Whitey Bulger

Whitey Bulger Biography

Whitey Bulger was a prominent figure in Boston's organized crime scene from the 1970s until the mid-'90s, when he fled the area. Captured in 2011, he was later found guilty of federal racketeering, extortion, conspiracy and 11 murders.

Who Was Whitey Bulger?

James "Whitey" Bulger embarked upon a life of crime at the age of 14 and had 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 police to the Patriarca crime family while also building his own crime network. 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 after a two-month trial, the notorious crime boss was found guilty of federal racketeering, extortion, conspiracy and 11 murders.

Whitey Bulger in Alcatraz Prison Photo

Whitey Bulger's mug shot in Alcatraz. 

Whitey Bulger Movie Depictions

Of the various movies and documentaries that were made about or inspired by Bulger, Martin Scorsese's character Frank Costello, (played by Jack Nicholson), in The Departed (2006) was loosely based on Bulger's life of crime. 

In 2015 Johnny Depp played the criminal in the biopic, Black Mass, also starring Joel Edgerton as FBI agent John Connolly and Benedict Cumberbatch as William Bulger. 

Whitey Bulger's Brother

While Whitey was a distinguished criminal boss in the Boston mob, his younger brother, William Michael "Billy" Bulger (born 1934), built a distinguished career in politics, becoming the longest-running president of the Massachusetts senate. He was also president of the University of Massachusetts but was forced to resign in 2003 for refusing to answer questions about his fugitive brother in a congressional hearing.

Secret Son

Before Bulger ran off as a fugitive with his various mistresses, he was involved with former fashion model and waitress Lindsey Cyr, who eventually became his common law wife in the 1960s. They had one son, Douglas Glen Cyr (born 1967), but the boy died at age six from Reye's Syndrome, after experiencing a severe allergic reaction to aspirin. When Douglas died, Cyr claimed that Bulger was devastated.

Bulger's Net Worth

Throughout his criminal career, Bulger amassed $25 million, according to federal court files.  

Early Life



Life of Crime: Doing Time in Alcatraz

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 nine years, including stints in Atlanta, Alcatraz and Leavenworth. (Bulger allegedly served time in Alcatraz because he was discovered making plans to escape from his prison in Atlanta.)

Looking back fondly at his three-year stay in Alcatraz, Bulger admitted to CNN (after his 2011 capture) that "'If I could choose my epitaph on my tombstone, it would be 'I'd rather be in Alcatraz.' '" 

Regardless, after he did his time, Bulger returned to Boston to resume his life of crime. He 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. A shrewd, ruthless, cunning mobster, Bulger sanctioned numerous killings, including the murders of Spike O'Toole, Paulie McGonagle, Eddie Connors, Tommy King and Buddy Leonard.

Becoming Boss of the Winter Hill Gang

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 loansharking operations. 


Fugitive Life With Mistresses Theresa Stanley, Catherine Greig

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, Bulger's FBI handler, longtime friend Special Agent John Connelly, tipped Bulger off to the 1995 indictment, allowing the criminal to flee with his girlfriend, Theresa Stanley.

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.

Capture and Trial


Inside the apartment, law enforcement found 30 guns, 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 harbor a fugitive, conspiracy to commit identity fraud and identity fraud. In June 2012, she was sentenced to 8 years in prison.


Whitey Bulger Found Guilty


Bulger was sentenced to two life sentences plus five years in prison on November 13, 2013. According to the Chicago Tribune, U.S. District Judge Denise Casper told Bulger that "The scope, the callousness, the depravity of your crimes are almost unfathomable," during his sentencing hearing.



On October 30, 2018 at around 8:20 am, Bulger was found unresponsive at a United States Penitentiary in Hazleton, West Virginia, where he was recently transferred.

Fact Check
