01x05 - Play the Long Game

[bunniefuu]

[narrator] As we've seen,

becoming a successful mob boss

requires discipline,

an entrepreneurial mindset,

and the willingness

to do anything to protect your power.

Put these qualities to work,

and you can reap truly handsome rewards.

However, the often inevitable fall

from criminal glory can be steep.

Most mob bosses end up dead or in jail.

[screaming]

It's just the way it is.

There is no Florida community

of retired bosses.

[narrator] But you can chart

a more comfortable future

by taking care of every detail

and always thinking two steps ahead.

Nobody embodied

these lessons more expertly

than the master of manipulation

who became Boston's most powerful

and feared mob boss,

James "Whitey" Bulger.

He could be very charming

when he wanted something from you,

and then, like a snake,

he could turn around

and bite you the next second.

[man] It all comes back to Whitey.

His survival, his power, his control,

and if he feels any of that is at risk,

then anything goes.

[narrator] By predicting

and obliterating every threat,

Whitey dominated

Beantown's criminal underworld

for nearly two decades.

And when the walls started closing in,

he performed the ultimate vanishing act.

[reporter] For the last 16 years,

the notorious Boston mob boss was a ghost.

[narrator] Let Whitey show you

how to go the distance

by never getting caught unprepared.

[theme music playing]

During Whitey Bulger's bloody reign

as the head of Boston's Winter Hill g*ng,

he was suspected of ordering

at least 19 murders

while raking in an estimated

30 million in illicit cash.

Bulger, by far,

has to be the most notorious

and I'd argue most successful

criminal from Boston.

[man] It was all, I think,

a big chess game to him.

Creating a criminal organization

that was really successful,

and he was outwitting

everyone along the way.

[narrator] To understand how Whitey

charted his course to mob boss infamy

and eventually

became America's Most Wanted man,

you first need to know

a few things about this crafty k*ller.

Whitey Bulger, he grew up

in poverty in South Boston.

He was the oldest of three boys.

And there were three girls in the family.

He wasn't really into school.

He wasn't really into church.

He was into kind of being wild

and causing trouble.

Billy Bulger was one

of Whitey's younger siblings.

Unlike Whitey, Billy excelled in school,

and he went on to have

a very successful career in politics.

[d*ck] Bill Bulger was feared

in the state house.

If you crossed him,

there would be a price to pay.

Obviously, Whitey is

a gangster and a k*ller.

He had a whole different toolbox

to work with.

Bulger had really good luck

at committing crime

and getting away with it

from a very young age.

He got arrested a bunch of times,

but only one of the charges even stuck.

[d*ck] In the 1950s, two of the men

who he had robbed banks with

ratted him out.

So he felt deeply betrayed,

but he also understood the value

of providing information

and being an informant.

[narrator] After rising through the ranks,

Whitey made it to the top of New England's

most feared Irish-American syndicate,

the Winter Hill g*ng.

He achieved an enormous

amount of power and wealth,

but he wasn't real showy about that.

One of the things that led

to Bulger's success for so many years

is that he preferred the shadows.

He was more of a name that people

had heard, but never really seen.

So, even veteran investigators

had never actually seen him.

[narrator] It was all part of Whitey's

carefully crafted strategy

to get away with m*rder.

So, how do you make sure

you stay in the game for the long haul?

Follow along with the playbook

and find out.

If you want to endure as a mob boss,

you need to maintain

total control of your operation

and you can't tolerate any weak links.

Unless you have very tight control

over the people that are running things

for you on the street,

anything could happen.

Attention!

[narrator] And when it came

to sniffing out

potential problems in his ranks,

Whitey Bulger was a master.

He had a very powerful organization,

but he ran it

like a closely-held corporation.

Bulger's group answered

to no one but themselves.

It wasn't like a Mafia organization

where you have capos,

lieutenants and all that kind of thing.

There were very few people

in his inner circle.

His idea was this deadly power center.

[narrator] For most of Whitey's run,

that center included just two key allies.

Steve Flemmi and Johnny Martorano.

[d*ck] Stevie Flemmi

and Johnny Martorano grew up in Boston.

Both have k*lled multiple times.

He could trust those guys.

