Offences & Incarceration
His criminal life started at the age of 14 when he was arrested for delinquency. He became a part of the street gang ‘Shamrocks’ and was sent to a juvenile reformatory for five years, on charges of larceny, assault and battery.
Upon his release in 1948, he joined the US Air Force and served in Kansas and Idaho. However, when he revealed his true colors, he was arrested in 1950 for going absent without leave, but was discharged honorably in 1952.
He returned to Massachusetts, where his criminal offences increased, starting with his arrest in 1956 for bank robbery. He was jailed for 25 years in federal prison, but was released in 1965.
He came back to South Boston and became an enforcer for gangster Donald Killeen. After Killeen’s murder in 1972, he joined Winter Hill Gang where he transformed into a shrewd, ruthless mobster.
He carried out various murders, killing members of the rival Mullen gang, including Paulie McGonagle, Tommy King, and Spike O’Toole, apart from shooting Buddy Leonard and Edward Connors.
He served as an FBI informant during 1975-90 for providing information linked with Italian mafia, thereby utilizing this power to eliminate his associates who supposedly posed a threat to him.
His brother, William Bulger, became the President of the State Senate in 1978, which he took to his advantage in several of his murder carry-outs.
In 1979, Howie Winter’s arrest for horse race-fixing paved way for him and his partner Stephen Flemmi, to take over the Winter Hill Gang as the leader, thereby increasing drug dealing, loan sharking and bookmaking at large.
He, along with Flemmi and Weeks, carried out extortion, bookmaking, trafficking, truck hijacking and loan sharking openly during the 1980s, due to intense support from FBI agent John Connolly and Lt. Richard J. Schneiderhan.
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In May 1981, he and Flemmi organized the killing of Roger Wheeler, in a money skimming case. Wheeler was shot by John Martorano, a hit-man in the Winter Hill Gang.
He ordered Martorano to murder John Callahan, former president of World Jai Alai, so that he would not help investigators in the Jai Alai scheme.
He helped the FBI end his top rival Italian-American Patriarca crime family, with the arrest of underboss Gennaro Angiulo in 1986, after which he took over the crime network in the Boston area.
In December 1994, he left Boston, with Theresa Stanley, after Drug Enforcement Administration, Massachusetts State Police and Boston Police Department started searching for him.
He changed his plan of returning to Boston in January 1995 after learning about Flemmi’s arrest by his police detective brother, Michael Flemmi.
After moving across cities for three weeks, he met Kelvin Weeks in Dorchester, from where he fled with a mistress, Catherine Elizabeth Greig.
He and Greig were arrested on June 22, 2011 in Santa Monica, California, after a Bulger Fugitive Task Force was formed to nab him, thereby ending his underworld reign.
He was put on trial and on July 6, 2011 found guilty on 48 charges, including 19 murders, perjury, extortion, narcotics distribution, money laundering, weapons violation and others.
On June 12, 2012, Greig confessed using fake identities in concealing Bulger and was sentenced to eight years imprisonment.
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On November 14, 2013, he was charged on 31 counts, including 11 murders, and sentenced to two life terms plus five years imprisonment. He is currently incarcerated in the United States Penitentiary Coleman II, Sumterville, Florida.
Personal Life & Legacy
He met waitress and fashion model from North Weymouth, Massachusetts, Lindsey Cyr in 1966, after which the two shared a live-in relationship with a common law marriage for 12 years.
The couple had a son – Douglas Glenn Cyr, in 1967. However, he suffered from Reye’s Syndrome, an allergic reaction to an aspirin injection, and died in 1973 at the age of six.
After Bulger and Cyr ended their relationship, he got involved with Theresa Stanley, a divorcee with several kids from South Boston.
The ‘Brotherhood’ series, broadcast on Showtime channel during 2006-08, was inspired by the relationship of Whitey and Billy Bulger, standing on opposite sides of the law.
His trials became a subject of the 2014 documentary ‘Whitey: United States of America v. James J. Bulger’, directed by Joe Berlinger.
Director Scott Cooper’s ‘Black Mass’, starring Johnny Depp as Bulger, based on the 2012 book ‘Black Mass’ authored by Dick Lehr and Gerard O’Neill, is due to release in 2015.