May 13, 2026
50 Shades of Evil: Massachusetts

In this episode of "50 Shades of Evil" Jim Chapman brings you to Massachusetts to tell the story of "Freddy" Geas who after being sentenced to life in prison, killed infamous Boston mobster "Whitey" Bulger.
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WEBVTT
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M M.
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A Wall Street line, shackle change, Oh doesome Girdy, it's
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calling my name. There is no mercy and it's been
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a tentery juice as the hill Stream game Rango three.
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I'm here but by mere to die.
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Inside these walls, inside the wild.
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Hadn't went no girls as I Hey everyone, welcome back
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in Today I am continuing this fifty Shades of Evil
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series and this time I'm going to take you to
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Massachusetts and I'm going to tell you the story of
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Freddy Gash, who in twenty eighteen orchestrated the imprison murder
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of a Boston mobster that you probably have heard of
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named Whitey Bulger. But even prior to that evil act,
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Freddy was well known as one of the most dangerous
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hit men in the mobs. So let's get into it.
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And Freddy is a lifelong criminal, having began his criminal
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activity in his early teens. He and his brother they
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had a reputation for being extremely dangerous, so feared and
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dangerous in fact, that even though he was of Greek descent,
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the Italian mafia would hire him for hits, which that
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speaks to me on how lethal this guy really was.
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The Italian mob. They didn't like to typically do business
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with non Italians. Now, this guy liked the notoriety of
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being known as a straight up killer. It appeared he
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always did, even from a young age. So let's go
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back to nineteen sixty six in Springfield, Massachusetts, where Freddy
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was born. He grew up there with his mom and dad.
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He had a younger brother named Ty, who was about
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five years Freddy's junior. Now Freddy was at actually the
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more tame of these two brothers. Ty would be the
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first to get some jail time when in nineteen eighty nine,
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at the age of seventeen, he would get into a
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serious fight outside of a McDonald's. He would go to jail,
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and this is where Ty would get introduced to a
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member of the Genevezi crime family. Now this is one
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of the five families of New York. His older brother, Freddie,
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He and Ty were pretty tight, so tight in fact,
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that Freddie would visit his brother Tye all the time
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in prison, and this would lead to Freddie also being
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introduced to members of the Genevizi crime family. Now there
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were some pretty big contrast at the time between Ty
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and Freddie. Ty really lived the life of a criminal,
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where Freddie he came off more like a family man.
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At this point, he was married with children and he
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was helping run his family's jewelry store. He didn't really
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party or go out at night, and typically just worked
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and went home to his wife and kids. But that
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was outward appearances. He definitely had crime in his blood.
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And when his brother would get released from that short
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bit in prison, he would come home and he would
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tell Freddie's stories of what life was like on the
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inside of prison, and Freddie he would really feed into this,
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almost the opposite of what I guess normal people would do,
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where you and I would say, I don't want any
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life where I don't have complete freedom. Freddie was just
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taken in by this life inside of prison. So wasn't
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too long in nineteen ninety, at the age of twenty
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three that Freddy gets into his own bit of trouble.
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He gets into a fight with a police officer and
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it was a physical fight where Freddie actually beat this
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officer up, but shockingly he gets acquitted of the charge,
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but it does kind of put him on the police radar,
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and this would lead to a bunch of issues in
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his family life. His wife would divorce him shortly after
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that incident. Then in nineteen ninety six, at the age
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of twenty nine, he really sinks deeper into crime when
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he participates in the robbery of a tractor trailer that
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was full of computer equipment with another guy, and his
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name was Gary Westerman. Now, they pull off this heist
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of all this computer equipment, but they do get caught
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shortly thereafter. And guess what, Freddy has his own four
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year prison sentence that he has to deal with. So
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unlike most people, as I told you, Freddie, he took
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well to prison. He actually enjoyed being buying bars. He
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kept up his relationship with the Genevizi crime family, and
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when he got out of prison, he had made enough
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contacts on the inside with this dark underworld that he
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started wreaking havoc on the outside of prison. So both
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brothers at this point would become what is known as
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enforcers for the mafia. The Genevizi crime family to be specific,
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the largest crime family in New York at the time.