And in that sense,

they had the right stuff, the résumé

to be aligned with Whitey Bulger.

[narrator] As for everyone else,

to avoid Whitey's wrath,

they had to follow very specific rules.

It was understood that there would be

no flamboyant displays of wealth.

Don't antagonize law enforcement

for unnecessary reasons.

You don't talk your criminal business

in front of others.

And above all, don't rat anyone out.

Any deviation from that

is when Whitey would go ballistic.

[yelling incoherently]

[inaudible]

[narrator] Tommy King is a longshoreman

and an enforcer in the Winter Hill g*ng.

He was a tough, sweet guy,

Tommy, and he was one of us,

but he had a drinking problem.

[narrator] Whitey and Tommy

never quite hit it off.

[gangster] Both of you go to hell!

[narrator] And Whitey sees

Tommy's increasingly erratic behavior

as a threat.

[grunts]

So one day, Whitey invites Tommy

to come along as backup on a hunting trip

to take out a rival gangster.

Steve Flemmi

and John Martorano join in as well.

As they head out of town,

Tommy shows off his new bulletproof vest

and jokes that if they don't find

their target, they can try it out.

Whitey has a different plan.

The hit was a success,

but Whitey knows he'll likely be suspected

in Tommy's disappearance.

So he spreads the story of suggesting

Tommy committed a m*rder himself

and left town to hide.

[d*ck] Whitey gets behind

a propaganda machine.

He's good at this too. Selling a story.

[narrator] Whether his people

believe it or not,

they know better

than to ask too many questions.

Bulger had little patience for people

he viewed as a liability to him,

and he didn't hesitate

to have them k*lled.

And that's what kept his g*ng in line.

No need to get tough.

They were afraid of him.

[narrator] Running a tight ship will keep

your long-term plan in good health.

But when m*rder is your medicine,

you need to watch out for side effects.

How do you make sure

your rising body count

doesn't trip you up?

Let's be honest.

All mob bosses need

to cut loose threads from time to time.

But if you don't want to end your days

behind bars, every detail counts.

Any crime you commit,

you wanna get rid of evidence,

so you don't go to jail.

It's as simple as that.

[narrator] And that often means

going the extra mile.

You burn the clothes,

throw the g*ns right in the ocean.

Get rid of everything.

There should be no car.

There should be no DNA.

If there's no body, there's no m*rder.

[narrator] Little wonder

why all the best bosses

know the value of a good cover-up.

When Pablo Escobar wanted to get rid

of a pair of disloyal underlings

he thought were cheating him,

he allegedly invited them

to his private prison

and had them incinerated.

When former Gambino boss,

Paul Castellano,

needed a rival disappeared,

he relied on hitman Roy DeMeo

and his Gemini method,

named after DeMeo's favorite hangout.

It involved fully draining

a corpse of blood

to minimize mess

before cutting it into tiny pieces.

While Salvatore Riina eliminated

his problems using a practice

known as lupara bianca,

which could involve

dissolving victims in acid,

feeding them to hogs,

or even throwing them

into a steel smelter.

But none of these masters

covered their tracks as painstakingly

as Whitey Bulger.

[Emily] A lot of gangland slayings,

bodies would be

just left in trunks of cars.

Or sometimes just left on the street.

Bulger and his crew

went out of their way to hide bodies.

Really far out of their way

to make sure the bodies were buried

where nobody would ever find them.

In case the body was discovered,

he'd cut fingers off, pull out their teeth

because someone's identity could be

revealed through their dental records.

So that was the technique,

if you had the stomach for it.

[narrator] But when you're trying

to win the long game,

you need to make sure

that proof of your handiwork

stays hidden permanently.

Goodbye, Dr. Farb.

You may have been a crummy dentist,

but you were a nice fella.

[roaring]

[narrator] Whitey has a few go-to spots

that he returns to

to conduct his business.

[Brian] One of the locations

was right in South Boston

on one of the main streets.

It was an older home

that had a dirt basement.

[thunder crashes]

[man] No!

[narrator] It soon earns a nickname,

the Haunty

[man screams]

where after his bloody work is complete,

Whitey makes good use

of the home's unfinished basement.

But one day, there's a problem.

