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Black Mass: History vs. Hollywood

Starring Johnny Depp, Benedict Cumberbatch, Dakota Johnson, Joel Edgerton | based on the book "Black Mass: The True Story of an Unholy Alliance Between the FBI and the Irish Mob"

Johnny Depp
Born: June 9, 1963
Owensboro, Kentucky, USA
James "Whitey" Bulger, Jr.
Born: September 3, 1929
Birthplace: South Boston, Massachusetts, USA
Benedict Cumberbatch
Born: July 19, 1976
Hammersmith, London, England, UK
William "Billy" Bulger
Born: February 2, 1934
Birthplace: Dorchester, Massachusetts, USA
Dakota Johnson
Born: October 4, 1989
Austin, Texas, USA
Lyndsey Cyr
Born: February 21, 1945
Birthplace: Massachusetts, USA
Luke Ryan
Douglas Cyr
Born: 1967
Death: 1973 (Reye's Syndrome)
Joel Edgerton
Born: June 23, 1974
Blacktown, New South Wales, Australia
John Connolly
Born: August 1, 1940
Birthplace: Boston, Massachusetts, USA
Adam Scott
Born: April 3, 1973
Santa Cruz, California, USA
Robert Fitzpatrick
Birthplace: New York, USA
Juno Temple
Born: July 21, 1989
London, England, UK
Deborah Hussey
Born: February 14, 1958
Birthplace: Massachusetts, USA
Death: January 1985, South Boston, Boston, Massachusetts, USA (strangled)
Corey Stoll
Born: March 14, 1976
New York City, New York, USA
Fred Wyshak
Born: November 22, 1952
Birthplace: Boston, Massachusetts, USA
Jesse Plemons
Born: April 2, 1988
Dallas, Texas, USA
Kevin Weeks
Born: March 21, 1956
Birthplace: Boston, Massachusetts, USA
Peter Sarsgaard
Born: March 7, 1971
Belleville, Illinois, USA
Brian Halloran
Born: July 23, 1940
Birthplace: Medford, Massachusetts, USA
Death: May 11, 1982, Boston, Massachusetts, USA (gunshot)
Rory Cochrane
Born: February 28, 1972
Syracuse, New York, USA
Stephen "The Rifleman" Flemmi
Born: June 9, 1934
Birthplace: Roxbury, Boston, Massachusetts, USA
David Harbour
Born: April 10, 1974
New York, USA
John Morris
Born: 1947
W. Earl Brown
Born: September 7, 1963
Murray, Kentucky, USA
Johnny Martorano
Born: December 13, 1940
Birthplace: Somerville, Massachusetts, USA
Sienna Miller (cut from movie)
Born: December 28, 1981
New York City, New York, USA
Catherine Greig
Born: April 3, 1951
Birthplace: Boston, Massachusetts, USA
I never, never, never cracked. And the Boston FBI, no way. I met John Connolly who was a salty guy, Irish Catholic like myself. You know, it's friendship, 'Geez, if I ever hear anything I'll tip you off, give you a heads up,' and then I told him, 'Alright, John.' I says, 'I'll see ya, you can let me know. I'd appreciate it.' And that's how it got started. -James "Whitey" Bulger, Mail Online

Questioning the Story:

At what age did Whitey Bulger begin his life of crime?

The real Whitey Bulger started his life of crime as a juvenile and was arrested for theft in 1943 when he was 14, at which point he was already a member of a street gang known as the "Shamrocks" ( As a minor, Whitey was arrested for assault and battery, larceny, forgery, and armed robbery. He spent five years in a juvenile reformatory (

Whitey Bulger's mugshots became less frequent after he developed a relationship with the FBI and Agent John Connolly.

Why was James Bulger nicknamed "Whitey"?

As Bulger's criminal ways escalated as a teen, the police became familiar with him and nicknamed him "Whitey" for his youthful blond hair. -Whitey Bulger: The Making of a Monster

Is Kevin Bacon's character, Charles McGuire, based on a real person?

No, at least not any single person. In researching the Black Mass true story, we learned that the Charles McGuire character is a combination of various agents who were supervisors at the Boston FBI over the years.

Did James "Whitey" Bulger and John Connolly really meet as kids?

Yes. James "Whitey" Bulger is roughly eleven years older than John Connolly. The two met in 1948 at an ice cream shop when Connolly was just eight-years-old. Bulger, then in his late teens, bought ice cream for Connolly and his friends. Connolly would later describe the experience as being "like meeting Ted Williams." Later that same year, Bulger ran off a bully who was trying to pick a fight with Connolly. It is this incident that is referenced in the movie.

Did James "Whitey" Bulger really do time in Alcatraz?

