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.
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.
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.
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.
For the last 16 years, the notorious Boston mob boss was a ghost.
Let Whitey show you how to go the distance
by never getting caught unprepared.
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.
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.
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.
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.
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.
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.
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.
Attention!
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.
For most of Whitey's run, that center included just two key allies.
Steve Flemmi and Johnny Martorano.
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.
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.
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.
Whitey and Tommy never quite hit it off.
Both of you go to hell!
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.
Whitey gets behind a propaganda machine.
He's good at this too. Selling a story.
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.
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.
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.
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.
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.
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.
Whitey has a few go-to spots
that he returns to to conduct his business.
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.
No!
It soon earns a nickname, the Haunty...
...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.
He needs to move.
So, Whitey picks an appropriate night for his ghoulish plan...
and brings along an associate to help.
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.
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.
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.
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.
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...
...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.
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.
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.
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.
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?
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.
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.
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.
To keep it that way, nothing and no one was off-limits.
Debra Davis is the longtime mistress of Steve Flemmi, Whitey's right-hand man.
Generally, Whitey doesn't pay her much mind
until she catches wind of Whitey's secret
that he's been working with the FBI for years.
Flemmi, who has developed his own FBI connection,
tells Whitey everything's under control.
Whitey isn't convinced.
And when Flemmi and Debra's relationship starts to hit the rocks,
the risk becomes untenable.
Whitey has Flemmi set a trap,
telling Debra he wants to show her a house he wants to buy for her.
But when Flemmi gives her a tour,
she ends up with a different sort of closing.
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.
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.
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.
But as we've seen...
Need a little grass?
...discipline was Whitey's middle name.
No, thanks.
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.
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.
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.
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.
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.
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.
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.
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.
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.
And while his whereabouts are a mystery,
Whitey Bulger's victims have been turning up all over Boston.
My thoughts were, they're not gonna find him.
I know how he prepares.
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.
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.
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.
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.
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.
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.
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.
The greatest escape in mob history.
It has to be up there, right?
But despite Whitey's extraordinary efforts,
the dream didn't last forever.
We begin this morning with a bombshell arrest overnight...
After spending 16 years on the run,
the FBI has caught Boston mob boss...
...James "Whitey" Bulger
is captured in a Santa Monica apartment house,
ending a worldwide manhunt that spanned 16 years.
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.
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.
We have captured one of the FBI's ten most wanted fugitives.
A man notorious in Boston and around the world.
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.
He chose a profession, the underworld life of crime,
where the shelf life isn't particularly long.
But he managed to survive for decades.
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.