The Haunty goes up for sale.

Whitey has a troubling vision

of the future.

[woman screams]

[narrator] He needs to move.

So, Whitey picks an appropriate night

for his ghoulish plan

and brings along an associate to help.

[man coughs]

They load the bodies into a station wagon

and drive them across town

to a field beside a fireman's union hall.

Ever the planner, Whitey already had

new resting places prepared.

Ensuring that neither Whitey

nor the Haunty's new owners

end up with an unpleasant surprise.

Happy Halloween.

He was a cunning strategist.

He was a very clever

and very dangerous guy.

And that's why many of his murders were,

in fact, left unsolved for many years.

[narrator] A solid body disposal program

will help

keep m*rder detectives off your trail,

but there's an even better way

to stay ahead of every potential problem.

All it takes is the right hookup.

As a mob boss, you can use creative means

to keep cops out of your business.

But to achieve real staying power,

you should pursue a deeper relationship.

If you want a long shelf life,

find a way to get someone

on the inside of law enforcement,

as high up as you can, to watch your back.

That is huge.

And that is so much of what made

Whitey Bulger the mob boss that he was.

Bulger had a lot of local contacts

in the state police, Boston police,

and he would pay off

law enforcement officials,

especially around Christmas.

[laughs]

[narrator] But Whitey wanted

the ultimate inside track,

and he knew just how to get it

through an old friend.

John Connolly grew up

in South Boston, and he idolized Whitey.

[Brian] Connolly was younger

than Whitey Bulger.

Bulger protected him from some fistfight

years ago, and as a result,

Connolly always felt

some sort of, uh, loyalty to Bulger.

[narrator] And Whitey had a plan

to collect on that debt.

Throughout 1974, Whitey begins

meeting covertly with Connolly

to discuss rekindling the relationship.

Connolly's convinced

that getting an in with the gangster

would transform his career,

while Whitey has his own agenda,

VIP treatment from the local FBI.

He begins feeding Connolly tips

on his rivals

inside the Boston underworld,

so federal agents

can do his dirty work for him.

Whitey is credited with helping the feds

nab their most coveted prize,

the head of Boston's Italian Mafia,

Jerry Angiulo

[camera shutters clicking]

by securing inside information

about Angiulo's headquarters,

which they used to set up wiretaps.

It leads to a successful takedown

of the entire Angiulo crime family.

[siren wailing]

With the Mafia sidelined,

Whitey becomes even more powerful.

Connolly also keeps

Whitey's name off of official FBI reports

and tips him off about investigations.

It's a profitable relationship all around.

And as the line between

criminal and cop begins to blur,

Whitey himself becomes nearly untouchable.

[d*ck] I don't think

in the history of American crime

there's anyone who achieved

what Whitey Bulger achieved

when it came to having

corrupt law enforcement

feeding you valuable intel.

[siren wailing]

[Emily] So many people

in law enforcement were going crazy

trying to get Bulger on something.

Everybody wondered, "How does he know?

It seems like he knows what we're doing."

Sometimes that's 'cause he did.

[narrator] But while sharing secrets

with the feds can preserve your freedom,

it's not going to win

many friends among your peers.

No one likes a rat.

How do you keep

your dirty secret from coming out?

[d*ck] Whitey had a reputation

as the ultimate stand-up guy.

Someone who doesn't talk

to the authorities.

Doesn't give anybody up.

Doesn't give any information,

no matter what the circumstances,

no matter what the threat,

no matter what the pressure.

You stand up and say nothing.

[narrator] Of course,

Whitey's actual relationship

with law enforcement was more complicated.

Whitey always had to be on his guard,

always, 'cause he was

living a double life.

The underworld had no idea he was a rat.

So, he was always living with that.

He knew what would happen if we found out.

[narrator] Need more proof?

See what happened

to these other chatty dons.

Big Jack Zelig,

boss of Manhattan's Eastman g*ng,

got knocked off in 1912

while riding the Second Avenue trolley

after his people learned

he was in the pocket

of a corrupt NYPD lieutenant.

Chicago crime boss James Ragen

was ambushed and shot after exposing

the top echelon

of the Chicago mob to the feds.

