An eighty nine year old man sits in a prison jumper on his wheel chair.
His hair has long since grayed and fallen out in large patches, and yet despite appearances
this old man was once one of America's most feared crime lords.
Waiting to be transferred between prisons for his next trial, the old man is sitting
in his prison cell when suddenly two large men slip inside.
They proceed to beat the man mercilessly, then they wrap him in his blanket and lay
him in his bed.
Within the hour, the old man is found by prison staff, though he has long since been dead.
So ends the life of Whitey Bulger, Boston's most notorious crime lord.
Whitey Bulger, legally known as James Joseph Bulger Jr., was born in 1929 to a Canadian
immigrant and his Irish wife.
Bulger's father worked as a union laborer in the Boston area, and occasionally as a
longshoreman- or dock worker- in Boston's harbor.
Earning a decent living, the entire family was nevertheless cast into destitution when
Bulger's father had his arm mangled in an industrial accident.
The family would end up moving to a housing project in South Boston in 1938 where Bulger
would grow up alongside two brothers, William Michael and John P. Bulger.
Yet while William and John both excelled at school, Bulger was drawn into the street life
and soon he developed a reputation as a thief and street fighter.
Local police nicknamed bulger “Whitey” because of his very blond hair, but Bulger
hated the name and preferred to be called Jim, Jimmy, or Boots due to his habit of wearing
cowboy boots and his fondness of hiding a switchblade inside them.
Like so often happens though, the name Whitey stuck, which admittedly sounds more nefarious
than being known as Boots.
In 1943 Bulger was a part of an Irish street gang known as the Shamrocks, though his criminal
activities would lead to his first arrest and sentencing to a juvenile reformatory.
After being released in 1948, Bulger did as so many other poor kids with no options do
and enlisted in the US military, joining the US Air Force.
Throughout his enlistment though he spent time in military prison for assaults and was
even arrested by Air Force police for going absent without leave in 1950.
Surprisingly he managed to finish his four year contract though and in 1952 earned an
honorable discharge and returned back home to Massachusetts.
In 1956 though Bulger was arrested for armed robbery and truck hijacking, earning his first
sting in federal prison at the Atlanta Penitentiary in Georgia.
As a way to shorten his prison sentence, Bulger volunteered for what he thought was a program
using experimental drugs to help find a cure for schizophrenia, though unfortunately for
him he was actually volunteering to join secret testing of the CIA's MK-ULTRA program.
Fearful of Communist forces overseas using drugs and other means to control the minds
of US service members, the CIA had decided it needed to beat the communists to the punch,
and therefore had launched MK-ULTRA as a means of discovering if there were any ways to influence
or control unwitting subject's minds.
For eighteen months bulger and eighteen other inmates were given a steady diet of LSD and
other mind-affecting drugs, and while that may sound like a far better way to spend time
in prison, maybe even enjoyable, Bulger would go on to describe the experience as a nightmarish
hell on earth.
His own journal showed that Bulger was terrified by the visions the drugs caused, and that
he routinely heard voices but feared that if he told anyone then he would be committed.
In November of 1962 Bulger would finally be transferred to Leavenworth Federal Penitentiary,
and then a year later to Lewisburg Federal Penitentiary, until his third parole plea
was granted in 1965.
In total Bulger would serve nine years in prison and he would not be arrested again
for another 46 years.
After his release Bulger attempted to go straight working as a Janitor and construction worker,
but ended up being lured back into the easy life of crime, becoming a bookmaker and loan
shark working under mobster Donald Killeen.
Killeen was a central south Boston crime figure who's gang, named The Killeens- no points
for style there- had ruled South Boston's criminal underground for over twenty years.
During his time with the Killeens, Bulger was caught up in the infamous Killeen-Mullen
war when Killeen's younger brother Kenny shot and mauled Michael Dwyer, a member of the
rival Mullen gang.
The war would lead to dozens of killings throughout Boston and its suburbs, and it was during
this war that Bulger drew his first blood.
Setting out to kill Mullen gang member Paul McGonagle, Buller instead mistakenly shot
McGonagle's law-abiding brother Donald square between the eyes.
As Bulger realized he was on the wrong side of a losing war, he secretly approached Howie
Winter, leader of the Winter Hill Gang- seriously, what's with these names?
Bulger told Winter that he could end the gang war by murdering the leaders of the Killeens,
and shortly after Donald Killeen was gunned down outside his home.
Some dispute that this ever happened though, and that Donald was murdered by Mullen enforcers
instead.
Whatever the case, Bulger and the surviving Killeens fled Boston, fearing for their lives.
The Killeens petitioned for Winter and Patriarca caporegime Joseph Russo to mediate a ceasefire
between the two gangs.
Bulger represented the Killeens and the two gangs ended up joining forces under Winter
as overall boss.
With a truce in place in 1972, Bulger shared control of South Boston's criminal underworld
with the Mullens.
Bulger then began shaking down bookmakers and loan sharks, and in order to remove opposition,
he petitioned Winter to sanction the murder of anyone who stepped out of line.
Bulger used this sanctioned killing to remov e all would-be competition from South Boston.
In 1979 though lady luck would smile once more on Bulger as Winter and his inner circle
were arrested on charges of fixing horse races.
Stepping into the power vacuum alongside his top lieutenant Stephen Flemmi, Bulger took
over leadership of the gang and transferred its headquarters to the Lancaster Street Garage
near the Boston Garden in the West End.