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Now they weren't in New York, they were based in Springfield, Massachusetts,
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but that was a big mafia place as well, in
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the spring of two thousand and three, things would really
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get serious. The crime family approached Ty and Freddie about
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assisting in a hit on a Bronx union boss by
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the name of Frank Didabo. The hit was ordered over
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a dispute regarding tickets to a Tony Bennett concert. Of
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all things. Now, the boss of the Genevizi crime family,
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Artie Nigro. He claimed that he and this union boss
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were supposed to go to this concert together. They were friends,
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but the union boss never showed. So Artie he feels
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disrespected over this, and he actually orders the murder of
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the union boss. That kind of tells you how the
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mob types operate, right, So the brothers Tie and Freddie,
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along with an associate named Anthony Artillo, they were tapped
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to carry out this murder. So on May nineteenth of
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nineteen ninety three, Tie in Artillo. They wait outside on
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a city bench in front of the Diibo's apartment building
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and Freddy he was serving as the getaway driver. So
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the union boss he goes to leave the building, he
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gets in his car, he closes the door. In Artillo
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and Tie they jump on him. They approach the vehicle,
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they open fire on the driver sib window. The union
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boss has hit nine times. Freddy rolls up, he opens
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the door. Both these guys jump in and they drive
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away and they toss the guns into a nearby wooded area. However,
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this union boss would actually survive that hit. Now. He
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would later say that he knew he could take the bullets,
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and he just pulled his jacket over his head and
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he played dead as they were shooting. He got shot
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nine times, and he would spend months in a wheelchair.
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He would eventually move out of the Springfield, Massachusetts area,
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probably a good thing, and he would also leave his job,
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probably also a good thing. Now, the Genovizi Bossnigro, he
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would later tell the brothers quote, you need to get
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better at headshots. So surprisingly they weren't killed over the
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fact that they weren't able to kill this guy. But
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I'm sure the Geneviz crime boss was happy about this.
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So now Freddy, he has a real taste of this
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life by this point, and he likes the way it tastes.
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While the vast majority of your mob type figures, they
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prefer to move in silence, stay behind the scenes. They
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don't want anybody knowing they're in the mob. This guy
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had no problem letting everyone know exactly what he was
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all about, and he would embrace this life as a
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mob enforcer and he would become very feared. In the
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summer of two thousand and three, he also gets into
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a massive bar fight against a rival crew. It involved
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bats and involved guns, it even involved ice picks. Real
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mafia shit. Then on November fourth of two thousand and three,
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another hit would come down. Remember Gary Westerman, the same
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guy that Freddy pulled off that computer heist with years earlier, Well,
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he would become the victim on this one. It was
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discovered that Gary was a police informant and Freddy, along
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with his brother and two others, they lure Westerman into
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a wooded location where they beat him nearly to death.
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Then Freddy shoots him in the head and they bury
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him in a pre dug hole. Now, the body was
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never found until seven years later when one of Freddy's
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crew members he actually cooperates with the Feds, but it
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took him seven years to even find that body. Now
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back to November of two thousand and three, another hit
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comes his way. It's just two weeks after the Westerman
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hit a guy by the name of big Al Bruno.
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He was a made member of the Genavizi crime family.
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But again it was discovered this guy was also working
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with the police and the crime families at this time,
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all five families. They have problems with informants big time,
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and that would be one of the things that would
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take them down. And the only result of that if
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you're found out to be an informant is death period.
