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[narrator] As we've seen,
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becoming a successful mob boss
requires discipline,
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an entrepreneurial mindset,
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and the willingness
to do anything to protect your power.
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Put these qualities to work,
and you can reap truly handsome rewards.
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However, the often inevitable fall
from criminal glory can be steep.
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Most mob bosses end up dead or in jail.
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[screaming]
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It's just the way it is.
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There is no Florida community
of retired bosses.
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[narrator] But you can chart
a more comfortable future
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by taking care of every detail
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and always thinking two steps ahead.
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Nobody embodied
these lessons more expertly
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than the master of manipulation
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who became Boston's most powerful
and feared mob boss,
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James " Whitey" Bulger.
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He could be very charming
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when he wanted something from you,
and then, like a snake,
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he could turn around
and bite you the next second.
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[man] It all comes back to Whitey.
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His survival, his power, his control,
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and if he feels any of that is at risk,
then anything goes.
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[narrator] By predicting
and obliterating every threat,
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Whitey dominated
Beantown's criminal underworld
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for nearly two decades.
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And when the walls started closing in,
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he performed the ultimate vanishing act.
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[reporter] For the last 16 years,
the notorious Boston mob boss was a ghost.
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[narrator] Let Whitey show you
how to go the distance
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by never getting caught unprepared.
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[theme music playing]
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During Whitey Bulger's bloody reign
as the head of Boston's Winter Hill Gang,
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he was suspected of ordering
at least 19 murders
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while raking in an estimated
30 million in illicit cash.
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Bulger, by far,
has to be the most notorious
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and I'd argue most successful
criminal from Boston.
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[man] It was all, I think,
a big chess game to him.
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Creating a criminal organization
that was really successful,
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and he was outwitting
everyone along the way.
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[narrator] To understand how Whitey
charted his course to mob boss infamy
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and eventually
became America's Most Wanted man,
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you first need to know
a few things about this crafty killer.
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Whitey Bulger, he grew up
in poverty in South Boston.
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He was the oldest of three boys.
And there were three girls in the family.
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He wasn't really into school.
He wasn't really into church.
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He was into kind of being wild
and causing trouble.
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Billy Bulger was one
of Whitey's younger siblings.
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Unlike Whitey, Billy excelled in school,
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and he went on to have
a very successful career in politics.
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[Dick] Bill Bulger was feared
in the state house.
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If you crossed him,
there would be a price to pay.
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Obviously, Whitey is
a gangster and a killer.
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He had a whole different toolbox
to work with.
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Bulger had really good luck
at committing crime
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and getting away with it
from a very young age.
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He got arrested a bunch of times,
but only one of the charges even stuck.
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[Dick] In the 1950s, two of the men
who he had robbed banks with
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ratted him out.
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So he felt deeply betrayed,
but he also understood the value
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of providing information
and being an informant.
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[narrator] After rising through the ranks,
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Whitey made it to the top of New England's
most feared Irish-American syndicate,
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the Winter Hill Gang.
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He achieved an enormous
amount of power and wealth,
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but he wasn't real showy about that.
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One of the things that led
to Bulger's success for so many years
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is that he preferred the shadows.
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He was more of a name that people
had heard, but never really seen.
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So, even veteran investigators
had never actually seen him.
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[narrator] It was all part of Whitey's
carefully crafted strategy
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to get away with murder.
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So, how do you make sure
you stay in the game for the long haul?
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Follow along with the playbook
and find out.
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If you want to endure as a mob boss,
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you need to maintain
total control of your operation
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and you can't tolerate any weak links.
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Unless you have very tight control
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over the people that are running things
for you on the street,
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anything could happen.
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Attention!
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[narrator] And when it came
to sniffing out
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potential problems in his ranks,
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Whitey Bulger was a master.
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He had a very powerful organization,
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but he ran it
like a closely-held corporation.
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Bulger's group answered
to no one but themselves.
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It wasn't like a Mafia organization
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where you have capos,
lieutenants and all that kind of thing.
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There were very few people
in his inner circle.
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His idea was this deadly power center.
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[narrator] For most of Whitey's run,
that center included just two key allies.
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Steve Flemmi and Johnny Martorano.
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[Dick] Stevie Flemmi
and Johnny Martorano grew up in Boston.
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Both have killed multiple times.
