foot soldier in a small‐time gang war
that's about to kick off...
and unleash the most feared criminal mastermind
in the Northeast.
[ Gunshots ]
This is the story of how a criminal becomes a kingpin.
♪♪
[ Tires screech ]
♪♪
♪ Yeah ♪
♪ Yeah, yeah, yeah, yeah ♪
♪ Yeaaaaaaah ♪
Boom!
In South Boston,
survival depends on the code of the streets.
It's kill or be killed.
♪♪
[ Man screams ]
And when Kenny Killeen bites the nose off Mickey Dwyer,
a rival gang member, it's a declaration of war.
[ Men cheering ]
The gangs that run Boston's South Side ‐‐
the Killeens and the Mullens ‐‐ are enemies fighting for turf.
Prepare for war, boys!
[ Men cheering ]
But over the next 10 years,
what begins as a battle for one neighborhood
escalates into a war for Boston itself.
A powder keg in a city that's already burning.
Boston had been down economically
for a number of years.
Narrator: Working‐class South Boston,
known to its residents as "Southie,"
is one of the areas hardest hit by the downturn.
The largely white Irish‐American population
is already on the edge when a federal court orders
Boston public schools to de‐segregate
by forced busing.
The reaction is swift and violent
as racial tensions boil over in Southie.
The middle class pretty much decamped out of the city.
All the people that were left were down and out of all races,
and there was less opposition
to the criminal element in those days.
Narrator: Across the city,
the crime rate doubles in just five years.
I was offered a job at the high school breaking up fights.
Narrator: Kevin Weeks is a native of Southie
and a former associate of Whitey Bulger.
The only problem was that I had just graduated,
so a lot of the students up there were friends of mine.
So instead of breaking up the fights,
I was actually jumping in on the fights.
Narrator: The chaos in Boston is an opportunity
for the one industry where it's still possible
to make a living ‐‐
the underworld, where drugs, prostitution,
and gambling fuel
a business worth hundreds of millions of dollars a year.
But in Boston, no one crew runs it all.
Cullen: Throughout the history of organized crime
in the 20th century,
Boston was unusual in the sense
that if you went to other big East Coast cities,
the Mafia, la Cosa Nostra,
would have been the natural dominant organized crime figure.
They had a national organization.
Narrator: But in Boston,
the Italian Mafia sticks to one area ‐‐
the North End.
The Italians, they had an area,
and they had a territory,
and ‐‐ and that was it and really nobody infringed upon it.
Narrator: The rest of the city is Irish.
But for generations, the Irish had been unable
to take control of the underworld.
Cullen: The Irish, just by sheer numbers,
should have been the dominant organized‐crime group.
But they weren't because the Irish gangsters in Boston
went by neighborhoods.
Those groups would always be fighting with each other,
and the Irish gangsters would be killing Irish gangsters.
Carr: The Irish just decimate one another.
Life magazine actually did a huge spread in 1967
of all the 40‐plus victims.
Narrator: In Southie, two rival gangs share control.
The Killeens own the waterfront.
Brothers Donnie and Kenny run the crew by old‐school rules.
♪♪
They're the definition of organized crime.
Cullen: The Killeens were the sort of
established organized crew.
They had waited their turn, taken their time,
and become the biggest organized ‐crime group in South Boston.
They ran the booking operations, betting on horses, dog races.
Cullen: If you walk into any bar in Southie,
there was a bookie from the Killeen organization
at the end of the bar.
You placed a bet with him.
It was very lucrative.
♪♪
Scumbag!
♪♪
The Killeens were tough guys. They were loan sharks.
But they followed the rules of the streets.
They'd only come after you if there was a reason.
But you'd better hope you never gave them a reason
because they'd hunt you down.
Put you in the ground, if that's what it came to.
Narrator: The Killeens may do things by the book,
but their biggest rivals are an upstart crew
that respects no code.
The Mullens are disorganized crime.
A wild street gang run by
the streetwise brawler Paulie McGonagle.
Cullen: The Mullens didn't respect seniority and authority.
They didn't care.
Their attitude was, "It's our world."
Fight you with their fists or a tire iron
or something like that.
Narrator: Patrick Nee was a leader of the Mullens crew
in the 1970s.
Nee: The Killeens were organized crime.
We just stole.
We weren't interested in any of that because it was like a job.
It was like a 9:00‐to‐5:00 job. You had to be there.
That wasn't our style.
We liked to be out at night stealing.
We'd steal pretty good, and then, uh, we'd party.
Cullen: A lot of the Mullens gang had gone to Vietnam.
They were Marines.
They came back, and I remember one of them told me ‐‐
He goes, "Yeah, we just fought the Viet Cong
in the jungles of ‐‐ of Vietnam.
We didn't give a [bleep] about the Killeens."
♪♪
Narrator: By 1969, the Mullens' turf is expanding
right in the center of Killeen territory.
When Kenny Killeen attacks Mickey Dwyer
outside the Transit Café bar,
it's a direct challenge that won't go unanswered.
Cullen: It was inexorable that they were going to clash
because the Mullens didn't respect the Killeens,
and the Killeens eventually were gonna have
to force them to show some respect.
But like a lot of things that involve the Irish, uh,
the war started with ‐‐ with ‐‐ with too much alcohol
and too much testosterone mixed together.
Those son‐of‐a‐[bleep] Killeens
walking through our streets like they own it,
looking down at us like we should be thankful
for the scraps they drop at the table.
We're gonna strap up and make them pay,
and then they're gonna know what it's like
to go against the Mullens.
Now, are you with me?!
[ Men cheer ]
Are you with me?
[ Men cheer ]
Narrator: The Mullens are poised to strike back,
but before they can make their move,
an ambitious new player emerges with a plan to change the odds.
Jimmy Bulger is a low‐level Killeen enforcer
fresh out of Alcatraz.
But he's no typical gangster.
Cullen: Jimmy Bulger used prison
the way other people would use their years in higher education.
It was his university.
He would say, "I was in Alcatraz."
For a gangster, that's like saying, "I went to Stanford.
I went to Harvard."
He read "The Art of War."
He read several of Machiavelli's books, including "The Prince."
He internalized those lessons ‐‐
the idea of how do you get an upper hand on a rival?
How do you split people and get two sides
fighting against each other and you prevail?
Weeks: He was Machiavellian.
He knew how to use people.
He knew people's weaknesses.
And he was a hunter.
He would spend months if he was after you,
day and night.
He was tenacious.
Narrator: Bulger's not waiting for orders
from the Killeen brothers.