Yes. In 1956 at age 27, Bulger was given a 20-year federal sentence for armed robbery and truck hijacking. He spent the first three years in Atlanta Penitentiary and then following a failed escape plot, he was transferred to Alcatraz Federal Penitentiary in November 1959. He was there for three years before being transferred to Leavenworth in 1962 and then to Lewisburg Federal Penitentiary in 1963. After serving a total of nine years, he was released in 1965 with the help of his brother Billy, a politician who was then a member of the Massachusetts House of Representatives. Several decades later, while Whitey was on the lam with Catherine Greig, he visited Alcatraz, which had been shut down in 1963. The couple took a tour and dressed up in prison garb that was likely all too familiar to Bulger. -Black Mass: Whitey Bulger, the FBI, and a Devil's Deal

While on the lam, former Alcatraz inmate Whitey Bulger and girlfriend Catherine Greig visit the legendary prison decades after it closed.

Was Whitey Bulger really used as a guinea pig in prison for a government sanctioned LSD-testing program?

Yes. The Black Mass true story reveals that while in prison for bank robbery in the late 1950s, Whitey Bulger volunteered to participate in a CIA program named MK-ULTRA in exchange for reduced time on his sentence. The program studied the effects of LSD and other drugs on humans, in this case using inmates as test subjects. In a notebook, Whitey wrote of "horrible LSD experiences followed by thoughts of suicide and deep depression." The CIA had been using MK-ULTRA to research the possible use of LSD as an interrogation agent or an incapacitating agent. -CBS Boston

Did Whitey have a son who died as a boy?

Yes. Like in the Black Mass movie, the real Whitey Bulger had a son, Douglas Cyr, who died at age six from Reye's Syndrome (a severe reaction to aspirin). The boy's mother, Lindsey Cyr (portrayed by Dakota Johnson in the movie), said that Douglas's death had a definite impact on Whitey, who had been an attentive and caring father. "He changed after Douglas died," Lindsey said. "He was colder." The movie certainly conveys this.

Did Whitey Bulger really threaten John Connolly's wife?

No, we found no evidence that Bulger threatened Marianne Connolly by putting his hand around her neck. In real life, John and Marianne Connolly separated in 1978, with Marianne eventually filing for divorce in January 1982. The movie keeps Marianne in the picture longer. However, the reason that the marriage broke down seems to be accurately depicted in the movie. Connolly's manner and style began to change as he became more like a gangster than an FBI agent. -Black Mass: Whitey Bulger, the FBI, and a Devil's Deal

How many people did Whitey Bulger kill?

James "Whitey" Bulger was indicted for 19 murders. As stated in the movie, he was found guilty for 11 of those murders. He was acquitted of seven (the jury was unable to reach a conclusion on an eighth). However, fellow Winter Hill Gang member Kevin Weeks says that Bulger claimed to have killed 37 people.

On November 14, 2013, after being found guilty on 31 counts, he was given two back-to-back life sentences plus five years. In addition, he was ordered to pay close to $20 million in restitution.

Whitey was found guilty in 11 of the 19 murders for which he was indicted.

Did Whitey Bulger's supposed role as an FBI informant result in anything positive?

Yes. Bulger's alleged role as an FBI informant helped to bring down the Patriarcas, a crime family in New England. However, by taking out a rival gang family, the FBI essentially helped Bulger build a more powerful and deadly crime syndicate of his own.

To what extent was Whitey Bulger an FBI informant?

To this day, the real Whitey Bulger emphatically claims that he was never an informant. "I never, never, never cracked," said Whitey (Mail Online). During his trial, Bulger's defense attempted to prove that he was never a snitch and others testified that it was instead the corrupt FBI agents who were in his pocket. A federal investigation found that Whitey's FBI handler, John Connolly, had falsified information in his informant reports (a detail addressed in the movie), in part to steer authorities away from Whitey and in part to make Whitey look like a valuable informant (

In 2008, former FBI agent John Connolly was convicted of second-degree murder after already being convicted in 2002 for a 1999 indictment on charges of accepting bribes, protecting Bulger and his gang from prosecution, and alerting them to informants in their ranks. Connolly's former FBI supervisor, John Morris (portrayed by David Harbour), testified that he himself took bribes from Bulger in the amount of $7,000, along with a silver-plated champagne bucket and two cases of imported wine. Morris said that Bulger even paid for a plane ticket so his girlfriend could visit him. -CNN

Did Whitey Bulger really strangle Deborah Hussey?

Yes, as conveyed in the Black Mass movie, Bulger's right-hand man, Stephen Flemmi (portrayed by Rory Cochrane), had sex with Deborah Hussey, the daughter of Flemmi's common-law wife, Marion. Flemmi had moved in with Deborah's mother when Deborah was a toddler. He had helped to raise her and she even called him "Daddy." By the time she was 26, she had become a drug user and was deemed a problem for the gang. Flemmi took her shopping and then lured her into his mother's home, where he says Whitey Bulger strangled her in the basement. The movie changes this a bit and has Flemmi and Bulger bring her gifts when they pick her up and take her back to Flemmi's mother's house, but the end result is the same.