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He could trust those guys.
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And in that sense,
they had the right stuff, the résumé
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to be aligned with Whitey Bulger.
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[narrator] As for everyone else,
to avoid Whitey's wrath,
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they had to follow very specific rules.
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It was understood that there would be
no flamboyant displays of wealth.
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Don't antagonize law enforcement
for unnecessary reasons.
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You don't talk your criminal business
in front of others.
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And above all, don't rat anyone out.
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Any deviation from that
is when Whitey would go ballistic.
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[yelling incoherently]
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[inaudible]
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[narrator] Tommy King is a longshoreman
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and an enforcer in the Winter Hill Gang.
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He was a tough, sweet guy,
Tommy, and he was one of us,
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but he had a drinking problem.
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[narrator] Whitey and Tommy
never quite hit it off.
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[gangster] Both of you go to hell!
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[narrator] And Whitey sees
Tommy's increasingly erratic behavior
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as a threat.
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[grunts]
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So one day, Whitey invites Tommy
to come along as backup on a hunting trip
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to take out a rival gangster.
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Steve Flemmi
and John Martorano join in as well.
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As they head out of town,
Tommy shows off his new bulletproof vest
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and jokes that if they don't find
their target, they can try it out.
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Whitey has a different plan.
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The hit was a success,
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but Whitey knows he'll likely be suspected
in Tommy's disappearance.
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So he spreads the story of suggesting
Tommy committed a murder himself
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and left town to hide.
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[Dick] Whitey gets behind
a propaganda machine.
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He's good at this too. Selling a story.
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[narrator] Whether his people
believe it or not,
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they know better
than to ask too many questions.
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Bulger had little patience for people
he viewed as a liability to him,
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and he didn't hesitate
to have them killed.
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And that's what kept his gang in line.
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No need to get tough.
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They were afraid of him.
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[narrator] Running a tight ship will keep
your long-term plan in good health.
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But when murder is your medicine,
you need to watch out for side effects.
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How do you make sure
your rising body count
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doesn't trip you up?
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Let's be honest.
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All mob bosses need
to cut loose threads from time to time.
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But if you don't want to end your days
behind bars, every detail counts.
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Any crime you commit,
you wanna get rid of evidence,
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so you don't go to jail.
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It's as simple as that.
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[narrator] And that often means
going the extra mile.
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You burn the clothes,
throw the guns right in the ocean.
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Get rid of everything.
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There should be no car.
There should be no DNA.
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If there's no body, there's no murder.
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[narrator] Little wonder
why all the best bosses
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know the value of a good cover-up.
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When Pablo Escobar wanted to get rid
of a pair of disloyal underlings
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he thought were cheating him,
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he allegedly invited them
to his private prison
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and had them incinerated.
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When former Gambino boss,
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Paul Castellano,
needed a rival disappeared,
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he relied on hitman Roy DeMeo
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and his Gemini method,
named after DeMeo's favorite hangout.
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It involved fully draining
a corpse of blood
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to minimize mess
before cutting it into tiny pieces.
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While Salvatore Riina eliminated
his problems using a practice
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known as lupara bianca ,
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which could involve
dissolving victims in acid,
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feeding them to hogs,
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or even throwing them
into a steel smelter.
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But none of these masters
covered their tracks as painstakingly
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as Whitey Bulger.
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[Emily] A lot of gangland slayings,
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bodies would be
just left in trunks of cars.
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Or sometimes just left on the street.
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Bulger and his crew
went out of their way to hide bodies.
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Really far out of their way
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to make sure the bodies were buried
where nobody would ever find them.
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In case the body was discovered,
he'd cut fingers off, pull out their teeth
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because someone's identity could be
revealed through their dental records.
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So that was the technique,
if you had the stomach for it.
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[narrator] But when you're trying
to win the long game,
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you need to make sure
that proof of your handiwork
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stays hidden permanently.
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Goodbye, Dr. Farb.
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You may have been a crummy dentist,
but you were a nice fella.
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[roaring]
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[narrator] Whitey has a few go-to spots
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that he returns to
to conduct his business.
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[Brian] One of the locations
was right in South Boston
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on one of the main streets.
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It was an older home
that had a dirt basement.
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[thunder crashes]
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[man] No!
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[narrator] It soon earns a nickname,
the Haunty...
