Who was James 'Whitey' Bulger?

PHOTO: James "Whitey" Bulger is seen in this undated police photo.PlayU.S. Marshals Service/AP
WATCH Notorious Boston mob boss found dead in jail cell

One of the most notorious crime bosses in the country, the powerful "Whitey" Bulger was killed in prison on Monday - the details are still unknown, but what is known is how Bulger lived his 89 year life.

James "Whitey" Bulger was born in South Boston- and developed a street sense early on, joining a gang and getting arrested, as well as spending time in jail - a pattern for Bulger throughout his life.

PHOTO: James Whitey Bulger is seen in this undated police photo. U.S. Marshals Service/AP
James "Whitey" Bulger is seen in this undated police photo.

After two stints behind bars, Bulger returned to south Boston where he worked as a janitor and construction worker and then eventually a bookmaker and loan shark under the infamous Donald Killeen, who ran the South Boston streets for over 20 years.

PHOTO: James Whitey Bulger holds John Martoranos youngest son, John Jr., during his Christening ceremony in this undated handout photo provided by the U.S. Attorneys Office of Massachusetts, June 18, 2013. U.S. Attorneys Office of Massachusetts/Reuters
James "Whitey" Bulger holds John Martorano's youngest son, John Jr., during his Christening ceremony in this undated handout photo provided by the U.S. Attorney's Office of Massachusetts, June 18, 2013.

Killeen was eventually murdered and Bulger joined Howie Winter's Winter Hill Gang - and started shaking down local bookies in the area.

In 1974 - Bulger for the second time was approached by the FBI to be an informant and this time accepted at the behest of John Connolly, a childhood friend and FBI Special Agent.

PHOTO: Former FBI agent John Connolly and wife Liz arrivie for trial at Moakley Courthouse in Boston, May 22, 2014. George Rizer/The Boston Globe via Getty Images
Former FBI agent John Connolly and wife Liz arrivie for trial at Moakley Courthouse in Boston, May 22, 2014.

From then on Bulger had a man inside the federal government. A source of frustration for the Massachusetts State Police who were vigorously investigating the mobster.

Bulger, while an FBI informant, was "operating without any restrictions," according to Tom Foley a retired Col. in the Mass State Police told ABC News.

PHOTO: James Whitey Bulger is pictured in this undated photo provided to the court as evidence by Bulgers defence team on July 31, 2013 and released to the media by the the U.S. Attorneys Office in Massachusetts. U.S. Attorneys Office of Massachusetts/Reuters
James "Whitey" Bulger is pictured in this undated photo provided to the court as evidence by Bulger's defence team on July 31, 2013 and released to the media by the the U.S. Attorney's Office in Massachusetts.

Foley added that the frustration became bigger than Bugler, because the FBI was letting him get away with crimes in an effort to nab members of the Italian organized crime family, or LaCostra Nosa. The FBI has not commented on these allegations.

Bulger's reign lasted until 1995 and he committed various illegal acts while the head of the Winter Hill Gang.

Interestingly enough, Bulger's brother, was the President of the Massachusetts State Senate and President of the University of Massachusetts. During Whitey Bulger's time of reign, Billy Bulger was the President of the State Senate.

PHOTO: William Bulger, brother of Whitey Bulger, leaves the Moakley Federal Courthouse after sitting in the courtroom during the hearing, June 24, 2011. John Tlumacki/The Boston Globe via Getty Images
William Bulger, brother of Whitey Bulger, leaves the Moakley Federal Courthouse after sitting in the courtroom during the hearing, June 24, 2011.

In all, Bulger was proven to have killed 11 people, and while there was suspicion he was involved with another 7 murders, those could not be proven.

After 1995 Bulger went on the run for 15 years as the DEA began zeroing in on his illegal bookmaking operation, according to the Boston Globe.

He was captured in 2011, along with his girlfriend Catherine Greig, and tried in Boston in 2013 where he was convicted on charges including firearms possession and racketeering, which implicated him in 19 murders. Bulger was ultimately sentenced to life in prison.

Col. Foley said upon hearing of the death of Bulger he felt "good, a little bit for the families."

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