James "Whitey" Bulger life of crime started at the age of 14 and he’d become a prominent figure in Boston's organized crime scene by the late 1970s. From 1975 to 1990, Bulger also served as an FBI informant, tipping off the FBI and helping bring down Gennaro Angiulo and the Patriarca crime family while building his own crime network and using his status as Protected by the FBI to corner the gap left by Angiulo.
Whitey Bulger was born James Joseph Bulger Jr. on September 3, 1929, in Dorchester, Massachusetts. One of six children born to Roman Catholic Irish-American parents, Whitey gained the nickname due to his white-blond hair; he grew up in a South Boston public housing project known as “Southie”. His father worked as a longshoreman. Bulger was a troublemaker as a child, and even lived out the childhood fantasy of running away with the circus when he was 10 years old. After returning to Boston, Bulger embarked upon a life of crime. His offenses grew increasingly large in scale, culminating in a string of bank robberies from Rhode Island to Indiana. In June 1956, he was sentenced to 25 years in federal prison. He ended up serving 9 years, including stints in Atlanta, Alcatraz, and Leavenworth. He returned to Boston to resume his life of crime. On his release Bulger became an enforcer for crime boss Donald Killeen. After Killeen was gunned down in 1972, Bulger joined the Winter Hill Gang, where he quickly rose up in the ranks as a shrewd and ruthless mobster. Bulger sanctioned and committed numerous killings including the murders of Spike O'Toole, Paulie McGonagle, Eddie Connors, Tommy King and Buddy Leonard. By 1979, Whitey Bulger had become a preeminent figure in Boston's organized crime scene. That year, Howie Winter, the boss of the Winter Hill Gang, was sent to prison for fixing horse races, and Bulger assumed the gang's leadership. Over the next 16 years, he came to control a significant portion of Boston's drug dealing, bookmaking, and loan sharking operations. 1973 Whitey’s life suffered a tragedy that he carried with him the rest of his life when his only child Douglas died at the age of 6 years old after developing “Reyes Syndrome” after an allergic reaction to an aspirin injection, Douglas was his son from a 12 year relationship with Lindsey Cyr. Some say that this was the catalyst for Bulger’s anger and evil streak.
During this same time (from 1975 to 1990), unbeknownst to even his closest associates, Bulger was an FBI informant taking advantage of a family friend special agent John Connelly’s position feeding him with information about the Patriarcas empire, Bulger was also able to take advantage of his brother William's stature in the Massachusetts State Senate, Bulger helped bring down the Patriarcas while simultaneously building a more powerful empire and arguably more violent crime network of his own and in the process making Bulger a cold blooded killer.
James "WHITEY" Bulger
In the spring of 1994, the Drug Enforcement Administration, the Massachusetts State Police and the Boston Police Department launched an investigation into Bulger's gambling operations. In early 1995, Bulger and his associate, Stephen Flemmi, were indicted. Bulger, however, managed to slip through the authorities grasp. According to federal sources it was Bulger's FBI handler and longtime friend Special Agent John Connelly who is believed to be who tipped Bulger off to the 1995 indictment, allowing the criminal to flee with his common law wife, Theresa Stanley but Bulger returned a month later, after Stanley decided that she wanted to return to her children, but fled again soon after with a mistress, Catherine Greig. In 1999, Bulger was officially named on the FBI's "Ten Most Wanted Fugitives" list, at one point being designated the bureau's second most-wanted man, behind only Osama bin Laden. A $1 million reward was issued for providing any information leading directly to his arrest.
After fleeing the Boston area in 1995, Bulger landed on the FBI's "Ten Most Wanted Fugitives" list. He was captured in California in 2011 and faced numerous charges, including participating in 19 murders, money laundering, extortion and drug dealing. Bulger's life on the run ended in June 2011, when he was caught and arrested in Santa Monica, California, after a 16-year manhunt. A tipster had notified the FBI that the 81-year-old fugitive and Greig had been living in a rent-controlled apartment as retirees. The FBI had the building manager lure Bulger to the garage of the apartment by telling him the lock on his storage locker was broken. In the garage, Bulger was surrounded by FBI agents and Los Angeles police officers. He initially insisted he was his alias Charlie Gasko, according to FBI special agent Scott Garriola, until he eventually admitted: “You know who I am; I’m Whitey Bulger.”
Law enforcement officers found 30 guns and more than $822,000 in cash, knives, and ammunition, much of which was hidden in the walls. Greig was also captured and, in March 2012, she pleaded guilty to conspiracy to harbour a fugitive, conspiracy to commit identity fraud, and identity fraud. In June 2012, she was sentenced to 8 years in prison. Jury selection in Bulger's trial began in early June 2013 where he was faced with 33 a count indictment that included money laundering, extortion, drug dealing, corrupting FBI and other law enforcement officials and participating in 19 murders. On August 12, 2013, after a two-month trial, a jury of eight men and four women deliberated for five days and found Bulger guilty on 31 counts, including federal racketeering, extortion, conspiracy and 11 of the 19 murders. They found he was not guilty of 7 murders and could not reach a verdict on one murder. Bulger was sentenced to two life sentences plus five years in prison on November 13, 2013 where he will spend the rest of his life behind bars.
Bulger’s life has been made into a Movie starring Johnny Depp called “Black Mass” but this has been condemned by Bulger’s former hit man Kevin Weeks as being inaccurate in all aspects apart from Depp’s hairline in the movie! Jack Nicholson’s character in Martin Scorseses “The Departed” is also loosely based on Whitey.