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[man screams]
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...where after his bloody work is complete,
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Whitey makes good use
of the home's unfinished basement.
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But one day, there's a problem.
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The Haunty goes up for sale.
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Whitey has a troubling vision
of the future.
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[woman screams]
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[narrator] He needs to move.
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So, Whitey picks an appropriate night
for his ghoulish plan...
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and brings along an associate to help.
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[man coughs]
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They load the bodies into a station wagon
and drive them across town
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to a field beside a fireman's union hall.
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Ever the planner, Whitey already had
new resting places prepared.
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Ensuring that neither Whitey
nor the Haunty's new owners
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end up with an unpleasant surprise.
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Happy Halloween.
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He was a cunning strategist.
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He was a very clever
and very dangerous guy.
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And that's why many of his murders were,
in fact, left unsolved for many years.
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[narrator] A solid body disposal program
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will help
keep murder detectives off your trail,
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but there's an even better way
to stay ahead of every potential problem.
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All it takes is the right hookup.
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As a mob boss, you can use creative means
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to keep cops out of your business.
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But to achieve real staying power,
you should pursue a deeper relationship.
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If you want a long shelf life,
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find a way to get someone
on the inside of law enforcement,
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as high up as you can, to watch your back.
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That is huge.
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And that is so much of what made
Whitey Bulger the mob boss that he was.
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Bulger had a lot of local contacts
in the state police, Boston police,
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and he would pay off
law enforcement officials,
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especially around Christmas.
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[laughs]
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[narrator] But Whitey wanted
the ultimate inside track,
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and he knew just how to get it...
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through an old friend.
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John Connolly grew up
in South Boston, and he idolized Whitey.
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[Brian] Connolly was younger
than Whitey Bulger.
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Bulger protected him from some fistfight
years ago, and as a result,
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Connolly always felt
some sort of, uh, loyalty to Bulger.
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[narrator] And Whitey had a plan
to collect on that debt.
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Throughout 1974, Whitey begins
meeting covertly with Connolly
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to discuss rekindling the relationship.
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Connolly's convinced
that getting an in with the gangster
240
00:14:38,879 --> 00:14:43,383
would transform his career,
while Whitey has his own agenda,
241
00:14:43,467 --> 00:14:46,219
VIP treatment from the local FBI.
242
00:14:47,262 --> 00:14:49,180
He begins feeding Connolly tips
243
00:14:49,264 --> 00:14:51,892
on his rivals
inside the Boston underworld,
244
00:14:53,018 --> 00:14:56,396
so federal agents
can do his dirty work for him.
245
00:14:59,733 --> 00:15:04,320
Whitey is credited with helping the feds
nab their most coveted prize,
246
00:15:04,404 --> 00:15:07,824
the head of Boston's Italian Mafia,
Jerry Angiulo...
247
00:15:07,908 --> 00:15:09,117
[camera shutters clicking]
248
00:15:09,201 --> 00:15:12,287
...by securing inside information
about Angiulo's headquarters,
249
00:15:12,371 --> 00:15:14,748
which they used to set up wiretaps.
250
00:15:16,375 --> 00:15:20,670
It leads to a successful takedown
of the entire Angiulo crime family.
251
00:15:20,754 --> 00:15:21,588
[siren wailing]
252
00:15:21,672 --> 00:15:26,301
With the Mafia sidelined,
Whitey becomes even more powerful.
253
00:15:27,386 --> 00:15:31,556
Connolly also keeps
Whitey's name off of official FBI reports
254
00:15:31,640 --> 00:15:33,767
and tips him off about investigations.
255
00:15:35,268 --> 00:15:38,063
It's a profitable relationship all around.
256
00:15:39,564 --> 00:15:42,818
And as the line between
criminal and cop begins to blur,
257
00:15:43,318 --> 00:15:46,863
Whitey himself becomes nearly untouchable.
258
00:15:47,656 --> 00:15:50,533
[Dick] I don't think
in the history of American crime
259
00:15:50,617 --> 00:15:54,162
there's anyone who achieved
what Whitey Bulger achieved
260
00:15:54,246 --> 00:15:56,956
when it came to having
corrupt law enforcement
261
00:15:57,040 --> 00:15:59,042
feeding you valuable intel.
