Who is Whitey Bulger?

If you have not yet watched the documentary “Whitey: United States of America v. James J. Bulger” then you are missing out. The documentary examines the 2013 trial of the notorious Whitey Bulger, and uncovers the disturbing issue of massive corruption within the Boston Police Department and FBI surrounding Bulger at the time.

Who is Whitey Bulger?

James “Whitey” Bulger was topped only by Osama Bin Laden on the FBI’s Most Wanted list, as a result of his actions as the boss of an Irish mafia family called Winter Hill, which terrorized the citizens in and around Boston for years. He was finally arrested in California in 2011, at age 81. At the time of arrest, he was charged with 19 murders. He was arrested hiding in plain sight with his longtime girlfriend in an apartment complex in Santa Monica. This begs the question of how hard the FBI was actually looking for Whitey Bulger.

Why Did it Take So Long to Find Him?

According to legend, and discussed in the documentary, Whitey Bulger was actually an FBI informant from 1975 until the time of his disappearance. He provided the FBI with information about the Patriarca crime family, a rival Italian mob family, in exchange for protection from being punished for his own crimes. This arrangement worked until 1994, when an FBI agent actually tipped Bulger off to his pending indictment. He and his girlfriend fled in the middle of the night, not to be seen again for 17 years in an apartment complex in Santa Monica.

Did the FBI Help Bulger?

Whitey Bulger was finally brought to trial in federal court in Boston in 2013, where former allies of his Winter Hill Gang testified against him. Court records indicate that his massive criminal racketeering enterprise was built with the assistance of many corrupt officials inside the Department of Justice and the FBI.

Agent Connolly is the FBI agent in charge of managing Whitey Bulger during the time he acted as an informant. Whitey Bulger claims he never provided information about an Italian crime family to FBI agent Connolly. During his trial, his lawyers tried to prove that Agent Connolly and the FBI falsified this claim and information related to this claim to make Whitey appear to be a valuable asset and thereby protect him from the authorities. Bulger maintained throughout his trial that he was the one calling the shots in the relationship, not Agent Connolly. Connolly was later found to have falsified records, as Bulger indicated.

Connolly and his supervisor were arrested and charged as well. As a result, Connelly is serving a 40 year sentence in a Florida prison as a result of his involvement in a hit put out by the Winter Hill Gang on a John Callahan. Connolly’s supervisor, Morris, admitted to the corruption of himself and others in exchange for immunity. The FBI at that time had very deep ties with many unsavory informants, including one of the Winter Hill Gang’s criminal lieutenants, Stephen “The Rifleman” Flemmi. Flemmi had been secretly cooperating with the FBI and bribing Connolly and Morris with trips, wine, and cash. This bribery went on from 1975 until Flemmi was arrested in 1995.

The Trial

In June 2013, Bulger was finally charged with 32 counts of racketeering. He was also charged with money laundering, extortion, weapons charges, and nineteen (19) murders. He was ultimately found guilty on 31 criminal charges, including 11 of the murder charges, and in November 2013 was sentenced to two life terms in prison and five years.

Some of the More Sensational Charges against Bulger

Flemmi (The Rifleman) testified in Bulger’s trial about much criminal activity, including the time Bulger murdered his stepdaughter. According to Flemmi, he brought his stepdaughter, who was alleged to be a drug-addicted prostitute, to a South Boston brownstone where she was murdered by Bulger (strangled with his bare hands, according to trial testimony). After Bulger killed her, he allegedly told Flemmi to “clean up your mess” and Flemmi proceeding to pull the teeth from his own stepdaughter’s mouth so the authorities would not be able to identify her remains. Apparently this was common practice for the Winter Hill Gang after killing somebody.

When and Why Did Bulger Turn to a Life of Crime?

While not readily clear why anybody embraces a criminal lifestyle outside of necessity, Bulger was first arrested at age 14 for theft. His criminal record escalated from there, and while still a juvenile, he was arrested for forgery, larceny, assault and battery, and ultimately armed robbery, for which he served only five years in a juvenile facility. He even served time in a military prison after he joined the Air Force, for going AWOL. He somehow received an honorable discharge in 1952, and became an increasingly emboldened criminal. He was ultimately sentenced to 25 years in federal prison in June 1956 for bank robbery, although he served only nine years before returning to Boston and becoming an enforcer for crime boss Donald Killeen, who was later gunned down. In 1972, Bulger joined the Winter Hill Gang, and rose through the ranks, basically killing anyone in his path.

By 1979, Bulger was the preeminent figure in the organized crime scene in Boston, and when Howie Winter, the boss of the Winter Hill Gang, went to prison, Bulger ascended to gang leader. For the next 16 years, Bulger controlled a large portion of all the bookmaking, loan-sharking, and drug dealing that went on in Boston. He was able to take advantage of his brother William’s status as a Massachusetts State Senator to link himself to law enforcement, and used those ties to secretly inform on his enemies and strengthen his hold even further on the Boston crime scene.


Whitey Bulger was a criminal mastermind, in some ways. He used law enforcement to eliminate his enemies, and was able to remain a fugitive for fifteen years. He is a unique and powerful crime figure in American criminal history and mob history, and there will likely be many more movies made about his power and reach.

At Ozols Law Firm we handle all types of criminal cases, not just crime boss cases. We are standing by waiting to fight for your freedom.