He's gonna hit the Mullens before they can hit back,
and he's gunning right for the top.
♪♪
Hey, Paulie!
[ Gunshots ]
♪♪
But he makes a fatal mistake.
Paulie McGonagle had let his brother
Donnie use his car, and they looked alike.
Nee: From a distance, they looked very much alike,
almost like twins.
He wasn't involved in any criminal activities.
He just happened to be at the wrong place at the wrong time.
♪♪
Narrator: And in tight‐knit Southie,
there's no greater crime than killing a civilian.
♪♪
Nee: We were an isolated community from day one
'cause we're a peninsula.
There was no reason to even drive through Southie.
We had a very safe neighborhood,
in spite of all the gangster stuff.
When we were kids, if we were doing something wrong
four blocks from the house, the people over there would say,
"We're gonna call your mother. We know you."
And say, "Oh, damn, we better ‐‐ You know, we better stop it."
Everyone looked out for each other.
Southie, like a lot of ethnic communities, is very close‐knit.
And even the gangsters abide by the code of the streets.
And part of that code is you don't kill innocent people.
Weeks: You try not to hurt innocent people.
They're not in your life.
You know, they're not in the lifestyle.
Narrator: Donnie and Kenny respect the code,
and murdering a civilian is punishable by death.
♪♪
What's gonna happen to me?
Nothing.
We're at war.
Go get yourself a drink.
Narrator: But it's wartime, and the Killeens
are willing to bend the rules.
They let Jimmy Bulger off the hook.
Nee: They actually made fun of it afterwards.
Said, "Well, he wasn't healthy anyhow.
He would have died sooner or later."
That was their attitude.
They could care less they killed the wrong guy.
It meant nothing to them.
Narrator: But it means everything to Paulie McGonagle.
He launches a crusade to avenge the death of his brother
and turn the streets of Southie into a blood bath.
What time's he gonna be here?
All right.
Good job, Tommy.
Cullen: It escalated things dramatically.
But at that point, the Mullens were absolutely hell‐bent
on a retaliation.
[ Siren wails ]
[ Gunshot ]
♪♪
They were riding up and down the streets,
and wherever they saw each other,
they were shooting at each other.
Bodies started stacking up.
I woke up one morning, and there was a body, uh,
in a car parked in front of my house.
[ Machine‐gun fire ]
Narrator: Mullens hunt down Killeens.
[ Gunshots ]
Killeens kill Mullens.
And the man with the biggest target on his back
is the one who fired the first shots ‐‐
Jimmy "Whitey" Bulger.
[ Gunshots, woman screams ]
Nee: I was chasing Whitey.
And I was chasing him through the projects with a rifle,
dropping down, trying to get him in my sights.
It was different times we tried to get each other.
He was on 2nd Street, we were on 3rd once,
and there was a vacant field between us.
We were both looking for an opportunity to pop each other.
Narrator: Dozens of bodies are dropping on both sides,
but Bulger is hard to kill.
[ Gunshot ]
Nee: I was pulling in one night,
and, uh, Whitey pulled up alongside of me with two ‐‐
There was three of them shooting.
The guy with me called ‐‐ He says, "Duck!"
And he had already rolled out the door.
He caught the play.
And it was too late for me.
I turned, and I went like this.
And I seen all the flashes. And I knew I was getting hit.
I didn't know what I was getting hit with was mostly glass.
♪♪
That's, I think, part of a shotgun pellet.
I leave it there as a reminder.
Narrator: Paulie McGonagle wants this war,
but months into the fight,
his crew is losing.
The Mullens are no match for the Killeens' superior firepower.
But they have a plan to bring down the Killeens for good.
♪♪
And when he hears Donnie Killeen
is having a birthday party for his son,
it's the perfect opportunity to catch him with his guard down.
So his men head out with one order ‐‐
kill Donnie Killeen.
♪♪
What the [bleep] do you want?
♪♪
[ Dog barking ]
♪♪
Cullen: Donnie's funeral ‐‐ the ‐‐ the funeral home
got a bunch of bouquets of flowers.
One of them was actually sent by the Mullens ‐‐
a bouquet that said, "Au revoir."
And, uh, to rub in the indignity,
they sent it cash on delivery.
Anastasia: In this kind of situation,
if you want to come out on top,
you can't be afraid to take risks,
and you got to be tough.
By killing Donnie Killeen,
Paulie McGonagle proved that.
Narrator: The murder of Donnie Killeen
is an act of revenge.
But there's more at stake in this war
than settling a personal vendetta.
The Killeens control the Southie rackets ‐‐
loan‐sharking, bookmaking, and gambling.
With Donnie out of the picture, the Killeens are vulnerable.
Now there's only one man standing between
Paulie McGonagle
and the chance to own Southie.
♪♪
[ Tires screech ]
Kenny narrowly escapes, but the attempt on his life,
just days after the murder of his brother,
is too close a call.
He leaves the gangster game for good.
He survives physically but not mentally.
It took him a long, long time to come out of the house again.
Weeks: Kenny Killeen, who actually started the whole war,
biting the other fella's nose off ‐‐
Uh, you never heard from him again.
He lived in South Boston,
but he basically wouldn't come out of his house.
Anastasia: In a war, you got to be willing
to put your life on the line.
Kenny wasn't willing to do that.
So McGonagle, who had killed one brother
and chased the other brother away, has taken over.
The Mullens have won the war,
even though they're the smallest faction.
Nee: When the gang war started,
the bookies were giving the Mullen gang six months,
and they'd be all dead and be gone.
A year and a half later,
they're giving the Killeens 30 days, maybe.
A complete flip.
Narrator: In a hail of bullets, the underdog Mullens
take control of the Killeens' territory
to become a legitimate crime outfit.
♪♪
Now anyone remaining loyal to the Killeens is a target,
no one more so than Jimmy "Whitey" Bulger.
With the Mullens in power,
Whitey is a dead man walking.
Carr: After the gang war,
Jimmy realizes he needs an intervention
from someone to save his life.
Narrator: While the Mullens have taken control of South Boston,
other Irish crews are still scattered
across the rest of the city,
and the strongest crew of them all is Winter Hill.
Anastasia: The Winter Hill Gang controls Charlestown.
They survived their own mob war back in the '60s.
They're highly organized and consolidate power.
And they're probably the biggest Irish gang
in Boston at the time.
Narrator: Winter Hill is run by gangster royalty ‐‐
Howie Winter.
Nee: Extremely smart, very, very tough, fearless.
Howie didn't know how to be afraid of anything.