262
00:15:59,126 --> 00:16:00,293
[siren wailing]
263
00:16:00,377 --> 00:16:03,338
[Emily] So many people
in law enforcement were going crazy
264
00:16:03,422 --> 00:16:05,757
trying to get Bulger on something.
265
00:16:07,009 --> 00:16:10,428
Everybody wondered, "How does he know?
It seems like he knows what we're doing."
266
00:16:10,512 --> 00:16:12,431
Sometimes that's 'cause he did.
267
00:16:13,807 --> 00:16:17,644
[narrator] But while sharing secrets
with the feds can preserve your freedom,
268
00:16:17,728 --> 00:16:21,273
it's not going to win
many friends among your peers.
269
00:16:22,024 --> 00:16:23,942
No one likes a rat.
270
00:16:24,818 --> 00:16:27,738
How do you keep
your dirty secret from coming out?
271
00:16:33,618 --> 00:16:37,330
[Dick] Whitey had a reputation
as the ultimate stand-up guy.
272
00:16:37,414 --> 00:16:40,249
Someone who doesn't talk
to the authorities.
273
00:16:40,333 --> 00:16:41,834
Doesn't give anybody up.
274
00:16:41,918 --> 00:16:45,254
Doesn't give any information,
no matter what the circumstances,
275
00:16:45,338 --> 00:16:47,966
no matter what the threat,
no matter what the pressure.
276
00:16:48,050 --> 00:16:50,135
You stand up and say nothing.
277
00:16:50,802 --> 00:16:52,929
[narrator] Of course,
Whitey's actual relationship
278
00:16:53,013 --> 00:16:55,766
with law enforcement was more complicated.
279
00:16:56,808 --> 00:16:58,768
Whitey always had to be on his guard,
280
00:16:58,852 --> 00:17:01,605
always, 'cause he was
living a double life.
281
00:17:03,190 --> 00:17:06,610
The underworld had no idea he was a rat.
282
00:17:07,444 --> 00:17:11,823
So, he was always living with that.
He knew what would happen if we found out.
283
00:17:13,366 --> 00:17:14,659
[narrator] Need more proof?
284
00:17:14,743 --> 00:17:17,245
See what happened
to these other chatty dons.
285
00:17:19,748 --> 00:17:23,418
Big Jack Zelig,
boss of Manhattan's Eastman Gang,
286
00:17:23,502 --> 00:17:25,294
got knocked off in 1912
287
00:17:25,378 --> 00:17:28,715
while riding the Second Avenue trolley
after his people learned
288
00:17:28,799 --> 00:17:31,718
he was in the pocket
of a corrupt NYPD lieutenant.
289
00:17:32,511 --> 00:17:36,347
Chicago crime boss James Ragen
was ambushed and shot after exposing
290
00:17:36,431 --> 00:17:39,184
the top echelon
of the Chicago mob to the feds.
291
00:17:39,810 --> 00:17:43,062
While recovering in the hospital,
he identified the gunman
292
00:17:43,146 --> 00:17:46,108
and was summarily murdered
via mercury poisoning.
293
00:17:46,858 --> 00:17:49,527
And Bonanno family captain,
Dominick Napolitano,
294
00:17:49,611 --> 00:17:53,281
got whacked for allowing
FBI agent Joseph Pistone ,
295
00:17:53,365 --> 00:17:56,868
aka Donnie Brasco,
to infiltrate the family.
296
00:17:57,452 --> 00:17:59,579
He was ultimately found
with his hands cut off,
297
00:17:59,663 --> 00:18:02,999
a traditional penalty
for divulging Mafia secrets.
298
00:18:07,546 --> 00:18:11,382
When it came to protecting
Whitey Bulger's stand-up image,
299
00:18:11,466 --> 00:18:14,177
his homicidal reputation came in handy.
300
00:18:14,261 --> 00:18:15,887
No one suspected someone
301
00:18:15,971 --> 00:18:19,974
as dangerous as him
to be a top FBI informant,
302
00:18:20,058 --> 00:18:21,768
basically ratting on other people
303
00:18:21,852 --> 00:18:24,395
to enhance his position,
increase his power.
304
00:18:24,479 --> 00:18:27,774
There had been rumors,
but most people scoffed at the rumors
305
00:18:27,858 --> 00:18:29,693
because it was too ridiculous.
