1953: Bulger, then 24, moves on from gang fights of his youIth 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 the ball on getting a loan for a drug trafficker who owed Bulger money - the strongest evidence yet linking Bulger to drugs and violence.
1990: Fifty one 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.
1994: Bulger flees with girlfriend Teresa Stanley after he is warned by his former handler, retired FBI agent John J. Connolly Jr., that he’s about to be indicted on federal racketeering charges.
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.
Jan. 11-14, 1995: Bulger drops Stanley off in Hingham and picks up another girlfriend, Catherine Greig.
1996: Bulger and Greig, traveling under aliases, stay in Louisiana, New York, and elsewhere.
1999: Weeks and another longtime Bulger associate, Kevin O’Neil, are indicted on federal racketeering charges. Bulger loses his trusted confidante and primary contact in South Boston as Weeks begins cooperating almost immediately, helping authorities build a murder case against Bulger.
Bulger’s longtime handler, retired FBI agent John J. Connolly Jr., is indicted on federal racketeering charges. He was later convicted of warning Bulger about his indictment and is serving a 10-year prison term.
2000: Greig is spotted at a hair salon in Fountain Valley, Calif., where she had her hair dyed while Bulger waited in a car parked outside.
A new sweeping federal indictment brought in US District Court in Boston charges Bulger with killing 19 people between 1973 and 1985, including murders in Florida and Oklahoma, two states that carry the death penalty. Flemmi is charged with killing nine people and later pleads guilty. He is sentenced to life in prison and is currently cooperating with the government.
2002-2007: Bulger and Greig are allegedly spotted in various places in Europe.
2008: FBI doubles its reward to $2 million for information leading directly to Bulger’s capture. It’s the largest reward offered by the FBI for a domestic fugitive.
2011: A tip leads to the capture of Bulger and Greig at an apartment building in Santa Monica, California.
2012: Greig is sentenced to eight years in prison for helping Bulger evade capture for more than 16 years.
June 12, 2013: Bulger’s trial on murder and racketeering charges opens in Boston. Bulger’s attorney acknowledges his criminal career, but says Bulger was not a federal informant and did not kill anyone.
Aug. 12, 2013: A jury convicts Bulger, then 83, of being involved in 11 murders and several other crimes, including drug trafficking, sending him to prison for the rest of his life. Bulger’s attorney says he intends to appeal, arguing he hould have been allowed to present a claim that a former federal prosecutor promised Bulger immunity.
2016: The US Supreme Court declines to hear Bulger’s appeal. Now 87, Bulger is held at the maximum security federal prison at Sumterville, Fla.
2018: Bulger is moved to a federal transfer facility in Oklahoma City. He’s expected to be transferred to a federal prison medical facility.
Oct. 30, 2018: Bulger is killed at a federal prison in West Virginia. A fellow inmate with Mafia ties was investigated for the slaying. Bulger was 89.