But an honorable guy, a decent guy.
We had the utmost respect.
Howie Winter knew everybody in the underworld.
He was very well‐respected by everybody.
He had a lot of gambling operations 30 miles north.
They did stuff on the South Shore of Boston.
And they were much more, uh, expansionist.
He seemed like one of the more old‐school guys.
♪♪
Narrator: Winter Hill is the only gang powerful enough
to keep the Mullens in check.
But with Winter's business booming,
he's not looking to go to war.
Whitey Bulger sets in motion a bold plan.
♪♪
Dangerous time for you to be out on the streets, huh?
♪♪
I spent three years in Alcatraz.
That's dangerous.
So, what brings you here today, Jimmy?
This war in Southie ‐‐ It's hurting everyone.
So if you even threaten to get involved in the fight,
they'd have to make a truce.
Well, I can see how that would help you.
There's something in it for you, too.
A tax.
Every crew's got to kick up a couple coins
to stop an all‐out war.
It's almost free money, Howie.
Yeah, well, that's not a bad idea.
Bulger's plan is for Winter to enforce a truce
and collect a one‐time tax for his trouble.
But Winter's got his own ideas ‐‐
to turn the Southie war to his advantage.
So even though the Mullens have already won,
Howie Winter demands they meet to negotiate a truce.
♪♪
Nee: Howie told us there was no treachery allowed, no weapons,
no riding around the block trying to, you know...
The same thing was told to Whitey.
And Jimmy and Johnny said the same thing.
There would be no shooting at our place.
They were, uh, kind of on their way to being eliminated
until, uh, Bulger had reached out to me
and wanted to see if I could sit down and, uh ‐‐
with the Irish kids who I was very friendly with
and, um, broker a peace deal for them.
So I stepped in and, uh, spoke with them.
Narrator: But this isn't a peace conference.
It's a takeover.
Now I'm gonna tell you how this is gonna play out.
The war between you two is over.
Your two crews are gonna merge,
and they're both gonna be under me.
Now, obviously, there's gonna have to be a guy in charge,
and that guy is Jimmy.
Now, I understand not everybody's gonna like that,
and that's fine. You don't have to like it.
You just have to live with it.
Narrator: Winter places Bulger in charge
because he's proved himself
a fearless enforcer in a vicious gang war
and because he's got the brains to think outside the box.
Cullen: Howie was very impressed with Jimmy,
saw him as a leader ‐‐
somebody who would make money for him.
The Bulger I knew was charming, you know,
and he was, uh, pretty articulate.
You know, when he wanted to charm you
and you just met him and you didn't know anything about him,
he was very charming.
Anastasia: This is an example of how intelligent Howie Winter was.
He listens to Bulger's plan,
and then he tweaks it and makes it work for him.
He doubles the size of his organization
and gets all the rackets and the financial wherewithal
that comes with that.
This is an underworld corporate merger.
Narrator: Bulger's gamble pays off.
This low‐level enforcer on the losing side of a war emerges
as the second‐most‐powerful gangster in South Boston.
But his rise to power doesn't make him bulletproof.
And Paulie McGonagle isn't the kind of guy
that accepts second place.
They killed my [bleep] brother.
So, what are you gonna do?
McGonagle's gonna handle the situation
the only way he knows how ‐‐ kill Jimmy Bulger.
♪♪
The next time they meet,
McGonagle shows up with a Mullen hit man...
♪♪
...and a plot to take his new boss out of the game.
But Whitey is one step ahead.
Jim never forgot what Paulie had done
during the gang wars and stuff.
He was, uh, an enemy of Paulie's.
So one night, Paulie got in the car with him,
and he got killed.
Anastasia: McGonagle may be the toughest guy in Southie,
but he wasn't the smartest.
Narrator: Paulie McGonagle is blind‐sided
because Jimmy saw what he was planning from a mile away.
He goes behind McGonagle's back
and convinces a violent Mullen hit man
to betray Paulie.
Clean it up.
Tommy King, a wild card with a reputation for violence.
Nee: Whitey had seen a weakness in our group
between Paulie McGonagle and Tommy King.
So he worked on Tommy King.
Whitey had convinced Tom that, uh,
Paulie was his mortal enemy
and they had to get rid of him.
And Tommy being the most volatile of the two,
he didn't really think things through.
He was one of us. He was a Mullen ‐‐
extremely, extremely tough, but no control.
Carr: He got arrested one time in the ‐‐ in the '60s.
In jail, he was screaming and yelling.
Finally, the ‐‐ the police chief comes in and says, "Shut up!"
He said, "Or I'm gonna send my toughest guy in,
and he's gonna beat the crap out of you."
And, uh, Tommy King says, "You send him in,
and if I can beat him, your toughest guy,
will you let me go?"
And the captain ‐‐ "Yeah, sure."
He sends in the guy,
and Tommy King beats the crap out of him.
Beats the crap out of him.
They let him go.
That's the kind of guy he was.
♪♪
Narrator: But killing McGonagle violates the truce,
and Howie Winter is a far more dangerous threat
than the Mullens.
Whitey needs to cover his tracks.
Cullen: In that world, when you killed somebody,
you left him on the street.
It was like leaving a calling card.
♪♪
In this case, they disappeared Paulie.
♪♪
Jimmy's brother‐in‐law was actually taken
as a prisoner of war during the Korean War,
and his body was never recovered.
And it was a terrible trauma to Jimmy's sister
and to the whole family.
And to think that 20‐odd years later,
beginning with Paul McGonagle,
Jimmy would just start disappearing bodies
and leaving those families to the same uncertainty and ‐‐
and grief ‐‐ It just struck me as particularly perverse
that somebody who had experienced it in his own family
would then inflict it upon others.
But, you know, that was ‐‐ maybe that was it.
He knew how much it hurt. So that's why he did it.
♪♪
Narrator: Only one loose end remains
to tie Jimmy Bulger to the crime ‐‐
his accomplice, Tommy King.
But Bulger has a scheme for that, too.
Cullen: Jimmy puts it out on the street to the other Mullens guys
that Tommy King killed Paul McGonagle.
This was part of Bulger's operation is there is ‐‐
his MO was to create these divisions ‐‐
the idea of dividing and conquering.
He brought it to his dealings with the Mullens
because obviously, he was concerned that some ‐‐
one of them would eventually figure out
or even just guess and kill him.
Nee: That's when we found out what evil treachery was
'cause once we made peace,
he started manipulating and man‐‐
and maneuvering us.