306
00:18:30,694 --> 00:18:35,157
[narrator] To keep it that way,
nothing and no one was off-limits.
307
00:18:38,660 --> 00:18:43,415
Debra Davis is the longtime mistress
of Steve Flemmi, Whitey's right-hand man.
308
00:18:43,999 --> 00:18:46,585
Generally,
Whitey doesn't pay her much mind
309
00:18:47,502 --> 00:18:50,254
until she catches wind of Whitey's secret
310
00:18:50,338 --> 00:18:53,008
that he's been working
with the FBI for years.
311
00:18:53,633 --> 00:18:57,011
Flemmi, who has developed
his own FBI connection,
312
00:18:57,095 --> 00:19:00,473
tells Whitey everything's under control.
313
00:19:01,099 --> 00:19:02,976
Whitey isn't convinced.
314
00:19:03,560 --> 00:19:07,355
And when Flemmi and Debra's relationship
starts to hit the rocks,
315
00:19:07,439 --> 00:19:09,441
the risk becomes untenable.
316
00:19:12,444 --> 00:19:14,654
Whitey has Flemmi set a trap,
317
00:19:14,738 --> 00:19:18,742
telling Debra he wants to show her
a house he wants to buy for her.
318
00:19:19,784 --> 00:19:21,828
But when Flemmi gives her a tour,
319
00:19:22,454 --> 00:19:25,290
she ends up
with a different sort of closing.
320
00:19:27,834 --> 00:19:31,254
[woman screaming]
321
00:19:31,755 --> 00:19:33,131
[narrator] Cleanup is quick
322
00:19:33,965 --> 00:19:34,883
and thorough.
323
00:19:37,677 --> 00:19:40,639
They bury Debra
next to Tommy King on Tenean Beach.
324
00:19:42,349 --> 00:19:45,852
And just like that,
Whitey's secret stays hidden.
325
00:19:46,853 --> 00:19:50,231
This guy had no empathy
for anybody, only for himself.
326
00:19:50,315 --> 00:19:52,150
He didn't care for no one, this guy.
327
00:19:52,234 --> 00:19:53,568
They killed women.
328
00:19:54,194 --> 00:19:55,820
They killed innocent people.
329
00:19:55,904 --> 00:19:58,239
It was amazing,
the things he was capable of doing
330
00:19:58,323 --> 00:20:02,118
in the name of his security
and his freedom.
331
00:20:02,786 --> 00:20:04,955
[narrator] But even if you take
all the right precautions
332
00:20:05,664 --> 00:20:07,957
and have all the right protection,
333
00:20:08,041 --> 00:20:10,335
no one stays untouchable forever.
334
00:20:10,835 --> 00:20:13,672
When the tide turns, you need to be ready.
335
00:20:14,256 --> 00:20:16,299
Let the playbook show you the way.
336
00:20:21,888 --> 00:20:24,516
[Brian] When a mob boss
wants to evade justice,
337
00:20:25,100 --> 00:20:28,061
many of them
have to eventually go on the run.
338
00:20:30,480 --> 00:20:33,942
But that's difficult to do
if you're not disciplined.
339
00:20:34,734 --> 00:20:35,985
[narrator] But as we've seen...
340
00:20:36,069 --> 00:20:37,069
Need a little grass?
341
00:20:37,153 --> 00:20:39,488
[narrator] ...discipline was
Whitey's middle name.
342
00:20:39,572 --> 00:20:40,448
No, thanks.
343
00:20:41,950 --> 00:20:45,661
[man] Whitey was always
in full control of his environment.
344
00:20:45,745 --> 00:20:47,122
I've never seen him drink.
345
00:20:47,622 --> 00:20:50,333
He never socialized.
He didn't mix with people.
346
00:20:51,001 --> 00:20:53,628
That's a vulnerability
if you're doing the wrong thing.
347
00:20:54,671 --> 00:20:57,548
[Brian] He was often thinking about,
"Well, what if I do get charged?"
348
00:20:57,632 --> 00:20:58,842
"I should be prepared."
349
00:21:01,553 --> 00:21:05,890
Whitey had been planning for years
for the curtain to fall on his show.
350
00:21:06,975 --> 00:21:09,435
He had a well-planned escape route
351
00:21:09,519 --> 00:21:12,647
where he could completely
drop off the face of the Earth.
