1953: Bulger, then 24, moves on from gang fights of his youth and becomes a career criminal, progressing from hijacking to bank holdups.
1956: Bulger, hiding out and his hair dyed black, is hauled out of a Revere nightclub on charges of robbing banks in Melrose, Providence, and Indiana. He is convicted and serves nine years in federal penitentiaries, including Alcatraz, before returning to Boston in 1965.
1979: The incarceration of Winter Hill Gang leader Howie Winter leaves Whitey Bulger and his right-hand man, Stevie Flemmi, in control of all non-Mafia rackets in Greater Boston. Bulger had joined the gang shortly after getting out of prison for bank robbery in 1965.
1980: State Police bug North Station garage where Bulger holds court and collects tribute from bookmakers. Apparently knowing they are being listened to, Bulger and his associates engage in idle, sometimes sarcastic banter. No arrests follow and the seeds of law enforcement mistrust are planted.
1981: FBI bugs the North End headquarters of the Angiulo brothers, gathering the evidence that will ultimately destroy the Angiulos’ four-decade reign as premier organized crime group in metropolitan Boston. They are arrested in 1983.
1983: State trooper notices bookies showing up at Heller’s, a nondescript Chelsea bar, which turns out to be the bookies’ “bank,” where checks from gamblers are laundered. FBI joins case, plants bugs in 1986, and authorities learn who pays “rent” to the Mafia and who pays to Winter Hill. It becomes the key to bringing the Bulger case.
1986: FBI bugs Vanessa’s, an Italian food emporium in the Prudential Center, where the successors to the Angiulo regime have set up shop. The Mafiosi who gathered there to shake down bookies are indicted in 1989 and imprisoned in 1990.
1989: Mafia boss Frank Salemme survives assassination bid by rivals from Vanessa’s. A South Boston bar owner and mortgage company official, Tim Connolly, claims Whitey Bulger menaced him with a knife, demanding $50,000 after Connolly dropped tha ball on getting a loan for a drug trafficker who owed Bulger money - the strongest evidence yet linking Bulger to drugs and violence.
1990: 51 people said to be part of a South Boston-based drug ring overseen by Bulger’s underlings are arrested. All eventually plead guilty, but only one of them agrees to cooperate with government, and he does not implicate Bulger.
1991: State Police convince bookie Burton (Chico) Krantz agrees to become an informant. He claims he paid “rent” to Bulger and Flemmi. State Police bring evidence to federal authorities, and joint investigation goes on for more than three years.
1995: Fearing some of the suspects may be preparing to flee, state and federal agents swoop in. Flemmi is captured as he leaves a Financial District restaurant. Bulger and Salemme get away. Indictment charging them and four others, mostly with extorting bookies, is unsealed. For the first time in 39 years, Whitey Bulger is facing criminal charges.