He was ‐‐ He was a master at putting people in little boxes
where they really couldn't compare notes.
For a long time, we didn't see what he was doing.
Stripping us of our friendships.
It just creeped up on you, and all of a sudden, you feel,
"I'm out here all alone, too."
Anastasia: In a very short period of time,
Bulger has co‐opted a Mullen hit man,
killed his biggest rival,
and now he's taken over the Mullen and Killeen crews.
You got to be impressed with what Bulger has done so far.
Narrator: For the first time in the history
of the Boston underworld,
the Irish mob is a unified force ‐‐
power that's consolidated under a single boss ‐‐
Howie Winter.
♪♪
And Bulger is second in command,
a heartbeat from the top.
[ Telephone ringing ]
‐Yeah. ‐That's what I like to hear.
But Bulger's meteoric rise suddenly comes to a halt.
After six years on the run from the law,
Winters' old number two returns to Boston.
Steve Flemmi is Boston's most notorious hit man.
♪♪
Weeks: Steve Flemmi got the nickname "The Rifleman"
when he was over in Korea.
And when he came back after the war,
he continued to shoot people.
And his choice weapon was an M‐1 Garand.
That's how he kept the nickname "The Rifleman."
He was a funny guy. He was a nice guy.
Just a regular person
who happened to be a homicidal maniac.
Nee: You'd be sitting there talking,
and then he'd be gone.
His eyes would go blank.
We'd all be talking, and he'd just be sitting there
not looking at anything, looking internally,
I guess, whatever was going on in his head.
♪♪
Hey, how you doing? It's gonna be a night.
It's good to be home, boys. How you doing?
When did you get out? You all right?
Anastasia: Flemmi has to flee Boston
because he bombs a lawyer's car,
a prominent attorney.
Blows off his leg.
So he takes off for Montreal.
Good to see you. You guys look good.
Six years later, the FBI closes the case,
and Flemmi can come back to Boston.
Thanks, Howie.
I got something else for you.
Come here, honey.
Here, say ‐‐ say hello to Stephen.
You know I wasn't in jail, right?
Yeah, worse. You were in Canada.
How are you?
Bulger's moving up the ladder.
He's got Howie Winters' ear.
He's a top lieutenant.
Here comes Flemmi back.
Flemmi used to be in that same position.
Now he's in Bulger's way.
Flemmi's a hardened criminal, maybe a psychopath, a murderer.
Narrator: Flemmi's sudden return shakes up Whitey Bulger's world.
But Winter won't tolerate fighting in his ranks.
Ricky saw a couple of patrol cars.
We don't want any contact ‐‐ none at all.
You wanted to see me?
Eddie Connors.
No problem.
Narrator: Winter contracts a hit on a low‐level thug
and orders Flemmi and Bulger to work the job together.
♪♪
The boss is testing his two most hardened killers
to find out who he can trust to make it out alive.
♪♪
[ Guns cock ]
♪♪
Flemmi: It's done.
Winter: Witnesses?
Of course not.
Good work.
♪♪
All good?
Narrator: Howie Winters' strategy
makes the rivals uneasy partners.
And over time, every kill, every vicious shakedown,
every back‐alley beating turns Bulger and Flemmi
into the most feared enforcement team in Boston.
Cullen: One of the first things they did together
is they were brought there rounding up independent bookies
and forcing them to pay rent to the Winter Hill gang.
They would torture these guys ‐‐
threaten people with axes, throw acid on them.
And they thought that was cool.
That was sort of fun.
They seemed to think alike.
They'd really come across as honorable people, you know?
"We'll back you to the hilt. We'll be your best friend.
Don't worry. We've got you covered."
And they were undermining you all the time.
They were always thinking if they have to kill you,
what's the best way to do it?
Where are you at your weakest?
Winter: Flemmi and Bulger ‐‐
You know, they were like two peas in a pod,
you know what I mean?
Uh, they did almost everything together, you know?
So I would say that over the course of time,
they were, uh, pretty tight with each other.
Anastasia: The Bulger‐Flemmi relationship is interesting.
Each brings a different skill set to the underworld.
Flemmi is this ruthless killer, has a reputation for violence.
Bulger is the strategist.
He knows how to figure things out ‐‐ very savvy.
And I think each one of them realizes,
"This guy can help me."
Combined, they prove to be very successful.
Narrator: With Bulger and Flemmi keeping order on the streets
and Howie Winter managing the business,
the Winter Hill gang is raking in the cash.
Man: And I got three more...
And soon enough,
Winter's approached by a local bookie
with a new money‐making scheme.
That's him?
Tony Ciulla.
He calls himself "The Race Fixer."
♪♪
Carr: "Fat" Tony Ciulla.
He was a degenerate gambler and just a real sleazy guy.
First of all, the head of the Mafia tells him,
"Stay ‐‐ Stay away from Fat Tony.
We almost had to kill him once 'cause he was ‐‐ he cheated us."
But Fat Tony goes to him and he says,
"I can fix these horse races. We can make tons of money."
And they ‐‐ they were just overcome with greed.
So even though they had been warned by the Mafia,
for their own good, to stay away from this guy,
they started fixing horse races in all these places.
♪♪
And there was money to be made ‐‐
a lot of money to be made beating up
and threatening jockeys to throw races
so they could bet heavily and make money off that.
Narrator: And there's not just money to be made in Boston.
Soon Winter's race‐fixing scheme is operating across the country,
bringing in upwards of $200,000 a day,
tens of millions of dollars every year.
On top of that, Winter's still got rackets
running 24 hours a day back home.
I heard about that. I was doing the score yesterday.
‐Yeah. ‐That's what I like to hear.
The numbers game ‐‐
an underworld version of the lottery ‐‐
gambling operations, prostitution rings,
even pinball machines.
From just a number of small‐time warring street gangs,
Howie Winter builds one of the biggest criminal organizations
in the country.
♪♪
Doherty: When you combine Howie Winter,
who clearly had a group from the '60s on,
and then you bring in Flemmi and you bring in Bulger,
you have a very formidable group.
And I would say that, at that point in time,
the Mafia was probably more concerned with them
than any other group in the city.
Narrator: While Winter's success makes him rich,
it breaks one of the oldest rules
in the Irish Boston underworld ‐‐
get too big, you'll end up on the radar of the Italian Mafia.
Anastasia: The Italians in the North End
find themselves hemmed in.
Charlestown above, Southie below.
And now, for the first time in history,
that Irish underworld's controlled by one individual.
That creates the threat.
Now you've got a situation where this could lead to war.
