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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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{\an8}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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{\an8}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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{\an8}Bulger, by far,
has to be the most notorious
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{\an8}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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{\an8}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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{\an8}Whitey Bulger, he grew up
in poverty in South Boston.
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{\an8}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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{\an8}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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{\an8}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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{\an8}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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{\an8}Steve Flemmi and Johnny Martorano.
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{\an8}[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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{\an8}And in that sense,
they had the right stuff, the résumé
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{\an8}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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{\an8}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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{\an8}he relied on hitman Roy DeMeo
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{\an8}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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{\an8}through an old friend.
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{\an8}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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00:14:12,518 --> 00:14:17,398
Bulger protected him from some fistfight
years ago, and as a result,
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00:14:17,481 --> 00:14:21,110
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
238
00:14:32,204 --> 00:14:35,207
to discuss rekindling the relationship.
239
00:14:36,083 --> 00:14:38,752
Connolly's convinced
that getting an in with the gangster
240
00:14:38,836 --> 00:14:43,340
would transform his career,
while Whitey has his own agenda,
241
00:14:43,424 --> 00:14:46,176
VIP treatment from the local FBI.
242
00:14:47,219 --> 00:14:49,138
He begins feeding Connolly tips
243
00:14:49,221 --> 00:14:51,849
on his rivals
inside the Boston underworld,
244
00:14:52,975 --> 00:14:56,353
so federal agents
can do his dirty work for him.
245
00:14:59,690 --> 00:15:04,278
Whitey is credited with helping the feds
nab their most coveted prize,
246
00:15:04,361 --> 00:15:07,781
the head of Boston's Italian Mafia,
Jerry Angiulo...
247
00:15:07,865 --> 00:15:09,074
[camera shutters clicking]
248
00:15:09,158 --> 00:15:12,244
...by securing inside information
about Angiulo's headquarters,
249
00:15:12,328 --> 00:15:14,705
which they used to set up wiretaps.
250
00:15:16,332 --> 00:15:20,628
It leads to a successful takedown
of the entire Angiulo crime family.
251
00:15:20,711 --> 00:15:21,545
[siren wailing]
252
00:15:21,629 --> 00:15:26,258
With the Mafia sidelined,
Whitey becomes even more powerful.
253
00:15:27,343 --> 00:15:31,513
Connolly also keeps
Whitey's name off of official FBI reports
254
00:15:31,597 --> 00:15:33,724
and tips him off about investigations.
255
00:15:35,225 --> 00:15:38,020
It's a profitable relationship all around.
256
00:15:39,521 --> 00:15:42,775
And as the line between
criminal and cop begins to blur,
257
00:15:43,275 --> 00:15:46,820
Whitey himself becomes nearly untouchable.
258
00:15:47,613 --> 00:15:50,491
[Dick] I don't think
in the history of American crime
259
00:15:50,574 --> 00:15:54,119
there's anyone who achieved
what Whitey Bulger achieved
260
00:15:54,203 --> 00:15:56,914
when it came to having
corrupt law enforcement
261
00:15:56,997 --> 00:15:58,999
feeding you valuable intel.
262
00:15:59,083 --> 00:16:00,250
[siren wailing]
263
00:16:00,334 --> 00:16:03,295
[Emily] So many people
in law enforcement were going crazy
264
00:16:03,379 --> 00:16:05,714
trying to get Bulger on something.
265
00:16:06,966 --> 00:16:10,386
Everybody wondered, "How does he know?
It seems like he knows what we're doing."
266
00:16:10,469 --> 00:16:12,388
Sometimes that's 'cause he did.
267
00:16:13,764 --> 00:16:17,601
[narrator] But while sharing secrets
with the feds can preserve your freedom,
268
00:16:17,685 --> 00:16:21,230
it's not going to win
many friends among your peers.
269
00:16:21,981 --> 00:16:23,899
No one likes a rat.
270
00:16:24,775 --> 00:16:27,695
How do you keep
your dirty secret from coming out?
271
00:16:33,575 --> 00:16:37,287
[Dick] Whitey had a reputation
as the ultimate stand-up guy.