Flemmi however had been an FBI informant since 1965, and in 1971 the FBI had approached Bulger
and attempted to recruit him as well, though they failed to earn his trust.
Eventually though Bulger followed in Flemmi's footsteps and became an informant, and though
the exact circumstances remain unclear, it's believed that he did so in exchange for aid
from the FBI against the Patriarca, a powerful italian mafia with whom Bulger had an ongoing
feud.
According to FBI agent John Connolly, when told that the FBI would help in his feud,
Bulger responded by saying, “Alright, if they want to play checkers, we'll play chess.
Fuck 'em.”
Other sources however claim that Bulger was in effect blackmailed into becoming an informant
by the FBI, who threatened to send him back to prison if he didn't cooperate.
The mafia story was merely a cover meant to explain Bulger and Flemmi's status as informants.
Whatever the case, Bulger and Flemmi used their status as informants to remove competition,
ratting out other criminal figures who would be conveniently pinched and jailed.
Inner threats were also removed this way, and any gang member who threatened Bulger's
status as boss would quickly find himself locked up in prison.
Bulger's main targets though were the italian Patriarca family, and in 1986 indictments
against its prominent leaders left the Patriarca operation in Boston in complete shambles.
Bulger was all too happy to step in and fill the void, so while the FBI had gotten rid
of a major criminal threat, it had merely facilitated the creation of a brand new one.
Throughout the 80's Bulger's power grew and his operations expanded throughout all of
eastern Massachusetts.
He routinely engaged in extortion, loansharking, bookmaking, truck hijackings, and even arms
trafficking.
While state and federal agencies fiercely pursued Bulger and his associates, Bulger's
fear of wiretappings made it difficult to obtain good intel on their operations, as
he was very careful to never discuss business over a phone or inside a vehicle that could
have been potentially bugged.
South Boston's strict code of silence amongst its criminals also protected Bulger and his
operations, the fear of being executed as a rat far greater than fear of law enforcement.
However it was corrupt police and FBI contacts that Bulger had cultivated that ultimately
made him almost untouchable, with his own FBI handler, Special Agent John Connolly,
helping keep Bulger out of the sights of law enforcement.
Yet Bulger would go on to say that even more important than Connolly was Massachusetts
State Police Lieutenant Richard J Schneiderhan, who consistently tipped Bulger off on investigations
and possible raids.
While loansharking, theft, and extortion were Bulger's favorite crimes, the mid-1980s saw
him expand into the drug trade.
At first bulger would summon drug dealers to meet with him, and there he would reveal
that he had been offered a substantial sum of money for their murder.
This was a ruse of course, but the scared dealers would happily pay a large amount of
money for their life.
Eventually though as America's love with illegal drugs deepened and profits grew to incredible
levels, Bulger made his move to enter the drug trade himself.
At the time most of South Boston's drugs were under the control of a crew led by mobster
John Shea, and Bulger briefly considered simply killing Shea and taking over the operation
himself.
Instead though he decided to rule from afar by extorting Shea's operation, and taking
a cut of his weekly profits while enforcing his own rules on the entire drug trade.
Bulger strictly enforced that any dealers operating in South Boston would not sell PCP-
likely due to his own experiences with the CIA's mind-affecting substances- and that
they were not to sell to children.
Any drug dealer not operating under Bulger's rules would be very violently driven from
“The Town” as South Boston came to be known.
Bulger also frequently engaged in arms trafficking, in support of the IRA during The Troubles
in the 1990s, where the Irish violently opposed the British occupation of Northern Ireland.
A lifelong supporter, Bulger made it clear to the FBI that he would never betray the
IRA, and he routinely shipped weapons and blocks of C-4 to the revolutionary organization.
On at least one of those shipments though IRA members mistakenly burned down the van
that contained a whole shipment of donated weapons and explosives.
During a trip to Ireland, a crew member aboard the freighter shipping some of Bulger's donated
weapons was arrested by the FBI.
This crew member implicated Bulger in the shipment, though Bulger's FBI handler, John
Connolly, overheard the implication.
Shortly after the crew member was discovered dead, murdered by Bulger.
Initially not wanting to murder the crew member though, Bulger had planned to send him to
South America with money and the understanding that he was never to contact this family or
friends ever again.
During the course of his interrogation though, Bulger decided that the crew member lacked
the discipline to cut ties with everyone in his life, and decided to murder him instead.
Bulger's crime spree would come to an end in 1994 when an investigation launched by
the DEA, Massachusetts State Police, and the Boston Police Department was aimed at Bulger
and his operations.
Knowing that the FBI had been compromised, the agency was never informed.
Bulger would go on to flee Boston and stay on the run for an incredible sixteen years,
having spent twelve of those years at the number two spot on the FBI's most wanted list,
just under Osama Bin Laden.
Shortly after his capture, James Joseph Whitey Bulger would be murdered in prison at the
behest of the mafia, the killing carried out by a contract killer on a life sentence and
a second associate.
After a life of ruling over east Massachusetts criminal underworld, Whitey Bulger was ultimately
beaten to death in a jail cell.
After hearing all this, do you think crime ever truly pays?
Is it worth all the money to spend your entire life looking over your shoulder?
Also, be sure to check out our other video America's Most EVIL Serial Killer - Ted Bundy.
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