Cullen: The Irish and the Italians
always had this fractious relationship
when it came to organized crime.
Jimmy Bulger grew up very suspicious of Italian gangsters.
Narrator: Like everyone who grows up in Southie,
Bulger is taught from an early age Irish gangs
and the Italian mob don't mix.
So when tensions start to rise,
he welcomes the chance for a fight.
But there's a long history of people
who've lost their lives going up against the Italian Mafia.
Nee: Howie always used to tell us, "Be respectful.
Remember your place in the scheme of things."
We were powerful in the sense that ‐‐ here.
They're powerful around the whole country.
We had a lot of crazy tough guys,
but that's a war you can't win.
Anastasia: Howie Winter's a survivor.
That's how he got to be where he was.
He realizes you can make more money
making peace than you can making war.
Narrator: Bulger pushes Winter to go to war with the Italians,
and Winter shuts him down.
But Bulger doesn't give up.
War brings problems. You lose men.
You lose money. You attract law enforcement.
Howie Winter, at this point, is making more money than God.
He doesn't need the aggravation of a war
with the guys from the North End.
Leave it alone, Jimmy.
‐Look, I'm gonna go down ‐‐ ‐I said leave it alone.
Narrator: With Bulger's ruthless ambition,
how long is he gonna let Winter keep him on a leash?
Tell him Howie Winter's here.
♪♪
And Howie Winter can't afford to have the Italians as his enemy.
I appreciate your seeing me, especially on such short notice.
If Winter wants to survive,
he needs the Mafia to see his empire as an asset.
He offers the Italians
a cut of his lucrative race‐fixing scheme.
It's a small price to pay to avoid all‐out war.
This solidifies his status, creates peace.
He's not gonna have a problem from the North End,
and the money's gonna keep rolling in.
It was a business decision.
Doherty: Both groups realized that they could work things out
as opposed to creating a‐a war situation
where one group's trying to take out the other group.
And, you know, that's happened over the years,
but, um, I think they realized
they could operate independently,
but in tandem,
to the success of both organizations.
Narrator: Winter keeps the peace in Boston.
But Bulger sees the new partnership as a serious threat.
Getting into bed with the Italian Mafia
will put the Winter Hill gang under the scrutiny
of the most feared law‐enforcement agency
in the country ‐‐ the FBI.
♪♪
Wyshak: Hoover, who had been the Director of the FBI
since its inception,
had refused to acknowledge the existence of the Mafia.
During the '50s and '60s,
uh, there were a series of Senate hearings.
A, um, individual named Joe Valachi
was really the first made member of organized crime,
uh, to have to testify publicly
about the existence of the Mafia.
And finally, Hoover relented,
acknowledged the existence of the Mafia,
and made it the nation's number‐one priority.
Narrator: Bulger's not gonna let Winter put him
in the cross hairs of the FBI.
♪♪
And just as Bulger's looking for a way to protect himself,
a new player comes home to Boston,
a former Southie kid himself,
but he's not part of the underworld ‐‐
Special Agent John Connolly of the FBI.
♪♪
Cullen: John always looked around at these other FBI agents
and said he thought he was a lot sharper than them.
And he was in a lot of ways.
He was certainly, you know, s‐‐ more streetwise in Boston.
This is where John Connolly grew up.
This put him at an advantage
when he's trying to roll informants.
He was more relatable.
John had, you know, great talent like that
and really could talk a dog, uh, off a bone.
He was good like that.
Narrator: Connolly returns to Boston
with orders to break up the Italian mob.
Carr: They're gonna take down the Mafia
like they took down the Communist party.
And so as long as you're not in the Mafia,
the FBI is willing to cut a deal with you.
Cullen: I think by any objective reading,
to say that the Mafia had ‐‐ was more of a threat
to public safety would ignore the history
of Boston organized crime.
You know, in New York [bleep] obviously, the Mafia is
by far the biggest organized‐crime group
with tentacles into legitimate businesses.
Here in Boston, it wasn't as clear‐cut as that.
The Irish guys were more dangerous.
They killed more people.
The FBI viewed it as that the Mafia was part of a national,
international organization of la Cosa Nostra.
And so by its nature, they were more valuable.
Narrator: But if Connolly wants dirt on the Mafia,
he needs to recruit high‐level informants
from inside the underworld.
And he has someone in mind for the job.
Karas: John Connolly grew up in the projects,
knew Jimmy Bulger when he was growing up.
He was a kid. Jimmy was older.
Jimmy had rescued him once from a fight.
He respected him, thought he was amazing
the way he kind of intervened in the fight.
Cullen: That was something that frankly came to Jimmy by chance,
and it was luck.
It was his luck
that a kid he had stuck up for in the project years ago
had become the FBI agent in charge of,
you know, rounding up informants in the organized‐crime world.
That had nothing to do with Jim Bulger.
That was just ‐‐ Bulger was the beneficiary of that.
[ Siren wailing ]
Narrator: For Bulger, Connolly's the answer to all his problems.
He can protect himself from the FBI
and help them take down the Italians at the same time.
It's Connolly.
Yeah, the parking lot.
See you there.
♪♪
What the hell did you do? Parachute in?
♪♪
"You help us, we'll help you."
I mean, it was very simple.
It was a quid pro quo, you know?
Jim Bulger would, uh, help them ‐‐
help the, uh, FBI against the Mafia,
and in return, the FBI would keep him out of prison.
Here's the deal.
You can keep your money because I'm no goddamn informant.
I'll be your liaison for Winter Hill.
I can work with that.
I'll consult with you on the Italians.
That's it.
They're the enemy.
Fine.
And in return,
full government protection.
You have my word.
Good.
♪♪
Anastasia: This changes the way the game is played here.
Now Bulger's got the FBI in his corner.
He can commit almost any crime he wants,
and he's not gonna suffer any repercussions,
on top of which,
he can use the FBI to go after the Italians,
which is what he always wanted to do.
Cullen: That was right before his eyes ‐‐
the lessons he had learned.
He could visualize it.
"I will give the FBI whatever I choose to give them,
and yet they will take out my competition."
It's a win‐win.
♪♪
Narrator: But the deal only works
if Bulger can keep a secret.
If he's ever found out,
he'll pay a deadly price.
♪♪
[ Sirens wailing ]
But Bulger's got a more immediate problem.
He's promised the feds information
on the Italian Mafia,
and Bulger doesn't have it.
But he just happens to be getting close
to one man who does ‐‐
Steve Flemmi.
Carr: Stevie Flemmi ‐‐ pure Italian,
but he's from Roxbury, which at the time was Irish.