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So they find out this guy's working with the police
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even though he's made guy, they order his death and
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they tap Freddy for that hit. So Freddie he recruits
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a jail acquaintance of his by the name of Frankie Roach,
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and he pays Roach ten thousand dollars to actually conduct
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the hit. So he gets the contract for this hit,
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and then he pays someone else to actually do it,
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which Roach does. He guns down big Al in a
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parking lot in Springfield, Massachusetts after a card game. Now
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for this crime, Frankie Roach would eventually get caught by police,
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but they could a deal with him, and they say, look,
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if you agree to testify against Freddy and you say
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in open court, you admit under testimony that he is
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the one who actually paid you for this hit. You're
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going to get a very light sentence because they were
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after the bosses, right, They were after the people in
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the actual mob, not the bosses, but the guys that
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were actually either in the mob or worked very close
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to the mob, which obviously the brothers I'm talking about
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today did. And he agrees to do that. So on
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April nineteenth of two thousand and seven, Freddy gets arrested
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and he is charged in the murder of Big al Bruno.
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So he is a waiting trial on that murder, and
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that's when police discover Westerman's body in that hole for
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many years prior. So when the smoke clears in twenty eleven,
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he is convicted in both Big Awl's murder as well
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as Westerman's murder and the attempted murder of that union boss.
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Now brother he is also convicted in Westerman's murder and
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the attempted murder of that union boss, and both are
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sentenced to life in prison. So it's off to USP
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Atlanta and USP y'all stands for United States Penitentiary at
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Atlanta for Freddie. And this is a very old like
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one hundred year old prison that is pretty infamous for
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housing mobsters. Even al Capone stayed inside of this prison.
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So the mob they have crews inside of prisons the
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same way they do outside of prisons in the federal government.
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They know that, so they try to shuffle guys throughout
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the prison system as often as possible. It's no different
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for Freddie and his brother, and in twenty fifteen he
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gets moved to USP Hazelton, which is in West Virginia.
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And incidentally, of course, his brother Tie, he was never
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housed at any of the prisons that Freddy was hoigh
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that obvious reasons there, right, you don't want two brothers
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being able to coordinate an escape, for example. So Hazelton
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is where Freddy eventually gets moved. And now USP Hazelton
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is notorious for being the most dangerous prison in the
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federal system, and Freddy would fit right in inside of
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this prison. He would link up with other crew members
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from his area of Massachusetts, and he was in general population,
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so he would get into fights often. But this guy
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could handle himself. A fight did not bother him. He
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was pretty violent, if you haven't already figured that out,
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and he was down for whatever. So he's in that
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prison for a bit and he hears some news that
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was of great interest to not only himself but some
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other crew members who were housed there from Springfield, Massachusetts.
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And the news that they get is that the most
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one man in America at one point, Whitey Bulger, who
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had been captured a few years prior after a leading
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the FBI for some sixteen years, he was being transferred
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to USP Hazelton. Now Waite Bulger was no joke, y'all.
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He was the head of an Irish mob called the
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Winterhill Gang. They were based out of the Boston area,
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and he had killed nineteen people before he went on
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the run. It had actually come out in the years
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the FBI was looking for him, or at least alleged
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that he was actually working for the FBI as an informant,
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and Freddie considered him a trader to the mob and
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had a deep hatred for Boulger. Now Bulger had spent
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time in several prisons. Bulger was housed prior to Hazelton
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at what is known as USP Coleman, which is in Florida.
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Now he had been housed in that prison since twenty thirteen.
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In twenty eighteen, Bulger's health really started to decline, and
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he would have seven separate instances where he was hospitalized
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for shortness of breath. He gets placed in a special
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housing unit. This is for about eight months, after threatening
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a nurse of all things and telling her he had
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lost his will to live. Now, at this point, old
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Woody is old, very old, eighty nine years old to
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be exact, and he is confined to a wheelchair. On
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October eighteenth of twenty eighteen, the Bureau of Prisons they
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had proved a transfer to USB Hazelton. Now what's shocking
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to me here is that upon his arrival at Hazelton,
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white he is not placed in protective custody, but rather
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in general population. And the word was Whitey, even at
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eighty nine years old and in a wheelchair, thought he
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was a badass and said, fuck that, I want to
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