Whitey Bulger

Whitey Bulger (born September 3, 1929, Dorchester, Massachusetts, U.S.—died October 30, 2018, U.S. Penitentiary Hazelton, Bruceton Mills, West Virginia) was an American crime boss who, as head of the Boston-area Winter Hill Gang, was a leading figure in organized crime from the late 1960s to the mid-1990s. For more than a decade, until his capture in June 2011, he was listed by the Federal Bureau of Investigation (FBI) as one of its 10 most-wanted fugitives.

Bulger was born to working-class Irish immigrants and grew up in a housing project in the neighbourhood of South Boston. In his early years he earned the enduring nickname “Whitey” on account of his whitish blond hair. An unruly youth, Bulger was involved in a street gang as a teenager and was arrested several times, on charges ranging from forgery to assault and battery. However, he always managed to elude any serious consequences for his wrongdoing, which nurtured in him a sense of entitlement and invincibility. In 1948 he enlisted in the U.S. Air Force. Despite a record of disciplinary problems while in the service—which included a rape charge in Great Falls, Montana—his discharge four years later was certified as honourable.

Bulger soon resumed his criminal activities, and in 1956 he was convicted for a string of bank robberies committed in three states. Although sentenced to 20 years in federal prison, he was granted parole in 1965 following stints at such notorious penitentiaries as Leavenworth and Alcatraz. Upon his return to Boston, Bulger became an enforcer for mob kingpin Donald Killeen, and in the early 1970s he took on similar duties with the Winter Hill Gang, a predominantly Irish American crime syndicate led by Howie Winter.

In 1975 Bulger agreed to work with the FBI as a so-called “Top Echelon Informant.” His FBI handler was another son of South Boston, John J. Connolly, who was about 10 years younger than Bulger and who had grown up idolizing him along with Bulger’s brother, William, who became a powerful Massachusetts politician. The informant relationship quickly turned corrupt, becoming what was later described as a “devil’s deal” and giving rise to the worst informant scandal in FBI history. Instead of the FBI controlling Bulger, the crime boss began to manipulate his handler and other FBI agents. In 1979 Bulger managed to avoid being named in an indictment for fixing horse races at tracks up and down the East Coast, a case that eventually led to the conviction of Winter and several of his associates. The resulting power vacuum allowed Bulger to assume leadership of the Winter Hill Gang. A fellow FBI informant, Stephen Flemmi, became his top lieutenant. Establishing a racket by which he extorted money from bookmakers, loan sharks, drug dealers, and other local criminals, Bulger soon acquired a fearsome reputation both within and beyond the illicit underworld.

Over time Bulger’s corrupt relationship with his FBI contact, Connolly, and the FBI office deepened. Connolly frequently alerted Bulger to other authorities’ investigations into the Winter Hill Gang’s operations and cast a blind eye even to the murders that the organization perpetrated. By the early 1990s the compromised integrity of the FBI with respect to Bulger had become apparent to local and state police, who, along with the federal Drug Enforcement Administration, then launched a new investigation. In January 1995 Bulger, Flemmi, and several others were formally charged with multiple counts of racketeering and extortion. Tipped off by Connolly in advance of the indictment, however, Bulger fled the area. (Connolly was later convicted of several crimes.) By that time local media coverage of Bulger’s misdeeds had become extensive.

After moving from place to place, Bulger and his girlfriend, Catherine Greig, eventually settled in Santa Monica, California, and lived under the assumed identities of Charlie and Carol Gasko. In mid-June 2011 the FBI, which had listed Bulger as one of its 10 most-wanted fugitives since 1999, initiated a public campaign to find Greig. Days later both were apprehended at their home. Although Bulger’s 1995 indictment was subsequently dismissed, he faced an additional indictment that charged him in connection with 19 murders. Two weeks after his arrest, he pleaded not guilty to the charges. In 2012, while Bulger awaited trial, Greig was sentenced to eight years in prison for her role in helping him elude authorities. After a two-month trial in 2013, Bulger was found guilty on 31 criminal counts, which included participation in 11 murders. He was given two consecutive life sentences plus five years.

Bulger spent time in several prisons before being transferred to U.S. Penitentiary Hazelton in northern West Virginia on October 29, 2018. The following day he was killed by several inmates.

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Numerous books were written about Bulger. He was the inspiration for the character of Frank Costello (played by Jack Nicholson) in Martin Scorsese’s film The Departed (2006), and Johnny Depp portrayed him in the biopic Black Mass (2015). His exploits were also chronicled in multiple television shows and documentaries, including Whitey: United States of America v. James J. Bulger (2014), which proved controversial for featuring Bulger’s claim that he was never an informant despite a wealth of evidence otherwise.