Trouble from day 1
Bulger was a troublemaker as a child, and even lived out the childhood fantasy of running away with the circus when he was 10 years old. As a youth, he was arrested for larceny, forgery, assault and battery, and armed robbery and served five years in a juvenile reformatory. |
bulger's story
Press play on the video below for a brief overview of Whitey Bulger's life.
The video above is from CNN, 2014.
He might not have looked very intimidating, might not have sounded very intimidating but people knew that if you crossed Whitey you didn’t last very long."
-Shelley Murphy in Interview
His rise to Untouchable power
From Learning From the Best
Donnie Killeen led the group and say to it that Whitey came under the tutelage of his top enforcer, Billy O'Sullivan. Billy O, as he was known, was an ex-marine, someone who was quick with his fists and quicker with his gun. As soon would be the case with his protégé... Billy O was a gifted teacher. He taught Whitey how to follow his prey unobserved and, just as important, how to lose a tail." Whitey would in later years profess a debt for all that Billy O had taught him." |
to The Killeen-Mullen Truce
Donnie Killeen was dead. Kenny Killeen had no intention of meeting his brother's fate and had suddenly retired. That left Whitey Bulger as the de facto leader of what was left of the Killeen gang. And it was Whitey who sought out Howie Winter to mediate the truce with the Mullens." Howie Winter anointed him the leader of the Southie faction, and, as a result, Whitey became partners with Howie Winter, Joe McDonald, Jimmy Sims and John Martorano- the real muscle of the Winter Hill. Howie Winter liked Whitey... and now with his blessing, Whitey would lord it over Southie for the Hill. |
Final Takeover of the Winter HIll
In 1979, Howie Winter, along with 20 other members and jockeys were arrested for fixing horse races. Bulger got off of the charges due to his tie to the FBI, allowing him to take full control of South Boston.
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He and Flemmi were partners, but Whitey emerged as the leader of this South Boston based gang... He was a leader. He was the boss. He controlled everything that came in and out of Southie. People were terrified of him. He was very manipulative. People said if he wanted you to like him, you would like him. Usually there was something in it for him. If he was nice to someone, it’s usually because he wanted something... He ruled by intimidation and fear. There’s no doubt he was the boss." |
Bulger and chief lieutenant Steve "The Rifleman" Flemmi were never indicted. The reason, it was later alleged, was that they were being protected by the FBI because they were working as informants.
-Bill Finley
A soft spot
Despite being a notorious gangster, Bulger showed his leadership characteristics in another strong way, as a father.
He was protective and loyal to his little boy, Douglas, until his death from Reye's disease at age 6.
He was protective and loyal to his little boy, Douglas, until his death from Reye's disease at age 6.
[Lindsey] described the gangster as a nervous but warm and attentive father, who lavished gifts and time on the little boy, to the extent his demanding criminal schedule allowed. |
When he died, Jimmy was out of his mind, tears were streaming down Jimmy’s face.’’ |