While recovering in the hospital,

he identified the g*nman

and was summarily m*rder*d

via mercury poisoning.

And Bonanno family captain,

Dominick Napolitano,

got whacked for allowing

FBI agent Joseph Pistone,

aka Donnie Brasco,

to infiltrate the family.

He was ultimately found

with his hands cut off,

a traditional penalty

for divulging Mafia secrets.

When it came to protecting

Whitey Bulger's stand-up image,

his homicidal reputation came in handy.

No one suspected someone

as dangerous as him

to be a top FBI informant,

basically ratting on other people

to enhance his position,

increase his power.

There had been rumors,

but most people scoffed at the rumors

because it was too ridiculous.

[narrator] To keep it that way,

nothing and no one was off-limits.

Debra Davis is the longtime mistress

of Steve Flemmi, Whitey's right-hand man.

Generally,

Whitey doesn't pay her much mind

until she catches wind of Whitey's secret

that he's been working

with the FBI for years.

Flemmi, who has developed

his own FBI connection,

tells Whitey everything's under control.

Whitey isn't convinced.

And when Flemmi and Debra's relationship

starts to hit the rocks,

the risk becomes untenable.

Whitey has Flemmi set a trap,

telling Debra he wants to show her

a house he wants to buy for her.

But when Flemmi gives her a tour,

she ends up

with a different sort of closing.

[woman screaming]

[narrator] Cleanup is quick

and thorough.

They bury Debra

next to Tommy King on Tenean Beach.

And just like that,

Whitey's secret stays hidden.

This guy had no empathy

for anybody, only for himself.

He didn't care for no one, this guy.

They k*lled women.

They k*lled innocent people.

It was amazing,

the things he was capable of doing

in the name of his security

and his freedom.

[narrator] But even if you take

all the right precautions

and have all the right protection,

no one stays untouchable forever.

When the tide turns, you need to be ready.

Let the playbook show you the way.

[Brian] When a mob boss

wants to evade justice,

many of them

have to eventually go on the run.

But that's difficult to do

if you're not disciplined.

[narrator] But as we've seen

Need a little grass?

[narrator] discipline was

Whitey's middle name.

No, thanks.

[man] Whitey was always

in full control of his environment.

I've never seen him drink.

He never socialized.

He didn't mix with people.

That's a vulnerability

if you're doing the wrong thing.

[Brian] He was often thinking about,

"Well, what if I do get charged?"

"I should be prepared."

Whitey had been planning for years

for the curtain to fall on his show.

He had a well-planned escape route

where he could completely

drop off the face of the Earth.

[narrator] The Whitey Bulger method

for getting out of Dodge

consists of a few key steps

that any outlaw can follow.

Step one, start saving early.

Stash cash, jewelry, and fake passports

in safe deposit boxes all over the globe.

Step two, build aliases.

Pay top dollar

for fake IDs, birth certificates,

and credit cards in various names,

then use new identities

to open bank accounts.

Step three, find the perfect hiding place.

Choose somewhere you can easily blend in,

some place with turnover and tourism.

Outsiders will be less likely

to take note of your quirks.

Once you've found your new hometown,

it's onto the next step.

[shushing]

[narrator] Tell no one when,

where, or how you're leaving.

You'd be surprised

how many people forget this one.

Finally, it's time to make your getaway.

But when you do,

don't forget the most important rule

of all for going underground,

be ready for anything.

[narrator] For 20 years,

Whitey's guardian angel and the FBI

had kept him safe from prosecution.

But by the early 1990s,

Whitey's luck was starting to run out.

[camera shutters clicking]

In the early 1990s, we began

an investigation of Bulger and his group.

Ultimately, we had enough evidence

to charge him with racketeering,

along with several other individuals.

The FBI, of course,

knew we were seeking the indictment.

[narrator] Whitey's top ally,

Steve Flemmi, is quickly arrested.

It is a state trooper and a DEA agent

who captured Flemmi.

And then the others went over

to South Boston trying to find Whitey,

but it was to no avail.

He was long gone.

[narrator] Now, how do you think

that happened?

Bulger was tipped off by Connolly,

and he was able to take off

before the indictment came down.

[Brian] It was enormously frustrating

to work on a case

which the main target

disappears into the mist.

