James (Whitey) Bulger

Organized crime figure

• Born: September 3, 1929
• Birthplace: Boston, Massachusetts
• Died: October 30, 2018
• Place of death: USP Hazelton, West Virginia

Organized crime figure

Also known as: James Joseph Bulger Jr.

James "Whitey" Bulger was a prominent organized crime leader who worked primarily out of South Boston from the early 1970s to the early 1990s. He was arrested in June 2011 after more than a decade on the FBI’s list of the ten most-wanted fugitives.

As a teenager, Bulger was known around as a street fighter. He was first arrested in 1943 at the age of fourteen and charged with larceny. In 1948, he enrolled in the US Air Force and was given an honorable discharge in 1952. He returned to Massachusetts, where he increasingly became involved in organized crime.

Bulger was arrested and sentenced to prison in 1956 for armed robbery and hijacking. There, he volunteered to be a test subject in various experiments with the hallucinogenic drug LSD. In return, his twenty-year sentence was commuted. He was released in 1965 after serving nine years in prison.

After his release, Bulger became a bookmaker and loan shark, developing close ties with the leaders of Boston’s Irish mob. In 1974, he became an informant for the Federal Bureau of Investigation (FBI), which was beginning to investigate the Italian mafia in Boston, particularly the Patriarca crime family. The relationship between the FBI and the mob caused much controversy, as it was believed the FBI was willingly covering up the mob’s criminal activities in exchange for information and bribes.

Over twenty years, Bulger became head of the Winter Hill Gang. He was helped greatly by his status as an informant. Bulger, along with his associates Stephen Flemmi and Kevin Weeks, committed murder, racketeering, extortion, and money laundering.

After being tipped off by a connection in the FBI that he was about to be arrested in December 1994, Bulger fled Boston and hid out until his arrest on June 22, 2011, in Santa Monica, California. On November 24, 2013, Bulger was sentenced to two consecutive life terms plus five years in prison.

Background

James Joseph Bulger Jr. was born on September 3, 1929, in Boston, Massachusetts. His father was a blue-collar laborer and stevedore who had lost one of his arms in an accident. Due to this, the family fell into poverty and had to relocate to housing projects in South Boston in 1938. Bulger had five younger siblings. His brother William later rose to prominence as a politician in Boston and served as the president of the Massachusetts Senate and president of the University of Massachusetts.

Bulger was given the nickname "Whitey" as a child because of his bright blond hair, although he was not fond of the name and preferred to be called Jimmy. He did not perform well in school and was an unruly teenager who frequently got into fights. He never graduated from high school. Instead, he joined a street gang known as the "Shamrocks," and at age fourteen he started having his first run-ins with the police, who arrested him on charges of armed robbery and larceny.

After serving time in a juvenile reformatory, Bulger enlisted in the US Air Force in 1948 and was stationed in Kansas and Idaho. During his time in the Air Force, he continued his violent ways and was reprimanded several times for fighting. After receiving an honorable discharge in 1952, Bulger returned to Boston. He became increasingly involved in crime, and he was arrested for armed robbery and hijacking in 1956.

Bulger was sent to the Atlanta Penitentiary in Atlanta, Georgia. He was later transferred to Alcatraz Federal Penitentiary on Alcatraz Island in San Francisco, California. Due to his volatile manner, he was sent to solitary confinement numerous times. After Alcatraz shut down in 1963, Bulger was transferred to Leavenworth Federal Penitentiary in Leavenworth, Kansas. There, Bulger volunteered to be a test subject in an experimental study that tested the effects of the hallucinogenic drug LSD. The study was performed by the Central Intelligence Agency’s (CIA) Scientific Intelligence Division, which told the prisoners they were testing a cure for schizophrenia. In reality, the tests were part of the controversial Project MK-Ultra, which experimented with the behavioral engineering of humans through drugs.

After Alcatraz, Bulger was transferred once more, this time to Lewisburg Federal Penitentiary near Lewisburg, Pennsylvania. For his participation in the LSD experiments, Bulger’s twenty-year sentenced was reduced, and he was released after only serving nine years.