272
00:16:37,371 --> 00:16:40,207
Someone who doesn't talk
to the authorities.
273
00:16:40,290 --> 00:16:41,792
Doesn't give anybody up.
274
00:16:41,875 --> 00:16:45,212
Doesn't give any information,
no matter what the circumstances,
275
00:16:45,295 --> 00:16:47,923
no matter what the threat,
no matter what the pressure.
276
00:16:48,007 --> 00:16:50,092
You stand up and say nothing.
277
00:16:50,759 --> 00:16:52,886
{\an8}[narrator] Of course,
Whitey's actual relationship
278
00:16:52,970 --> 00:16:55,723
{\an8}with law enforcement was more complicated.
279
00:16:56,765 --> 00:16:58,726
Whitey always had to be on his guard,
280
00:16:58,809 --> 00:17:01,562
always, 'cause he was
living a double life.
281
00:17:03,147 --> 00:17:06,567
The underworld had no idea he was a rat.
282
00:17:07,401 --> 00:17:11,780
So, he was always living with that.
He knew what would happen if we found out.
283
00:17:13,323 --> 00:17:14,616
[narrator] Need more proof?
284
00:17:14,700 --> 00:17:17,202
See what happened
to these other chatty dons.
285
00:17:19,705 --> 00:17:23,375
Big Jack Zelig,
boss of Manhattan's Eastman Gang,
286
00:17:23,459 --> 00:17:25,252
got knocked off in 1912
287
00:17:25,335 --> 00:17:28,672
while riding the Second Avenue trolley
after his people learned
288
00:17:28,756 --> 00:17:31,675
he was in the pocket
of a corrupt NYPD lieutenant.
289
00:17:32,468 --> 00:17:36,305
Chicago crime boss James Ragen
was ambushed and shot after exposing
290
00:17:36,388 --> 00:17:39,141
the top echelon
of the Chicago mob to the feds.
291
00:17:39,767 --> 00:17:43,020
While recovering in the hospital,
he identified the gunman
292
00:17:43,103 --> 00:17:46,065
and was summarily murdered
via mercury poisoning.
293
00:17:46,815 --> 00:17:49,485
And Bonanno family captain,
Dominick Napolitano,
294
00:17:49,568 --> 00:17:53,238
got whacked for allowing
FBI agent Joseph Pistone,
295
00:17:53,322 --> 00:17:56,825
aka Donnie Brasco,
to infiltrate the family.
296
00:17:57,409 --> 00:17:59,536
He was ultimately found
with his hands cut off,
297
00:17:59,620 --> 00:18:02,956
a traditional penalty
for divulging Mafia secrets.
298
00:18:07,503 --> 00:18:11,340
When it came to protecting
Whitey Bulger's stand-up image,
299
00:18:11,423 --> 00:18:14,134
his homicidal reputation came in handy.
300
00:18:14,218 --> 00:18:15,844
No one suspected someone
301
00:18:15,928 --> 00:18:19,932
as dangerous as him
to be a top FBI informant,
302
00:18:20,015 --> 00:18:21,725
basically ratting on other people
303
00:18:21,809 --> 00:18:24,353
to enhance his position,
increase his power.
304
00:18:24,436 --> 00:18:27,731
There had been rumors,
but most people scoffed at the rumors
305
00:18:27,815 --> 00:18:29,650
because it was too ridiculous.
306
00:18:30,651 --> 00:18:35,114
[narrator] To keep it that way,
nothing and no one was off-limits.
307
00:18:38,617 --> 00:18:43,372
Debra Davis is the longtime mistress
of Steve Flemmi, Whitey's right-hand man.
308
00:18:43,956 --> 00:18:46,542
Generally,
Whitey doesn't pay her much mind
309
00:18:47,459 --> 00:18:50,212
until she catches wind of Whitey's secret
310
00:18:50,295 --> 00:18:52,965
that he's been working
with the FBI for years.
311
00:18:53,590 --> 00:18:56,969
Flemmi, who has developed
his own FBI connection,
312
00:18:57,052 --> 00:19:00,430
tells Whitey everything's under control.
313
00:19:01,056 --> 00:19:02,933
Whitey isn't convinced.
