James “Whitey” Bulger was born to a large Irish-American Catholic family in the Old Harbor projects of South Boston. His younger brother, William, would later become president of the Massachusetts Senate for seventeen years. Bulger had early run-ins with the police as a teenager before joining the United States Air Force. After his discharge he took part in a series of bank robberies in Indiana for which he was arrested and sentenced to a twenty-year prison term. During his incarceration at a federal penitentiary, Bulger was accused of conspiring to escape and was transferred to Alcatraz Prison to serve the remainder of his sentence. Upon his release Bulger returned to South Boston, where he worked for a bookmaker before transferring his loyalties to the predominantly Irish Summer Hill Gang of Somerville, Massachusetts.
Bulger’s criminal career reached new heights after 1975 when he began a partnership with another product of the Old Harbor projects, John Connolly, who also happened to be an agent in the Federal Bureau of Investigation (FBI). Remaining mindful of the long-standing strictures against informers among the South Boston Irish, Bulger provided Connolly with information that brought successful prosecutions against Boston’s Italian mob. Connolly soon enjoyed great success in the FBI, but Bulger’s cooperation came at a price: he skillfully used the FBI to target other Irish gangsters in South Boston, and then secured special protection through his connection with the increasingly influential Connolly. Bulger and his associate, Steve “The Rifleman” Flemmi, rose to the top of the organized crime scene in Boston through a tightly organized, ruthless syndicate that even used information from Connolly to murder potential informants. Bulger’s subterranean connections soon stretched far beyond South Boston, with the murder of a Tulsa businessman and a foiled transatlantic gunrunning operation with the Irish Republican Army.
Bulger was as ruthless as he was resourceful, and he supplemented his image as a benevolent gangster in South Boston with a brutal willingness to dispatch even the most peripheral bystanders. Bulger kept his operation out of the public eye by playing off the bonds of ethnic loyalty among the marginalized residents of South Boston’s housing projects. He had a deep disdain for the ostentatious ways of his predecessors, he abstained from smoking and drinking, and he continued to reside with his mother in the Old Harbor projects, all of which helped him to cultivate the image of a loyal son of Southie. Continuing to manipulate Connolly and his supervisor, Jack Morris, Bulger maintained absolute discipline throughout his South Boston operation.
This balancing act finally ended in the early 1990s when Connolly retired and other law-enforcement agencies and the Boston federal prosecutor’s office set their sights on Bulger. Flemmi was arrested in 1995 on racketeering charges, but Bulger escaped. In 1999 a federal judge indicted Connolly on five counts, one of which stemmed from allegations that the FBI agent’s warning had allowed Bulger to narrowly avert capture by the police after 1995. Whitey Bulger’s continued flight also brought down his brother: in 2003 William Bulger resigned his position as chancellor of the University of Massachusetts system after disclosing that he had talked with his fugitive brother. Meanwhile, in South Boston, the disclosure of Bulger’s career as an informant prompted a backlash against the former crime boss, which was presented with particular poignancy in Michael MacDonald’s memoir, All Souls: A Family Story from Southie. Whitey Bulger’s legend has continued to grow as more accounts of his ruthless operations continue to surface, but Bulger has managed to evade apprehension despite being placed on the FBI’s Top 10 Most Wanted List.
BULGER, William; MacDONALD, Michael
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