352
00:21:14,983 --> 00:21:17,443
[narrator] The Whitey Bulger method
for getting out of Dodge
353
00:21:17,527 --> 00:21:20,989
consists of a few key steps
that any outlaw can follow.
354
00:21:21,489 --> 00:21:23,950
Step one, start saving early.
355
00:21:24,784 --> 00:21:29,831
Stash cash, jewelry, and fake passports
in safe deposit boxes all over the globe.
356
00:21:30,582 --> 00:21:33,084
Step two, build aliases.
357
00:21:34,336 --> 00:21:36,921
Pay top dollar
for fake IDs, birth certificates,
358
00:21:37,005 --> 00:21:38,757
and credit cards in various names,
359
00:21:39,591 --> 00:21:42,427
then use new identities
to open bank accounts.
360
00:21:43,595 --> 00:21:46,765
Step three, find the perfect hiding place.
361
00:21:47,432 --> 00:21:50,142
Choose somewhere you can easily blend in,
362
00:21:50,226 --> 00:21:53,063
some place with turnover and tourism.
363
00:21:54,397 --> 00:21:57,817
Outsiders will be less likely
to take note of your quirks.
364
00:21:59,277 --> 00:22:02,697
Once you've found your new hometown,
it's onto the next step.
365
00:22:02,781 --> 00:22:03,614
[shushing]
366
00:22:03,698 --> 00:22:08,411
[narrator] Tell no one when,
where, or how you're leaving.
367
00:22:09,412 --> 00:22:12,415
You'd be surprised
how many people forget this one.
368
00:22:13,333 --> 00:22:15,794
Finally, it's time to make your getaway.
369
00:22:17,045 --> 00:22:18,004
But when you do,
370
00:22:18,088 --> 00:22:21,925
don't forget the most important rule
of all for going underground,
371
00:22:22,425 --> 00:22:24,052
be ready for anything.
372
00:22:27,430 --> 00:22:30,224
[narrator] For 20 years,
Whitey's guardian angel and the FBI
373
00:22:30,308 --> 00:22:32,643
had kept him safe from prosecution.
374
00:22:32,727 --> 00:22:37,273
But by the early 1990s,
Whitey's luck was starting to run out.
375
00:22:37,357 --> 00:22:38,775
[camera shutters clicking]
376
00:22:39,943 --> 00:22:45,698
In the early 1990s, we began
an investigation of Bulger and his group.
377
00:22:46,282 --> 00:22:51,037
Ultimately, we had enough evidence
to charge him with racketeering,
378
00:22:51,121 --> 00:22:52,830
along with several other individuals.
379
00:22:52,914 --> 00:22:55,959
The FBI, of course,
knew we were seeking the indictment.
380
00:22:57,335 --> 00:23:00,505
[narrator] Whitey's top ally,
Steve Flemmi, is quickly arrested.
381
00:23:01,464 --> 00:23:05,927
It is a state trooper and a DEA agent
who captured Flemmi.
382
00:23:06,678 --> 00:23:11,682
And then the others went over
to South Boston trying to find Whitey,
383
00:23:11,766 --> 00:23:13,351
but it was to no avail.
384
00:23:13,435 --> 00:23:14,686
He was long gone.
385
00:23:15,603 --> 00:23:17,939
[narrator] Now, how do you think
that happened?
386
00:23:19,149 --> 00:23:21,025
Bulger was tipped off by Connolly,
387
00:23:22,110 --> 00:23:25,405
and he was able to take off
before the indictment came down.
388
00:23:29,117 --> 00:23:31,869
[Brian] It was enormously frustrating
to work on a case
389
00:23:31,953 --> 00:23:35,122
which the main target
disappears into the mist.
390
00:23:35,206 --> 00:23:36,707
So, the strong message is
391
00:23:36,791 --> 00:23:40,461
that law enforcement
will continue the effort until we get him.
392
00:23:40,545 --> 00:23:43,047
[newscaster] And while
his whereabouts are a mystery,
393
00:23:43,131 --> 00:23:46,509
Whitey Bulger's victims
have been turning up all over Boston.
394
00:23:47,260 --> 00:23:49,470
[man] My thoughts were,
they're not gonna find him.
395
00:23:49,554 --> 00:23:51,139
I know how he prepares.