314
00:19:03,517 --> 00:19:07,312
And when Flemmi and Debra's relationship
starts to hit the rocks,
315
00:19:07,396 --> 00:19:09,398
the risk becomes untenable.
316
00:19:12,401 --> 00:19:14,611
Whitey has Flemmi set a trap,
317
00:19:14,695 --> 00:19:18,699
telling Debra he wants to show her
a house he wants to buy for her.
318
00:19:19,741 --> 00:19:21,785
But when Flemmi gives her a tour,
319
00:19:22,411 --> 00:19:25,247
she ends up
with a different sort of closing.
320
00:19:27,791 --> 00:19:31,211
[woman screaming]
321
00:19:31,712 --> 00:19:33,088
[narrator] Cleanup is quick
322
00:19:33,922 --> 00:19:34,922
and thorough.
323
00:19:37,634 --> 00:19:40,596
They bury Debra
next to Tommy King on Tenean Beach.
324
00:19:42,306 --> 00:19:45,809
And just like that,
Whitey's secret stays hidden.
325
00:19:46,810 --> 00:19:50,189
This guy had no empathy
for anybody, only for himself.
326
00:19:50,272 --> 00:19:52,107
He didn't care for no one, this guy.
327
00:19:52,191 --> 00:19:53,525
They killed women.
328
00:19:54,151 --> 00:19:55,777
They killed innocent people.
329
00:19:55,861 --> 00:19:58,197
It was amazing,
the things he was capable of doing
330
00:19:58,280 --> 00:20:02,075
in the name of his security
and his freedom.
331
00:20:02,743 --> 00:20:04,983
[narrator] But even if you take
all the right precautions
332
00:20:05,621 --> 00:20:07,915
and have all the right protection,
333
00:20:07,998 --> 00:20:10,292
no one stays untouchable forever.
334
00:20:10,792 --> 00:20:13,629
When the tide turns, you need to be ready.
335
00:20:14,213 --> 00:20:16,256
Let the playbook show you the way.
336
00:20:21,845 --> 00:20:24,473
[Brian] When a mob boss
wants to evade justice,
337
00:20:25,057 --> 00:20:28,018
many of them
have to eventually go on the run.
338
00:20:30,437 --> 00:20:33,899
But that's difficult to do
if you're not disciplined.
339
00:20:34,691 --> 00:20:35,943
[narrator] But as we've seen...
340
00:20:36,026 --> 00:20:37,027
Need a little grass?
341
00:20:37,110 --> 00:20:39,446
[narrator] ...discipline was
Whitey's middle name.
342
00:20:39,529 --> 00:20:40,529
No, thanks.
343
00:20:41,907 --> 00:20:45,619
[man] Whitey was always
in full control of his environment.
344
00:20:45,702 --> 00:20:47,079
I've never seen him drink.
345
00:20:47,579 --> 00:20:50,290
He never socialized.
He didn't mix with people.
346
00:20:50,958 --> 00:20:53,585
That's a vulnerability
if you're doing the wrong thing.
347
00:20:54,628 --> 00:20:57,506
[Brian] He was often thinking about,
"Well, what if I do get charged?"
348
00:20:57,589 --> 00:20:58,799
"I should be prepared."
349
00:21:01,510 --> 00:21:05,847
Whitey had been planning for years
for the curtain to fall on his show.
350
00:21:06,932 --> 00:21:09,393
He had a well-planned escape route
351
00:21:09,476 --> 00:21:12,604
where he could completely
drop off the face of the Earth.
352
00:21:14,940 --> 00:21:17,401
[narrator] The Whitey Bulger method
for getting out of Dodge
353
00:21:17,484 --> 00:21:20,946
consists of a few key steps
that any outlaw can follow.
354
00:21:21,446 --> 00:21:23,907
Step one, start saving early.
355
00:21:24,741 --> 00:21:29,788
Stash cash, jewelry, and fake passports
in safe deposit boxes all over the globe.
356
00:21:30,539 --> 00:21:33,041
Step two, build aliases.