So, the strong message is

that law enforcement

will continue the effort until we get him.

[newscaster] And while

his whereabouts are a mystery,

Whitey Bulger's victims

have been turning up all over Boston.

[man] My thoughts were,

they're not gonna find him.

I know how he prepares.

[narrator] It's one thing

to make a clean getaway.

Staying safe for the long haul

will take genius-level execution.

So, follow the master.

When you've made a name for yourself

as one of history's top mob bosses,

authorities won't be so quick

to let you just disappear.

So much about being a mob boss

is being somebody.

You have to be at ease

and make a transition

to being unrecognized and unacknowledged,

to being a nobody.

[reporter] Whitey Bulger,

a known master of disguise,

has not been seen in six years.

The trail is cold, even though

there's a one million dollar reward out

for information leading to his arrest.

[Brian] Even members

of law enforcement in Boston

couldn't tell you what he looked like.

In fact, he probably looked like

half the people at Fenway Park.

[narrator] But even if people

don't know your face,

keeping yourself off the radar

will be a full-time job.

Whitey excelled

at this second career as well.

After crossing the country,

Whitey and his longtime girlfriend,

Catherine Greig, settle in Santa Monica,

where they take the names

Charlie and Carol Gasko.

Just a harmless retiree

and his loving wife,

living in a rent-stabilized

apartment building near the Pacific Ocean.

They were your typical snowbirds

from the East Coast,

living in a warm climate,

and, you know,

not causing any problems for anyone.

[narrator] Tenants in their building

are friendly,

but the Gaskos choose

to keep their distance,

especially Charlie.

However, there are some people

he makes a point of seeking out.

[Brian] Bulger would befriend

homeless people

or people really in desperate situations,

and he would pay them for their ID.

For Bulger, it was like gold.

[narrator] Whitey would tell them

he's an ill*gal immigrant from Canada

in need of medical help

and offer to pay hundreds of dollars

for their driver's license

and social security number.

Most agree.

To avoid being tracked,

Whitey and Catherine rotate identities

at dental and medical appointments.

And when they cross into Tijuana

to buy Whitey's heart medication,

authorities pay no mind.

Everybody just sees

Charlie and Carol Gasko

enjoying their golden years

by the California coast.

The perfect cover for the perfect couple.

For 16 sun-soaked years, Charlie

I mean, Whitey, lived his best life

as authorities continued their efforts

to track him down.

[Emily] The greatest escape

in mob history.

It has to be up there, right?

[narrator] But despite

Whitey's extraordinary efforts,

the dream didn't last forever.

We begin this morning

with a bombshell arrest overnight

[reporter 1] After spending 16 years

on the run,

the FBI has caught Boston mob boss

[reporter 2] James "Whitey" Bulger

is captured

in a Santa Monica apartment house,

ending a worldwide manhunt

that spanned 16 years.

[Brian] Ultimately, Bulger was captured

in large part

because of a cat, of all things.

There was a woman

who was watching TV in Iceland,

and she spent her winters in Santa Monica.

And she had bonded

with another woman over a cat.

They were both cat lovers.

This was Catherine Greig.

The two of them were friends.

And when she saw

Bulger and Greig on TV years later,

she immediately reported this to the FBI.

[reporter 3] Within 24 hours,

authorities lured Bulger outside

and arrested him.

And confiscated nearly 30 g*ns

and hundreds of thousands of dollars

stashed in the apartment.

[man] We have captured one of the FBI's

ten most wanted fugitives.

A man notorious in Boston

and around the world.

[narrator] Whitey's meticulous planning

kept him alive and out of jail

until the ripe old age of 81,

making him one of mob bossery's

true iron men.

[d*ck] He chose a profession,

the underworld life of crime,

where the shelf life

isn't particularly long.

But he managed to survive for decades.

[narrator] But as impressive

a feat as that was,

achieving the ultimate promise

of becoming a mob boss

requires grander ambitions.

For the playbook's final chapter,

I'll show you how to harness

your criminal skills into wealth,

power, and influence

beyond your wildest dreams.

Your guide

who else but the king

of cocaine himself, Pablo Escobar.

[theme music playing]