Mob Leader and FBI Informant

When Bulger returned to Boston after his release from prison in 1965, he found work as a bookmaker and loan shark, becoming increasingly involved with mob activity in South Boston. Howie Winter was the leader of the Boston mob, dubbed the Winter Hill Gang by local newspapers, which also included Bulger’s friend Stephen "The Rifleman" Flemmi, an Italian American criminal. Bulger and Flemmi became enforcers for the gang, violently collecting debts as well as helping to fix horse races by bribing jockeys.

In 1974, Bulger began his relationship with the FBI as an informant for their investigation of the Italian mafia in Boston, particularly the Patriarca crime family in Boston’s North End. Flemmi was already an informant by this time and Bulger was recruited by Special Agent John Connolly, who had grown up in the same neighborhood as Bulger. Bulger eventually agreed, joining the FBI’s Top Echelon Informant (TEI) program.

After Winter Hill Gang member Anthony "Fat Tony" Ciulla named Winter, Bulger, and Flemmi as leaders of race-fixing operations in 1979, Winter was convicted. Nonetheless, the FBI kept Bulger and Flemmi out of the case. With Winter in prison, Bulger became the new leader of the Winter Hill Gang. As head of the gang, Bulger established a new approach to their criminal activities and used his connections in the FBI to eliminate his competition in Boston through arrests. Bulger and his associates began extorting protection money from bookies and drug dealers who wanted to operate within the Winter Hill Gang’s territory. This money was referred to as "rent." Those who refused to pay were harassed, threatened, assaulted, or murdered.

Thanks to his privileged status with the FBI, Bulger and his associates were protected from allegations against them. An enforcer named Brian Halloran approached FBI claiming to have witnessed Bulger and another gang member murder a bookie in a bar in South Boston on April 12, 1980. They allegedly dumped the body in the trunk of the victim’s car. Halloran also alleged that Bulger ordered the murder of Roger Wheeler, the owner of World Jai Alai, a sports-betting company with offices in Connecticut.

Halloran feared for his life, so he went to the FBI to exchange information for protection. However, once Connolly heard about Halloran’s confession, he arranged it so that Bulger would not be arrested and that Halloran’s testimony would be deemed untrustworthy. Halloran was subsequently turned away from an FBI safe house and, on May 11, 1982, Halloran was murdered as he left a bar in South Boston.

Bulger and his gang were linked to other murders, but Connolly protected them from local and state police investigations by refusing to turn over evidence and by exaggerating Bulger’s value as an informant. Bulger also bribed FBI agents to be informed about investigations into his actions. With the help of Connolly, Bulger was free to manipulate organized crime rings in Boston to his favor.

Flight, Capture, and Conviction

Bulger maintained his hold over organized crime in Boston until December 1994. Connolly, who had retired from the FBI in 1990, informed Bulger that the FBI had received indictments against him from the US Department of Justice. Connolly also divulged that Bulger was to be arrested for racketeering, extortion, and violations of the Racketeer Influenced and Corrupt Organizations Act (RICO). This act was created in 1970 to convict organized crime members who not only committed illegal acts but who ordered others to commit crime, as well.

Bulger initially fled Boston with his girlfriend Theresa Stanley, however, she wanted returned to Boston soon afterward. He was later joined by another girlfriend, Catherine Greig, and together they hid out for sixteen years, being sighted in Wyoming, Mississippi, California, and London, England. After twelve years on the FBI’s list of most-wanted fugitives, Bulger was eventually apprehended in Santa Monica, California, on June 22, 2011. After a two-month trial, he was found guilty on August 12, 2013, of thirty-one counts of racketeering, money laundering, extortion, and illegal firearms possession. The jury also found that Bulger was complicit in the murder of eleven people. He was sentenced to two consecutive life terms plus five years on November 14, 2013. In December 2013, Bulger was transferred to a federal prison in Oklahoma City, Oklahoma. He was also indicted in Oklahoma for the murder of Wheeler in 1981 as well as in Florida, with the potential of facing the death penalty if convicted. In 2016, Bulger petitioned the US Supreme Court for an appeal in his case,. His argument was that during his trial he was not able to testify that he had been granted immunity. Not long after he was transferred to USP Hazelton in Bruceton Mills, West Virginia, in 2018, he was found beaten to death on October 30, 2018. He was eighty-nine years old.