357
00:21:34,293 --> 00:21:36,878
Pay top dollar
for fake IDs, birth certificates,
358
00:21:36,962 --> 00:21:38,714
and credit cards in various names,
359
00:21:39,548 --> 00:21:42,384
then use new identities
to open bank accounts.
360
00:21:43,552 --> 00:21:46,722
Step three, find the perfect hiding place.
361
00:21:47,389 --> 00:21:50,100
Choose somewhere you can easily blend in,
362
00:21:50,183 --> 00:21:53,020
some place with turnover and tourism.
363
00:21:54,354 --> 00:21:57,774
Outsiders will be less likely
to take note of your quirks.
364
00:21:59,234 --> 00:22:02,654
Once you've found your new hometown,
it's onto the next step.
365
00:22:02,738 --> 00:22:03,572
[shushing]
366
00:22:03,655 --> 00:22:08,368
[narrator] Tell no one when,
where, or how you're leaving.
367
00:22:09,369 --> 00:22:12,372
You'd be surprised
how many people forget this one.
368
00:22:13,290 --> 00:22:15,751
Finally, it's time to make your getaway.
369
00:22:17,002 --> 00:22:18,002
But when you do,
370
00:22:18,045 --> 00:22:21,882
don't forget the most important rule
of all for going underground,
371
00:22:22,382 --> 00:22:24,009
be ready for anything.
372
00:22:27,387 --> 00:22:30,182
{\an8}[narrator] For 20 years,
Whitey's guardian angel and the FBI
373
00:22:30,265 --> 00:22:32,601
{\an8}had kept him safe from prosecution.
374
00:22:32,684 --> 00:22:37,230
{\an8}But by the early 1990s,
Whitey's luck was starting to run out.
375
00:22:37,314 --> 00:22:38,732
[camera shutters clicking]
376
00:22:39,900 --> 00:22:45,655
In the early 1990s, we began
an investigation of Bulger and his group.
377
00:22:46,239 --> 00:22:50,994
Ultimately, we had enough evidence
to charge him with racketeering,
378
00:22:51,078 --> 00:22:52,788
along with several other individuals.
379
00:22:52,871 --> 00:22:55,916
The FBI, of course,
knew we were seeking the indictment.
380
00:22:57,292 --> 00:23:00,462
{\an8}[narrator] Whitey's top ally,
Steve Flemmi, is quickly arrested.
381
00:23:01,421 --> 00:23:05,884
It is a state trooper and a DEA agent
who captured Flemmi.
382
00:23:06,635 --> 00:23:11,640
And then the others went over
to South Boston trying to find Whitey,
383
00:23:11,723 --> 00:23:13,308
but it was to no avail.
384
00:23:13,392 --> 00:23:14,643
He was long gone.
385
00:23:15,560 --> 00:23:17,896
[narrator] Now, how do you think
that happened?
386
00:23:19,106 --> 00:23:20,982
Bulger was tipped off by Connolly,
387
00:23:22,067 --> 00:23:25,362
and he was able to take off
before the indictment came down.
388
00:23:29,074 --> 00:23:31,827
{\an8}[Brian] It was enormously frustrating
to work on a case
389
00:23:31,910 --> 00:23:35,080
{\an8}which the main target
disappears into the mist.
390
00:23:35,163 --> 00:23:36,665
{\an8}So, the strong message is
391
00:23:36,748 --> 00:23:40,419
{\an8}that law enforcement
will continue the effort until we get him.
392
00:23:40,502 --> 00:23:43,004
[newscaster] And while
his whereabouts are a mystery,
393
00:23:43,088 --> 00:23:46,466
Whitey Bulger's victims
have been turning up all over Boston.
394
00:23:47,217 --> 00:23:49,428
[man] My thoughts were,
they're not gonna find him.
395
00:23:49,511 --> 00:23:51,096
I know how he prepares.
396
00:23:51,972 --> 00:23:54,349
[narrator] It's one thing
to make a clean getaway.
397
00:23:55,392 --> 00:23:59,604
Staying safe for the long haul
will take genius-level execution.
398
00:24:00,105 --> 00:24:01,648
So, follow the master.