396
00:23:52,015 --> 00:23:54,392
[narrator] It's one thing
to make a clean getaway.
397
00:23:55,435 --> 00:23:59,647
Staying safe for the long haul
will take genius-level execution.
398
00:24:00,148 --> 00:24:01,691
So, follow the master.
399
00:24:10,033 --> 00:24:14,245
When you've made a name for yourself
as one of history's top mob bosses,
400
00:24:14,329 --> 00:24:17,832
authorities won't be so quick
to let you just disappear.
401
00:24:18,374 --> 00:24:21,043
So much about being a mob boss
is being somebody.
402
00:24:21,127 --> 00:24:23,379
You have to be at ease
403
00:24:23,463 --> 00:24:27,508
and make a transition
to being unrecognized and unacknowledged,
404
00:24:27,592 --> 00:24:28,968
to being a nobody.
405
00:24:29,761 --> 00:24:32,388
[reporter] Whitey Bulger,
a known master of disguise,
406
00:24:32,472 --> 00:24:35,057
has not been seen in six years.
407
00:24:35,141 --> 00:24:39,228
The trail is cold, even though
there's a one million dollar reward out
408
00:24:39,312 --> 00:24:41,731
for information leading to his arrest.
409
00:24:43,191 --> 00:24:45,192
[Brian] Even members
of law enforcement in Boston
410
00:24:45,276 --> 00:24:46,861
couldn't tell you what he looked like.
411
00:24:48,154 --> 00:24:51,741
In fact, he probably looked like
half the people at Fenway Park.
412
00:24:53,618 --> 00:24:55,995
[narrator] But even if people
don't know your face,
413
00:24:56,538 --> 00:24:59,749
keeping yourself off the radar
will be a full-time job.
414
00:25:00,250 --> 00:25:03,586
Whitey excelled
at this second career as well.
415
00:25:06,172 --> 00:25:07,798
After crossing the country,
416
00:25:07,882 --> 00:25:12,553
Whitey and his longtime girlfriend,
Catherine Greig, settle in Santa Monica,
417
00:25:12,637 --> 00:25:15,640
where they take the names
Charlie and Carol Gasko.
418
00:25:16,558 --> 00:25:19,477
Just a harmless retiree
and his loving wife,
419
00:25:19,561 --> 00:25:23,481
living in a rent-stabilized
apartment building near the Pacific Ocean.
420
00:25:24,148 --> 00:25:28,444
They were your typical snowbirds
from the East Coast,
421
00:25:28,528 --> 00:25:30,029
living in a warm climate,
422
00:25:30,113 --> 00:25:33,199
and, you know,
not causing any problems for anyone.
423
00:25:35,243 --> 00:25:37,161
[narrator] Tenants in their building
are friendly,
424
00:25:37,245 --> 00:25:39,872
but the Gaskos choose
to keep their distance,
425
00:25:40,415 --> 00:25:42,166
especially Charlie.
426
00:25:43,626 --> 00:25:48,214
However, there are some people
he makes a point of seeking out.
427
00:25:48,798 --> 00:25:51,967
[Brian] Bulger would befriend
homeless people
428
00:25:52,051 --> 00:25:56,680
or people really in desperate situations,
and he would pay them for their ID.
429
00:25:56,764 --> 00:25:58,474
For Bulger, it was like gold.
430
00:25:58,975 --> 00:26:02,102
[narrator] Whitey would tell them
he's an illegal immigrant from Canada
431
00:26:02,186 --> 00:26:03,605
in need of medical help
432
00:26:04,147 --> 00:26:06,148
and offer to pay hundreds of dollars
433
00:26:06,232 --> 00:26:09,360
for their driver's license
and social security number.
434
00:26:10,612 --> 00:26:11,696
Most agree.
435
00:26:13,615 --> 00:26:15,032
To avoid being tracked,
436
00:26:15,116 --> 00:26:19,162
Whitey and Catherine rotate identities
at dental and medical appointments.
437
00:26:20,121 --> 00:26:24,542
And when they cross into Tijuana
to buy Whitey's heart medication,
438
00:26:25,126 --> 00:26:27,211
authorities pay no mind.
439
00:26:28,713 --> 00:26:31,131
Everybody just sees
Charlie and Carol Gasko
440
00:26:31,215 --> 00:26:34,719
enjoying their golden years
by the California coast.
