1929 – Bulger was born in Dorchester, Massachusetts on the 3rd of September.
1943 – James Bulger was first arrested, at the age of 14, for larceny. He then went on to be arrested for assault and battery and armed robbery. At this time he was associated with a juvenile street gang known as "The Shamrocks".
1948 – Bulger joined the United States Air Force. After completing basic training, he was stationed at the Smoky Hill Air Force Base in Salina, Kansas and later in Idaho.
1950 – He was arrested for going AWOL.
1952 – On the 16th of August, he received an honorable discharge and returned to Massachusetts.
– After returning to Boston, Bulger wasted no time in returning to his old activities. He was involved in the highjacking of a liquor truck.
1955 – He had joined a crew which robbed a string of banks in Rhode Island and Indiana.
1956 – In January, a Federal warrant was issued for his arrest. Bulger then went on the run and was finally arrested in March and sentenced to a lengthy prison term in June.
1973 – Bulger was in control of the rackets in South Boston. Special Agent Condon, Bulger’s contact in the FBI, noted in his log, in September, that Bulger had been heavily shaking down the bookmakers in the area.
– He began to use his influence to remove opposition by persuading Howie Winter to sanction the killings of those whom he viewed as having "stepped out of line."
1979 – Howie Winter and most of his organization’s leadership were sentenced for fixing horse races, the FBI persuaded Federal prosecutors to drop all charges against Bulger and Flemmi.
1988 – Bulger headed an organization that ran all of the rackets (e.g., extortion, loansharking, bookmaking, truck hijackings and arms trafficking) not just in Boston but throughout New England.
– James J. Bulger is currently on the FBI Ten Most Wanted list and a reward for US $1 million is being offered for information leading to his capture.