399
00:24:09,990 --> 00:24:14,202
When you've made a name for yourself
as one of history's top mob bosses,
400
00:24:14,286 --> 00:24:17,789
authorities won't be so quick
to let you just disappear.
401
00:24:18,331 --> 00:24:21,001
So much about being a mob boss
is being somebody.
402
00:24:21,084 --> 00:24:23,336
You have to be at ease
403
00:24:23,420 --> 00:24:27,466
and make a transition
to being unrecognized and unacknowledged,
404
00:24:27,549 --> 00:24:28,925
to being a nobody.
405
00:24:29,718 --> 00:24:32,345
[reporter] Whitey Bulger,
a known master of disguise,
406
00:24:32,429 --> 00:24:35,015
has not been seen in six years.
407
00:24:35,098 --> 00:24:39,186
The trail is cold, even though
there's a one million dollar reward out
408
00:24:39,269 --> 00:24:41,688
for information leading to his arrest.
409
00:24:43,148 --> 00:24:45,150
[Brian] Even members
of law enforcement in Boston
410
00:24:45,233 --> 00:24:46,818
couldn't tell you what he looked like.
411
00:24:48,111 --> 00:24:51,698
In fact, he probably looked like
half the people at Fenway Park.
412
00:24:53,575 --> 00:24:55,952
[narrator] But even if people
don't know your face,
413
00:24:56,495 --> 00:24:59,706
keeping yourself off the radar
will be a full-time job.
414
00:25:00,207 --> 00:25:03,543
Whitey excelled
at this second career as well.
415
00:25:06,129 --> 00:25:07,756
After crossing the country,
416
00:25:07,839 --> 00:25:12,511
Whitey and his longtime girlfriend,
Catherine Greig, settle in Santa Monica,
417
00:25:12,594 --> 00:25:15,597
where they take the names
Charlie and Carol Gasko.
418
00:25:16,515 --> 00:25:19,434
Just a harmless retiree
and his loving wife,
419
00:25:19,518 --> 00:25:23,438
living in a rent-stabilized
apartment building near the Pacific Ocean.
420
00:25:24,105 --> 00:25:28,401
They were your typical snowbirds
from the East Coast,
421
00:25:28,485 --> 00:25:29,986
living in a warm climate,
422
00:25:30,070 --> 00:25:33,156
and, you know,
not causing any problems for anyone.
423
00:25:35,200 --> 00:25:37,160
[narrator] Tenants in their building
are friendly,
424
00:25:37,202 --> 00:25:39,829
but the Gaskos choose
to keep their distance,
425
00:25:40,372 --> 00:25:42,123
especially Charlie.
426
00:25:43,583 --> 00:25:48,171
However, there are some people
he makes a point of seeking out.
427
00:25:48,755 --> 00:25:51,925
[Brian] Bulger would befriend
homeless people
428
00:25:52,008 --> 00:25:56,638
or people really in desperate situations,
and he would pay them for their ID.
429
00:25:56,721 --> 00:25:58,431
For Bulger, it was like gold.
430
00:25:58,932 --> 00:26:02,060
[narrator] Whitey would tell them
he's an illegal immigrant from Canada
431
00:26:02,143 --> 00:26:03,562
in need of medical help
432
00:26:04,104 --> 00:26:06,106
and offer to pay hundreds of dollars
433
00:26:06,189 --> 00:26:09,317
for their driver's license
and social security number.
434
00:26:10,569 --> 00:26:11,653
Most agree.
435
00:26:13,572 --> 00:26:14,990
To avoid being tracked,
436
00:26:15,073 --> 00:26:19,119
Whitey and Catherine rotate identities
at dental and medical appointments.
437
00:26:20,078 --> 00:26:24,499
And when they cross into Tijuana
to buy Whitey's heart medication,
438
00:26:25,083 --> 00:26:27,168
authorities pay no mind.
439
00:26:28,670 --> 00:26:31,089
Everybody just sees
Charlie and Carol Gasko
440
00:26:31,172 --> 00:26:34,676
enjoying their golden years
by the California coast.
441
00:26:36,261 --> 00:26:39,973
The perfect cover for the perfect couple.