After being questioned about his sexual relationship with Deborah Hussey, Flemmi testified that Bulger had engaged in a relationship with a 16-year-old girl who he took to Mexico with him, an alleged crime that is not addressed in the movie.

James "Whitey" Bulger strangled Deborah Hussey (left) in 1985. Her teeth were pulled from her skull (right) and her body was buried in the basement of a South Boston home. Juno Temple (center) portrays Hussey in the movie.

How long was Whitey Bulger on the run?

On December 23, 1994, Whitey Bulger's former FBI handler, John Connolly, warned him about a pending indictment under the Racketeer Influenced and Corrupt Organizations Act (RICO) ( Whitey fled Boston and went into hiding for more than 16 years. At age 81, he was captured in Santa Monica, California on June 22, 2011 along with his girlfriend, Catherine Greig. She was portrayed by Sienna Miller, but the actress's role was cut from the final version of the movie. During his time on the run, he and Catherine hid in various locations, including New York; London; Chicago; Grand Isle, Louisiana; and ultimately Santa Monica (

Was Whitey Bulger the FBI's 2nd most wanted fugitive behind Osama bin Laden?

Yes. The Black Mass true story confirms that Whitey was added to the FBI's Top 10 Most Wanted list in 1999, facing charges in 19 murders. After Osama bin Laden was killed in 2011, Whitey moved into the top spot on the list. By then, the FBI was offering a $2 million reward for tips leading to Whitey's capture and a $100,000 reward for tips resulting in the apprehension of his girlfriend, Catherine Greig. It was the largest reward ever offered for information on a U.S. fugitive. -FBI

How was Whitey Bulger captured?

Though it's not shown in the movie, a break in the case came following the release of a public service announcement by the FBI. The PSA included newly recovered images of Bulger's girlfriend, Catherine Greig. The photos were discovered after the FBI traced the serial numbers from Catherine's breast implants back to the plastic surgeon's office. The office had a file with photos of Catherine taken for the surgery. A former neighbor recognized Catherine from the photos in the PSA and the tip was relayed to the FBI's LA office. That information led to the capture of Whitey Bulger and Catherine Greig on June 22, 2011 at an apartment building in Santa Monica where they were living. -DailyMailOnline

The FBI set up a ruse with the building's landlord, who called the apartment and told Catherine that their storage locker had been broken into. When Whitey went down to the basement to see if anything had been stolen, the FBI was waiting to take him into custody. The movie changes this a little and shows Whitey being taken into custody as he walks into the building's basement parking garage. -CBS This Morning

FBI agent Scott Garriola (left) takes an 81-year-old Whitey Bulger into custody in the basement of his California apartment building in 2011.

How much money did Whitey Bulger have when he was captured?

The Black Mass true story reveals that Whitey had in excess of $822,000 and 30 guns hidden in the walls of the apartment that he shared with girlfriend Catherine Greig. -DailyMailOnline

What happened to Whitey Bulger's girlfriend, Catherine Greig?

Whitey's girlfriend, Catherine Greig, was sentenced to eight years in federal prison for aiding and abetting a fugitive. She was portrayed by Sienna Miller in a role that was cut from the final version of the movie. "It came down to narrative choices," director Scott Cooper told The Boston Globe. -DailyMailOnline

What was corrupt FBI agent John Connolly's punishment for aiding Whitey Bulger?

In 2009, John Connolly, portrayed by Joel Edgerton in the Black Mass movie, was sentenced to 40 years in prison on second-degree murder charges for the 1982 mob-related killing of accountant John Callahan by Winter Hill hitman John Martorano. The hitman left Callahan's bullet-riddled body in the trunk of his Cadillac in the Miami International Airport parking lot. The hit was allegedly ordered by Whitey Bulger and Stephen Flemmi. During the trial, jurors heard that Connolly had informed his mob connections that John Callahan might be a possible witness against them in relation to the May 1981 murder of Roger Wheeler, a businessman. -CNN

John Connolly had already been serving a 10-year federal prison sentence stemming from a 2002 racketeering conviction related to his corrupt dealings with Bulger's gang.

Former FBI agent John Connolly (left) was sentenced to 40 years in prison for tipping off Whitey Bulger.

Did Whitey Bulger's story inspire any other movies?

Yes. In the 2006 Martin Scorsese movie The Departed, Irish Mob boss Frank Costello (Jack Nicholson) and his mole in the Massachusetts State Police Department, Colin Sullivan (Matt Damon), were loosely inspired by Irish-American Gangster Whitey Bulger and his corrupt FBI handler John Connolly.

Whitey Bulger Interview & Related Videos

Listen to the voice of the real Whitey Bulger below and watch the FBI's PSA that led to the capture of Whitey and his girlfriend Catherine Greig.

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