441
00:26:36,304 --> 00:26:40,016
The perfect cover for the perfect couple.
442
00:26:44,145 --> 00:26:47,731
For 16 sun-soaked years, Charlie...
443
00:26:47,815 --> 00:26:51,402
I mean, Whitey, lived his best life
444
00:26:51,486 --> 00:26:55,114
as authorities continued their efforts
to track him down.
445
00:26:55,198 --> 00:26:57,450
[Emily] The greatest escape
in mob history.
446
00:26:58,368 --> 00:26:59,786
It has to be up there, right?
447
00:27:00,662 --> 00:27:03,747
[narrator] But despite
Whitey's extraordinary efforts,
448
00:27:03,831 --> 00:27:06,000
the dream didn't last forever.
449
00:27:06,084 --> 00:27:08,377
We begin this morning
with a bombshell arrest overnight...
450
00:27:08,461 --> 00:27:10,754
[reporter 1] After spending 16 years
on the run,
451
00:27:10,838 --> 00:27:12,673
the FBI has caught Boston mob boss...
452
00:27:12,757 --> 00:27:14,174
[reporter 2] ...James "Whitey" Bulger
453
00:27:14,258 --> 00:27:16,343
is captured
in a Santa Monica apartment house,
454
00:27:16,427 --> 00:27:19,680
ending a worldwide manhunt
that spanned 16 years.
455
00:27:19,764 --> 00:27:21,599
[Brian] Ultimately, Bulger was captured
456
00:27:21,683 --> 00:27:24,977
in large part
because of a cat, of all things.
457
00:27:28,231 --> 00:27:31,692
There was a woman
who was watching TV in Iceland,
458
00:27:31,776 --> 00:27:34,778
and she spent her winters in Santa Monica.
459
00:27:34,862 --> 00:27:38,449
And she had bonded
with another woman over a cat.
460
00:27:38,533 --> 00:27:41,577
They were both cat lovers.
This was Catherine Greig.
461
00:27:42,495 --> 00:27:44,246
The two of them were friends.
462
00:27:44,330 --> 00:27:48,542
And when she saw
Bulger and Greig on TV years later,
463
00:27:48,626 --> 00:27:51,295
she immediately reported this to the FBI.
464
00:27:52,505 --> 00:27:55,591
[reporter 3] Within 24 hours,
authorities lured Bulger outside
465
00:27:55,675 --> 00:27:56,508
and arrested him.
466
00:27:56,592 --> 00:27:58,636
And confiscated nearly 30 guns
467
00:27:58,720 --> 00:28:01,639
and hundreds of thousands of dollars
stashed in the apartment.
468
00:28:03,224 --> 00:28:05,977
[man] We have captured one of the FBI's
ten most wanted fugitives.
469
00:28:06,728 --> 00:28:09,605
A man notorious in Boston
and around the world.
470
00:28:11,899 --> 00:28:15,069
[narrator] Whitey's meticulous planning
kept him alive and out of jail
471
00:28:15,153 --> 00:28:17,572
until the ripe old age of 81,
472
00:28:18,364 --> 00:28:21,451
making him one of mob bossery's
true iron men.
473
00:28:25,872 --> 00:28:29,208
[Dick] He chose a profession,
the underworld life of crime,
474
00:28:29,792 --> 00:28:32,170
where the shelf life
isn't particularly long.
475
00:28:33,379 --> 00:28:36,466
But he managed to survive for decades.
476
00:28:41,846 --> 00:28:44,515
[narrator] But as impressive
a feat as that was,
477
00:28:45,308 --> 00:28:48,560
achieving the ultimate promise
of becoming a mob boss
478
00:28:48,644 --> 00:28:51,063
requires grander ambitions.
479
00:28:51,689 --> 00:28:54,733
For the playbook's final chapter,
480
00:28:54,817 --> 00:28:58,487
I'll show you how to harness
your criminal skills into wealth,
481
00:28:58,571 --> 00:29:03,159
power, and influence
beyond your wildest dreams.
482
00:29:05,953 --> 00:29:06,871
Your guide...
483
00:29:07,371 --> 00:29:12,710
who else but the king
of cocaine himself, Pablo Escobar.
484
00:29:15,880 --> 00:29:17,882
[theme music playing]