Cullen: If you're an Italian kid back then in Boston,
you aspire to be in the Mafia.
It's sort of like your top choice of college.
Steve Flemmi didn't think like that.
The Mafia desperately wanted him
because they knew how cold and ruthless he was.
They trusted him.
They didn't trust, you know, Jim Bulger.
Jim Bulger was Irish.
Steve Flemmi was the liaison
between Winter Hill and the Mafia.
So he was around them people and everything.
Carr: Jimmy realized that, uh, Stevie was quite an asset
because Stevie could feed information
about the Mafia to Jimmy,
who could then feed it to his FBI agent,
and Jimmy would then become indispensable.
Narrator: But in order to convince Flemmi
to give him information on the Italians,
Bulger has to take the biggest risk of his life.
Even though word getting out means certain death,
he's gonna confess he's working with the FBI.
Triple O's?
Let's go somewhere and talk.
♪♪
It's more of a partnership.
They're not gonna get anything on us or anybody in Southie.
I'm gonna help them take down the Italians.
And I'm supposed to accept
you're not gonna give anything up on us?
Stevie, I'm telling you this because I trust you,
and you can trust me, too.
The feds don't want to deal with us.
They want the Italians.
But Flemmi's response is the last thing Bulger expects.
I know all about the FBI.
Wyshak: From the early '60s to the mid '60s,
there were about 60 gangland murders.
♪♪
And the FBI used the ongoing gang war to generate informants
by essentially helping some of these members
survive the gang war.
One of those individuals at the time was Stevie Flemmi.
Because the leadership of organized crime
is well‐insulated,
we're employing an approach
that includes long‐term investigations
and the use of such sensitive techniques
as selected informants.
Cullen: FBI agents back then took active roles
and set people up to be murdered.
They were kingmakers.
So Flemmi's sitting there and realizing how much the FBI
is not just this sort of passive onlooker
as the gangsters kill each other,
but are actually active players.
So when the FBI approaches Flemmi and say,
"We want you to work for us,"
Flemmi had seen it with his own eyes that,
"I'd be out of my mind not to get involved in this.
As long as I'm working for them, they're not gonna set me up."
And so by the time Flemmi hooks up with Jim Bulger,
he has 10 years of this under his belt.
Narrator: Bulger's revelation is the opportunity
that Flemmi's been waiting for.
But before he'll cooperate,
Flemmi wants to know if he can trust John Connolly.
So Bulger sets up a meeting.
Connolly: How you doing, Steve?
♪♪
How long you known Jimmy?
Long enough.
Jim Connolly gives Flemmi the same offer he gave Bulger ‐‐
dig up dirt on the Italian mob,
and the FBI will protect him.
Anastasia: Flemmi was an FBI informant
before he fled to Montreal.
He knows the upside. He knows the downside.
So I think he's willing to make this deal
'cause he wants to get back into that situation.
♪♪
How'd it go?
Same as you.
Let's get out of here.
Carr: They had that in common ‐‐ a little secret
that they, uh, couldn't share with anybody else.
So that made them closer.
Nee: If one of them started talking
about what the other one was doing,
the whole thing would have come unraveled.
They couldn't afford to give anyone
any hint what they were doing
because we would have landed on them real hard.
We would have killed them.
♪♪
Narrator: Bulger has made himself bulletproof.
It's security that comes just in the nick of time
because the Winter Hill gang is about to take a massive hit...
♪♪
...when one of its two main sources of income,
the home‐spun illegal lottery game known as "the numbers,"
is put out of business
by the Massachusetts State Lottery.
♪♪
Cullen: People in working‐class neighborhoods in Boston,
across all ethnic lines,
played the numbers such that the number
that the wise guys used ‐‐
it was printed in the Record American.
When I was a kid, my mother used to send me out to get the Record
when it came out at 9:00.
And I had to trudge down there sometime in the snow
so she could see if she hit the number.
And then the Massachusetts State Lottery is established.
Carr: First, it was just Saturday,
then it was Saturday and Wednesday night.
Then it became a daily number.
Then they had Powerball.
Then they had Keno. Then they had punchcards.
There was just no way that the numbers racket,
which is just in a few inner‐city neighborhoods,
could ever compete.
♪♪
Anastasia: For years, Howie Winter was making all kind of money,
rising, controlling.
He's a major gangster in ‐‐ in Boston,
but now there's a downturn.
Narrator: Winter's problems go from bad to worse when Tony Ciulla,
the man in charge of Winter's race‐fixing empire,
is arrested in New Jersey.
Foley: He had information ‐‐
A lot of the stuff that was going on
with the Winter Hill Gang ‐‐
the drug distribution, the money that they were making out there,
the ‐‐ the racing,
there was, you know, stolen property,
and he was familiar with what was going on.
He could hurt them if he, you know, wanted to just come in
and testify, you know, or ‐‐ or become a witness.
Narrator: The one‐two punch is a disaster for Winter's bottom line,
and what's worse, he should have seen it coming.
♪♪
Ciulla brought this deal to him, and it was a big moneymaker,
but from the beginning, the guys on the North End
were telling him, "Ciulla can't be trusted.
Be careful."
Winter either didn't listen or was blinded
by the money that was coming in.
And now he found himself in a situation
where he was gonna pay the ultimate price.
Narrator: Tony Ciulla vows not to talk to the feds.
But for a fee of $10,000,
he tells his story to the press.
The master race‐fixer explains every detail of the operation,
and though he doesn't name names,
the article reveals that there's an ongoing FBI probe
into the masterminds of the ring up in Boston.
Howie Winter's been the most powerful Irish gangster
in the country for the last four years.
Winter's empire is dangling by a thread,
and it's not just Winter in danger.
If Ciulla talks, Bulger and Flemmi
will be brought down, too.
Carr: The big thing for Stevie and Jimmy
was were they gonna be indicted, too?
That was their question.
They ‐‐ They were in the middle of this race‐fixing scheme.
They were doing ‐‐ They were handing the layoff bets
for the, uh ‐‐ for the fixed races.
And so they were as deep into it as everybody else.
Narrator: If indictments are handed out,
Bulger and Flemmi will be trapped in a no‐win scenario.
Either they go down with Winter,
or they get the FBI to protect them,
revealing their status as informants
to the entire underworld.
Either way, they're finished.
Narrator: Under pressure to pay his debts,
Winter digs himself a deeper hole
when he seeks a loan from another crew.
But this isn't just any gang.
Howie needed to borrow money from the Boston Mafia ‐‐
Jerry Angiulo.
