How to Become a Mob Boss (2023) s01e05 Episode Script

Play the Long Game

[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.
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 Gang,
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 killer.
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.
[Dick] 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 killer.
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.
[Dick] 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 Gang.
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 murder.
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.
[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.
[Dick] Stevie Flemmi
and Johnny Martorano grew up in Boston.
Both have killed 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]
[narrator] Tommy King is a longshoreman
and an enforcer in the Winter Hill Gang.
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.
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 murder himself
and left town to hide.
[Dick] 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 killed.
And that's what kept his gang 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 murder 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 guns 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 murder.
[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.
[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 murder 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.
[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.
[Dick] 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?
[Dick] 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 Gang,
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 gunman
and was summarily murdered
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.
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 killed women.
They killed 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.
[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 illegal 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 guns
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.
[Dick] 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]
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