442
00:26:44,102 --> 00:26:47,689
For 16 sun-soaked years, Charlie...
443
00:26:47,772 --> 00:26:51,359
I mean, Whitey, lived his best life
444
00:26:51,443 --> 00:26:55,071
as authorities continued their efforts
to track him down.
445
00:26:55,155 --> 00:26:57,407
[Emily] The greatest escape
in mob history.
446
00:26:58,325 --> 00:26:59,743
It has to be up there, right?
447
00:27:00,619 --> 00:27:03,705
[narrator] But despite
Whitey's extraordinary efforts,
448
00:27:03,788 --> 00:27:05,957
the dream didn't last forever.
449
00:27:06,041 --> 00:27:08,335
We begin this morning
with a bombshell arrest overnight...
450
00:27:08,418 --> 00:27:10,712
[reporter 1] After spending 16 years
on the run,
451
00:27:10,795 --> 00:27:12,631
the FBI has caught Boston mob boss...
452
00:27:12,714 --> 00:27:14,191
[reporter 2] ...James "Whitey" Bulger
453
00:27:14,215 --> 00:27:16,301
is captured
in a Santa Monica apartment house,
454
00:27:16,384 --> 00:27:19,638
ending a worldwide manhunt
that spanned 16 years.
455
00:27:19,721 --> 00:27:21,556
[Brian] Ultimately, Bulger was captured
456
00:27:21,640 --> 00:27:24,934
in large part
because of a cat, of all things.
457
00:27:28,188 --> 00:27:31,650
There was a woman
who was watching TV in Iceland,
458
00:27:31,733 --> 00:27:34,736
and she spent her winters in Santa Monica.
459
00:27:34,819 --> 00:27:38,406
And she had bonded
with another woman over a cat.
460
00:27:38,490 --> 00:27:41,534
They were both cat lovers.
This was Catherine Greig.
461
00:27:42,452 --> 00:27:44,204
The two of them were friends.
462
00:27:44,287 --> 00:27:48,500
And when she saw
Bulger and Greig on TV years later,
463
00:27:48,583 --> 00:27:51,252
she immediately reported this to the FBI.
464
00:27:52,462 --> 00:27:55,548
[reporter 3] Within 24 hours,
authorities lured Bulger outside
465
00:27:55,632 --> 00:27:56,466
and arrested him.
466
00:27:56,549 --> 00:27:58,593
And confiscated nearly 30 guns
467
00:27:58,677 --> 00:28:01,596
and hundreds of thousands of dollars
stashed in the apartment.
468
00:28:03,181 --> 00:28:05,934
[man] We have captured one of the FBI's
ten most wanted fugitives.
469
00:28:06,685 --> 00:28:09,562
A man notorious in Boston
and around the world.
470
00:28:11,856 --> 00:28:15,026
[narrator] Whitey's meticulous planning
kept him alive and out of jail
471
00:28:15,110 --> 00:28:17,529
until the ripe old age of 81,
472
00:28:18,321 --> 00:28:21,408
making him one of mob bossery's
true iron men.
473
00:28:25,829 --> 00:28:29,165
[Dick] He chose a profession,
the underworld life of crime,
474
00:28:29,749 --> 00:28:32,127
where the shelf life
isn't particularly long.
475
00:28:33,336 --> 00:28:36,423
But he managed to survive for decades.
476
00:28:41,803 --> 00:28:44,472
[narrator] But as impressive
a feat as that was,
477
00:28:45,265 --> 00:28:48,518
achieving the ultimate promise
of becoming a mob boss
478
00:28:48,601 --> 00:28:51,020
requires grander ambitions.
479
00:28:51,646 --> 00:28:54,691
For the playbook's final chapter,
480
00:28:54,774 --> 00:28:58,445
I'll show you how to harness
your criminal skills into wealth,
481
00:28:58,528 --> 00:29:03,116
power, and influence
beyond your wildest dreams.
482
00:29:05,910 --> 00:29:06,910
Your guide...
483
00:29:07,328 --> 00:29:12,667
who else but the king
of cocaine himself, Pablo Escobar.
484
00:29:15,837 --> 00:29:17,839
[theme music playing]