And that's when he got in hock to the Mafia.
I got a line on something that can't miss.
Bookie up in Providence wants to give me
eight points on the dollar.
But I want to give you guys a chance to get in.
Bottom line ‐‐ $200,000 large.
And I guarantee it.
Narrator: Winter asks the Italian Mafia
for a $200,000 loan.
It's a stunning turn of events when you think about it.
The Italians are looking at Winter.
Two, three years ago, he's a rival.
They're worried about him taking over everything.
Now he comes hat‐in‐hand and he becomes a customer.
Narrator: With the loan secured, Winter squeezes as much money
as he can out of his last remaining moneymaker ‐‐
pinball machines.
In the early 1970s,
pinball machines are illegal in the bars of Boston.
Back when Winter was riding high,
he pays off local officials to change the laws
and make pinball legal.
[ Pinball machine chiming ]
He paid off the right people at City Hall,
and then everybody said, "Oh, it's open season for pinball.
We can sell our pinball machines."
God knows there's where the ‐‐ the money is.
They're all making, like ‐‐
on one machine, they'd make like $5,000 a week.
And they had machines in every ‐‐ every Elks Club,
every ‐‐ every club around.
Narrator: But now that Winter's hungry for cash,
he wants every penny from the pinball machines for himself.
Winter started going around to them and saying,
"Hey, pal, I'm the one that made the capital expenditure here.
I bribed everybody.
It ain't in writing, but you better stay out."
They were just, again, so greedy that they went to people
who went to the cops.
Narrator: Howie Winter's desperation makes him reckless.
When bar owners begin to report the dealings to the cops,
it gives law enforcement a window
to finally take down the biggest Irish gangster in the city.
The man leading the charge
is an ambitious assistant district attorney,
John Kerry.
Carr: The first assistant district attorney
is John Forbes Kerry.
He has that lean and hungry look, as they say.
He figures he's gonna make his bones by taking out the ‐‐
the top gangster in, uh ‐‐ in Middlesex County.
Howie Winter was a big gangster.
He's well‐known in the community.
He's been involved in all these gang wars.
He's walked away.
People get dead if they cross him.
It's a big deal to bring down a gangster like that.
Anastasia: Kerry's kind of a new breed of the DA ‐‐
out to make a name for himself,
building cases that he knows are high‐profile.
All of that is bad for Howie Winter.
Narrator: Howie Winter is arrested for extortion
late in 1978.
♪♪
He's convicted and sentenced to 20 years.
Howie Winter took over the Winter Hill gang in 1966.
12 years later, he's transformed the small street crew
into a citywide syndicate that runs the Boston rackets.
But his conviction leaves a vacancy
at the top of the Irish Mob hierarchy.
And two ruthless killers want to be the ones to fill it.
♪♪
But before Flemmi or Bulger can make a move,
Winter Hill is floored by another bombshell.
♪♪
Tony Ciulla starts to talk.
[ Gavel bangs ]
Judge: Can you list for the court
the other high‐ranking members of the Winter Hill gang?
Ciulla took the stand and said
that I was the mastermind behind it
and that I, uh...
[Clears throat]
enticed jockeys, said that I had spoke with a jockey,
said that I had beat up a jockey,
or I had him beaten up.
Ciulla didn't really get heavy time.
But obviously, he didn't want to do time.
And he got his sentence reduced dramatically by cooperating,
but in doing so, he implicated some of the,
you know, most dangerous, lethal people
in the criminal underworld here in Boston ‐‐
Howie Winter, Whitey Bulger, and Steve Flemmi.
Gave them all up.
Narrator: After nearly a decade scheming his way to the top,
and just when he's poised to seize power,
Bulger is in real trouble.
But his talent for strategy has always set him apart.
As the rest of Winter Hill panics,
Whitey Bulger makes a final gamble
and disappears.
While Flemmi sweats it out back in Boston,
Bulger takes matters into his own hands.
He goes on an all‐expenses‐paid trip
with John Connolly.
You'd actually be shocked, but the lobster's not half bad.
Get whatever you want. I got the check.
Ho.
Connolly's the only man in Boston with the power
to remove Bulger from the indictments.
And Whitey Bulger is luring him deeper into his trap.
Weeks: This was all part of
Jimmy treating Connolly to a vacation.
I think it was the blizzard of '78 they went down there.
Jim Bulger had corrupted John Connolly.
Narrator: And the vacation is just the start of it.
Cullen: Bulger might have acted like he was all palsy‐walsy,
but he was always looking for a weakness,
and the weakness they found was a guy that had champagne tastes
but was being paid with beer money.
Narrator: Vacations, bribes, cash payouts ‐‐
Bulger flips his relationship with the FBI.
Carr: Connolly ‐‐ He was the quintessential bad cop.
This was in the days before direct deposit,
and, uh, one of the FBI secretaries,
uh, went into his desk looking for something,
and she found 10 un‐cashed checks.
That's how much cash he had.
He didn't even need to cash his checks.
He ‐‐ He was flush.
He had a house in a nice Boston suburb.
He buys a big place down on the Cape, uh,
in one of the nicest spots on the Cape.
Weeks: One time, uh, John Connolly went out and bought a boat.
40‐foot, double‐beam, 12‐foot‐wide boat or whatever.
And Jim Bulger made him get rid of it
'cause he was attracting too much attention to himself.
How could he afford this based on an FBI salary?
Anastasia: Uh, the relationship between Bulger and Connolly
has been turned upside‐down.
Bulger's provided Connolly with thousands of dollars.
In essence, he's put an FBI agent on his payroll.
Connolly, conversely, has to keep Bulger happy,
or Connolly ends up going down with Bulger.
Narrator: Now Connolly works for Bulger.
It got to the point, obviously, where now,
in order for Connolly to survive,
he had to keep Bulger and Flemmi out of harm's way.
[ Telephone rings ]
Doherty: When you work your whole life on one side of the ‐‐
the track, and then you cross over,
it's probably the biggest disappointment
in law enforcement to see that happen.
Yeah, get me John Morris. Thanks.
Narrator: If Connolly wants to protect himself,
he needs to keep Bulger and Flemmi off the list.
But to do it, he needs his supervisor's approval.
Carr: John Morris is this FBI agent who's not from Boston
and he's brought in and he's just a career guy,
and he's a very weak person.
Narrator: Going against protocol,
Morris agrees to meet with Bulger and Flemmi
at his own home.
Cullen: His wife was like, "Screw this.
I'm not cooking for a bunch of criminals."