Impact

As the leading figure of organized crime in Boston for decades, Bulger captured the nation’s imagination. Investigations into Bulger’s role as an informant for the FBI by the Boston Globe in 1997 exposed the criminal activities and corruption of state and federal law enforcement officers with ties to Bulger. The FBI received much negative criticism for seemingly allowing Bulger to commit criminal acts with impunity. His trial gained nationwide attention and was covered by most major media outlets.

Over the years Bulger became a famous mobster thanks in part to the great amount of media attention he received. Numerous books have been written about Bulger, most notably Black Mass: Whitey Bulger, the FBI, and a Devil’s Deal (2012), by Dick Lehr and Gerard O’Neill. Bulger was the inspiration for actor Jack Nicholson’s character in the 2006 crime film The Departed, directed by Martin Scorsese. A documentary about Bulger called Whitey: United States of America v. James J. Bulger premiered at the Sundance Film Festival in January 2014. The film, directed by Joe Berlinger, focuses on the trial of Bulger in 2013 and examines his relationship with the FBI. A fictionalized biopic film, Black Mass, was released in 2015, based on Lehr and O'Neill's book. Directed by Scott Cooper, it starred Johnny Depp as Bulger, with Joel Edgerton as Connolly and Benedict Cumberbatch as William Bulger.

In 2022, media reports indicated that Bulger was the victim of a planned murder in the West Virginia prison where he was being held. Three suspects were later arrested for the killing. One was alleged to be a member of a New York Crime family.

The figure of Whitey Bulger and his cooperation with the FBI continued to enthrall audiences in the next decades. In 2023, noted actor Neal McDonough announced he would portray Bulger in an upcoming TV miniseries.

Bibliography

Barr, Luke. "Whitey Bulger Killing was 'Planned' and Took Just 7 Minutes, Justice Department says."ABC News, 23 Aug 2022, abcnews.go.com/Politics/whitey-bulger-killing-planned-minutes-justice-department/story?id=88761649. Accessed 11 May 2023.

Cullen, Kevin, and Shelley Murphy. Whitey Bulger: America’s Most Wanted Gangster and the Manhunt That Brought Him to Justice. Norton, 2013.

Flatters, John. "Actor Neal McDonough Reveals Upcoming Role as Whitey Bulger in Saskatoon Appearance." CTV News Saskatoon , 8 May 2023, saskatoon.ctvnews.ca/actor-neal-mcdonough-reveals-upcoming-role-as-whitey-bulger-in-saskatoon-appearance-1.6390156. Accessed 11 May 2023.

Karas, Phyllis, and Kevin Weeks. Brutal: The Untold Story of My Life inside Whitey Bulger’s Irish Mob. Regan, 2006.

Keefe, Patrick Radden. "Assets and Liabilities." The New Yorker, 21 Sept. 2015, www.newyorker.com/magazine/2015/09/21/assets-and-liabilities. Accessed 12 June 2017.

Legare, Robert. "Whitey Bulger's Murder in Prison Exposed "Deeply Troubling" Failures, Justice Dept Watchdog Report Says." CBS News, 7 Dec 2022,www.cbsnews.com/news/whitey-bulger-death-justice-department-inspector-general-report. Accessed 11 May 2023.

Lehr, Dick, and Gerard O’Neill. Black Mass: Whitey Bulger, the FBI, and a Devil’s Deal. Public Affairs, 2012..

Lehr, Dick, and Gerard O’Neill. Whitey: The Life of America’s Most Notorious Mob Boss. Crown, 2013.

Mahony, Edmund H. "Witness Describes Hit on Gangster." Hartford Courant, 15 May 2002, www.courant.com/news/connecticut/hc-xpm-2002-05-15-0205151961-story.html. Accessed 28 Feb. 2014.

McFadden, Robert D. "Whitey Bulger Is Dead in Prison at 89; Long-Hunted Boston Mob Boss." The New York Times, www.nytimes.com/2018/10/30/obituaries/whitey-bulger-dead.html. Accessed 5 Dec. 2018.

Murphy, Shelley, and Milton J. Valencia. "Bulger Sentenced, Escorted From Sight." Boston Globe, 14 Nov. 2013, www.bostonglobe.com/metro/2013/11/14/james-whitey-bulger-sentenced-today/So7vvh343CUVY3Ey4g3pXO/story.html. Accessed 28 Feb. 2014.