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James (Whitey) Bulger, the subject of the new Johny Depp vehicle Black Mass (2015), is one of Boston’s most notorious criminals. Active from the 1970s until the mid 1990s, Bulger was finally captured and convicted of racketeering, extortion, conspiracy, and 11 murders. Now 85 years old, he’s serving two life sentences in high security United States Penitentiary, Coleman II in Florida.

A criminal since his mid-teens, Bulger grew up in a Boston housing project with his five siblings. His criminal determination started early, with his first arrest taking place at age 14. Larceny, forgery, assault and battery, and armed robbery were among his teenage crimes, which landed him five years in a juvenile reformatory. Upon release, he went to the Air Force and ended up in military jail for assault before being arrested for going AWOL.

Through the 1940s and ‘50s, Bulger participated in a number of bank robberies along the east coast, which eventually led to an 1956 arrest and sentencing of 25 years in federal prison. He served nine of those years (between Alcatraz, Atlanta and Leavenworth), then returned to Boston where he achieved the notoriety he is remembered for today.

“Bulger became an enforcer for crime boss Donald Killeen. After Killeen was gunned down in 1972, Bulger was consolidated into the Winter Hill Gang, where he quickly rose through the ranks. A shrewd, ruthless, cunning mobster, Bulger sanctioned numerous killings, including Spike O’Toole, Paulie McGonagle, Eddie Connors, Tommy King and Buddy Leonard.” - Biography.com

By 1979, Bulger was one of the top faces in Boston’s organized crime scene. Drug dealing, bookmaking, and loan sharking became his primary endeavors, and murders piled up under his organization. One of the key factors that allowed Bulger to continue his criminal enterprises was the fact that for nearly 15 years, from 1975 to 1990, he was secretly an FBI informant.

Bulger’s brother, William Bulger, was a Massachusetts Senator from 1978-996 (and eventually went on to become President of the University of Massachusetts from 1996-2003 until a forced resignation). Though William denies having knowledge of Whitey’s actions during his chief criminal years, and has maintained distance from his brother in the years since, Whitey capitalized on his brother’s stature in the senate and various childhood friendships that associated him with Boston’s police force to remain a successful informant.

Bulger’s FBI informacy helped topple the Patriarcas, a New England crime family, and boosted Bulger’s own criminal organization. The way Bulger kept quiet about being an FBI informant was very successful, as even his closest associates were unaware of the arrangement that lasted a decade and a half.

Eventually indicted for his crimes, Bulger fled Boston and evaded capture, making his way to the FBI’s “Most Wanted’ list until being discovered in 2011 in Santa Monica, California with a mistress, some 16 years after being on the run. He had been tipped off about the indictment by a former FBI handler who revealed the FBI was going to use President Nixon’s RICO act to bring him in - a federal law which allows organized crime leaders to be responsible for crimes ordered under their authority, whether they performed them or not.

“James “Whitey” Bulger showed no mercy to the people he tortured and killed. He refused to get on his knees when captured after more than a decade on the run because he didn’t want to get his pants dirty. And he swore at witnesses during his trial.” - Boston Globe