So Morris, I think, made the steaks, and they sat around.
But I remember Stevie saying that what him and Jimmy Bulger
noticed most about Morris that night
is how many glasses of wine he drank.
And that's ‐‐ They were always looking for weaknesses.
They're like, "How can ‐‐ What can we exploit with this guy?"
From that moment on, um, their nickname for Morris was "Vino,"
and one of the, um, tactics they used in terms
of ingratiating themselves to Morris
was to send him cases of wine 'cause they were looking ‐‐
"What can we use on this guy?
How can we get our hooks into him?"
And they did.
Narrator: And Bulger and Flemmi don't stop with cases of wine.
They pay for trips, send Morris cash and clothing,
jewelry ‐‐ anything he asks for.
Cullen: That's why John Connolly and his supervisor,
John Morris, went directly to the head
of the Justice Department's Organized Crime Strike Force
and said, "You got to take these guys out of the indictment.
We need them to stay on the street
'cause they're working for us."
If you look at what Bulger's accomplished at this point,
i‐it's really, from an underworld perspective, amazing.
I mean, he won a gang war that he actually lost,
gotten away with murder, eliminated rivals.
He's got the FBI on his payroll.
And now his influence is such that he can keep
his name off a federal indictment.
Narrator: Now that Bulger has secured his position,
there's only one man standing between him
and complete control of Winter Hill ‐‐
the same guy who helped him get to where he is ‐‐
Steve Flemmi.
Wait a minute.
Something wrong?
We've been working together now almost five years, Stevie.
[ Sighs ]
Long time.
And we can rule Boston together, too.
♪♪
But there can only be one boss.
It's all laid out in front of Flemmi.
From day one, Bulger's been scheming for this exact moment.
At the first meeting with Connolly,
he could see the possibilities.
And in return, full government protection.
Then Bulger brings Flemmi into the deal
to make his own position stronger.
How'd it go?
Same as you.
And finally, Bulger corrupted John Connolly without Flemmi.
Get whatever you want. I got the check.
You just said we were in this together.
Five years.
It would be a shame to throw it all away like that.
♪♪
Anastasia: Bulger gave Connolly the money.
Bulger took Connolly to Mexico.
Bulger took information from Flemmi
and gave it to Connolly as his own.
So at this point, it's Bulger who's got access to Connolly,
and not Flemmi.
Mother [bleep]
Cullen: It showed that in the end,
if you had to say who was smarter,
it was Jimmy.
The indictment comes out.
Everybody in the Winter Hill are named,
and only Bulger and Flemmi
are named as un‐indicted co‐conspirators.
They're in the conspiracy, but they're not indicted.
I didn't believe it. I didn't know ‐‐
want to believe it that Bulger and Flemmi
were un‐indicted co‐conspirators.
Weeks: Actually, uh, some people said it was the first time
they heard the term "un‐indicted co‐conspirators."
Everybody else was indicted,
and they were left off the indictment.
Narrator: Over the course of a decade,
Bulger has killed and schemed his way to the top.
And done it all while concealing his treachery
from fellow gang members.
♪♪
When Jimmy and Stevie were still on the street, again,
I think if I was the Winter ‐‐ other Winter Hill guys,
I would have said, "These guys are rats.
What the hell are they doing on the street, and I'm locked up?"
But that isn't their ‐‐ They looked at it,
"At least we have these guys out there,
and they can look after our business."
Nee: He planned it all along. We didn't know that.
He was making a‐all these moves for where to look to be
in a position where he knew everything.
♪♪
To Jimmy.
Together: To Jimmy!
♪♪
To Southie!
[ Men cheering ]
To Southie!
♪♪
Cullen: Jimmy Bulger had no conscience.
He was totally depraved, totally self‐centered,
blindly ambitious, extremely greedy,
and that's what made him what he was.
He ‐‐ He was willing to stop at nothing to succeed.
♪♪
Narrator: The Boston Irish Mob has a new kingpin.
♪♪
Anastasia: In the 1980s, Bulger, in essence,
takes over the Boston underworld.
His gang is in total control.
Nobody's gonna challenge him.
And he's got the FBI in his pocket.
So no other law‐enforcement agency is able to build a case.
He's the man. It's his city.
Doherty: A lot of times, they'd just extort people for money.
If you were operating or did anything anywhere
in the South Boston area,
they'd grab people, they'd ‐‐
they'd put them in a location where they'd be secluded,
all alone, vulnerable, and then they'd tell them,
"You have one of two ways to go,
and, you know, one is out the door in a body bag,
and the opposite way is you pay."
♪♪
Carr: They developed almost an assembly line
for killing people.
Jimmy would handle the actual execution.
Kevin Weeks would strip the body,
and he and sometimes Pat Nee would dig the hole.
Stevie's role was to, uh, pull the teeth.
So he had a pair of pliers,
and it was hard to get the pliers into the mouth
to pull the teeth out.
Jimmy's girlfriend was a dental hygienist.
One day he said, "Can you bring home the catalog?"
He orders a pair of, uh, state‐ of‐the‐art tooth extractors.
Christmas rolls around.
Jimmy says, "Merry Christmas, Stevie."
Cullen: As those years go on, I mean, Bulger and Flemmi
knew there'd be a day of reckoning.
Narrator: And the same thing that brought Jimmy Bulger
to power is what brings him down ‐‐
turning rat.
Cullen: They go on making their money and all through the early '90s,
but then the biggest thing that changed in this whole equation
is that a group of state police officers
and DEA agents determined to work around the FBI
and build a case against Bulger and Flemmi.
And they did, slowly but surely,
flipping bookmakers who had been extorted
and had been threatened with violence,
uh, by Bulger and Flemmi.
Narrator: The case becomes insurmountable.
But Whitey Bulger slips away
before the authorities can grab him,
thanks to one last tip from John Connolly.
It starts the longest manhunt in US history.
16 years on the lam.
12 of them spent on the FBI's 10 Most Wanted List.
The authorities give up hope of ever finding him alive.
They catch him in Santa Monica, California.
Reporter: After spending 16 years on the run,
the FBI has caught Boston mob boss James "Whitey" Bulger.
Reporter #2: Boston crime boss James "Whitey" Bulger
has been arrested.
Reporter #3: Now Bulger is facing charges
in connection with 19 murders.
Today marks the moment of when James "Whitey" Bulger
will finally face justice for his crimes.
Carr: He was a very successful criminal.
Although, ultimately, now he's, uh, what, 87 years old.
And he's going to die in prison.
♪♪