Timeline: Whitey Bulger's Life In Boston

By WGBH News

June 22, 2011

'Whitey' Bulger, in 1984 file photos originally released by the FBI. (AP Photo/FBI)

September 3, 1929: James Bulger is born to Irish immigrant parents living in Boston's Dorchester neighborhood. He is the second of six children. His shock of platinum blonde hair earns him the nickname "Whitey."

1956: Whitey Bulger is sentenced to federal prison for bank robbery. Suspected of plotting an escape from prison in Atlanta, he's transferred to Alcatraz.

1960: Bulger's younger brother, William, is elected to the state House of Representatives. John Connolly, a childhood friend from South Boston who would become an FBI agent in the 1970s, works on the campaign.

The Mary Ellen McCormack housing development in South Boston, formerly the Old Harbor Housing project, where Bulger grew up. (AP Photo/Steven Senne)

1965: Whitey Bulger is released from prison and comes home to live with his mother at the Old Harbor housing project in Southie. He works as a custodian at Suffolk County Courthouse. But within a year he is hanging around Marshall Motors in Somerville, a sort of headquarters for the Winter Hill Gang, and soon becomes a top lieutenant to its boss, Howie Winter.

As a result of his imprisonment for half of the decade, Whitey missed some of the worst violence of the Irish gang wars going on around Boston. But he soon became a much-feared member of the Killeen gang, and was  likely involved in a number of South Boston murders in the late 1960s and early 70s.

“From gangsters to God”: story from the Somerville News about the run-down Marshall Street garage being turned into a Pentecostal church.

From WGBH's "Greater Boston": A story about Lindsey Cyr of Weymouth, who says she and Bulger had a child together in 1967. Cyr says she gave birth to Bulger’s only known child, Douglas Glenn Cyr, in, 1967. Douglas died of Reye’s Syndrome, a severe reaction to aspirin, in 1973.

Mid-1960s: Gangster Stephen "The Rifleman" Flemmi, an Italian from Roxbury, develops a relationship with FBI agent H. Paul Rico. Flemmi, using the code name "Jack from South Boston" informs on members of the Providence-based New England Mafia. One of Flemmi’s brothers is a Boston police officer.

1970: William Bulger is elected to the state Senate.

FBI Agent John Connolly, entering Federal court in Boston for his trial in 2002. (AP Photo/Olivia Gatti)

1970s: The highly contentious desgregation busing plans in South Boston help Bulger consolidate his influence there. He prevents his gang from getting involved in the protests, which he expects would attract more police and federal attention, and tries to tone down the outrage in the neighborhood.

The same is true for William Bulger: although not wanting to appear racist to statewide voters, he stands up for his constituents and forcefully opposes busing plans. In doing so, he cements his position in Dorchester and South Boston politics, while trying to stop the unrest from escalating.

September 1975: Acting partly on Flemmi's recommendation, Bulger cuts a deal with Connolly to provide information on the Italian Mafia in exchange for protection from the FBI.

1978: William Bulger becomes president of the state Senate and goes on to serve in the post longer than anyone in its history.

Suffolk County Courthouse
The John Adams Courthouse, Suffolk County & Supreme Judicial Court. (hyperion327/Flickr)

At this time, John E. Powers, himself a former Senate president, is clerk of the Supreme Judicial Court at Suffolk County Courthouse. He finds that Whitey Bulger is still on the Courthouse payroll, though he had left his job there in 1971.

Powers, apparently resentful of the younger Bulger's fast rise to the presidency, cuts Whitey's salary. William Bulger retaliates four years later by having any increase in pay for Powers’ job frozen.

June 1978: Four known gangsters and a former Boston Channel 7 investigative reporter and anchorman, John A. Kelly, are killed by unknown shooters at the Blackfriars Pub in downtown Boston. Kelly had for some time been building relationships in the local underworld — probably initially to pursue a story, but he soon got in over his head.

By this time, Kelly had been fired from his job for other reasons and was managing Blackfriars, where he had hired Flemmi’s mistress, Marilyn DiSilva, as a waitress. Drugs and guns found at the bar, combined with the known victims who had associations with the Winter Hill Gang, have suggested that Bulger and Flemmi were involved.

“Dangerous liaison”: In the Boston Globe Magazine, DiSilva talks about hanging around the Marshall Street garage in those days, and all the violence from which she was just a step or two removed. She says Flemmi told her not to go in to work the night of the massacre.

1979: After a former business associate implicates Bulger and Flemmi in a horse race-fixing scheme, FBI agents Connolly and his supervisor, John Morris, persuade federal prosecutors to leave the two out of the indictment. Twenty-one people are charged, including Howie Winter, whose conviction paves the way for Bulger and Flemmi to assume control of the Winter Hill Gang.

Late 1970s, Early 1980s: Cocaine and crack cocaine hit American streets and Bulger gets involved. Southie folklore has long held that Bulger kept drugs out of the neighborhood. But as this story from the Globe shows, quite the opposite was true: Bulger charged massive amounts of money from drug dealers in exchange for operation in the areas he controlled.

1981: Flemmi allegedly strangles Bulger's girlfriend, Debra Davis, because she is seen as a threat to reveal what she knows to law enforcement. Her family later files suit against the federal government for protecting Bulger as an FBI informant.

January 1995: Bulger disappears on the eve of his indictment on racketeering charges.

1997: The FBI, under court order, acknowledges that Bulger and Flemmi were "top echelon" informants, as a federal probe into the agency's corrupt ties to its mob informants begins.

A site in Quincy where an unidentified body, thought to be a Bulger victim, was found in 2000. (AP Photo/Angela Rowlings)

2000: Testimony by Bulger’s friend and associate Kevin Weeks leads to the discovery of five bodies, spread around Dorchester and Quincy. Some were rivals of Bulger, some were personal acquaintances or girlfriends, not involved in criminal activities. Debra Davis was among those found.

May 2002: Connolly is convicted of racketeering for warning Bulger, Salemme and Flemmi that they were about to be indicted in January 1995.

From WGBH's “Greater Boston”: This 2001 episode tells the story of Bulger and Agent Connolly, recorded before his trial.

June 2003: William Bulger testifies before a congressional committee investigating the FBI's ties to mobster informants such as his brother. After receiving immunity, he acknowledges receiving a call from Whitey shortly after he fled, but says he has not heard from him since and has no idea where he is. Amid growing pressure, he resigns as president of the University of Massachusetts system shortly thereafter.

2005-2010: During this time, Bulger and his girlfriend, Catherine Greig, are spotted in London. Then they are thought to have been caught on tape in a small Italian town, but those people are later identified as a tourist couple from Germany.

2008: Connolly is convicted of second-degree murder in relation to the 1982 killing of a former henchman by Bulger and Flemmi, as prosecutors argue he provided critical information to the mobsters. He also produced an FBI report on the murder at the time that implicated rival gangsters in place of Bulger and Flemmi.

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