Biography of James Whitey Bulger, Notorious Crime Boss

Whitey Bulger Mugshot
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James “Whitey” Bulger (September 3, 1929–October 30, 2018) was an infamous Irish-American crime boss associated with the Winter Hill Gang in Boston, Massachusetts. He was given the nickname “Whitey,” a name he greatly detested, because of his pale skin and fair blond hair. In June 2013, at age 85, he was convicted of dozens of counts of racketeering, including complicity in eleven murders.

Fast Facts: James "Whitey" Bulger

  • Known For: Notorious crime boss who led Boston’s Winter Hill Gang in the 1970s and 80s
  • Born: September 3, 1929 in Everett, Massachusetts
  • Parents: James Joseph Bulger Sr. and Jane Veronica "Jean" Bulger
  • Died: October 30, 2018 in Preston County, West Virginia

Early Life

Bulger was born in Everett, Massachusetts on September 3, 1929, but later moved to a housing project for low income families in South Boston along with his parents, two sisters, and two brothers. One of his brothers, William, would go on to be the president of the University of Massachusetts as well as of the Massachusetts State Senate. In school, he was cited for being restless and argumentative with both the nuns at his Catholic school and the teachers from his later years in public school.

Starting at age 13, Bulger was frequently arrested, sometimes for violent crimes but more often for larceny and other thefts. In many instances, the cases were dismissed, or Bulger was found not guilty, or he won an appeal.

In January 1949, Bulger joined the Air Force for nearly four years. Despite being arrested for robbery, rape, desertion (AWOL), and grand larceny, he was never sentenced and instead was honorably discharged from the Air Force in August 1952.

Prison Sentence

Upon his return from the Air Force, Bulger resumed his criminal behaviors, robbing freight trains and selling the contents on the street. Eventually, he connected with Carl Smith, an Indiana bank robber, with whom he stole tens of thousands of dollars from banks across the United States.

Despite dying his hair in an attempt to avoid recognition, Bulger was arrested in a Boston nightclub for armed robbery of the various banks. He willingly named his associates, including Smith, in exchange for leniency. Regardless of this cooperation, he was sentenced to 20 years in a federal penitentiary. He first served in Atlanta Penitentiary where he was a subject of the CIA’s MK-ULTRA experimentation, which researched methods of mind control in exchange for a lessened prison sentence. He was transferred three times before being granted parole in 1965 after serving nine years.

Winter Hill Gang

Bulger returned to find Boston in the midst of a gang war. He began working for the Kileen Brothers, then turned on the Kileen gang and began to side with the Mullen Gang, then finally joined the Winter Hill Gang with his close partner Steve Flemmi.

In 1971, Bulger and Flemmi were approached by FBI agent John Connolly, who grew up with the Bulgers and even looked up to Whitey’s younger brother Billy. The two gangsters became informants for the FBI, whose main objective was taking down the Italian Mafia. With the protection of the FBI, Bulger began to put out hits on long-standing enemies, knowing that he could easily mislead his handler by pointing to someone else as the perpetrator. Flemmi and Bulger also killed Flemmi’s long term girlfriend Debra Davis, since she knew of their relationship with the FBI. Though she was officially reported missing, the FBI allegedly covered this up and reported that she was seen alive in Texas.

Connolly consistently tipped of Bulger and Flemmi to the FBI’s investigations and he became a fierce protector of the two gangsters. Many others within the FBI and the Massachusetts State Police consistently protected them as well.

Bulger and Flemmi quickly became the ring leaders of Boston’s organized crime as they took over leadership of the Winter Hill Gang. During this period in the 1980s, they became involved in arms trafficking, further racketeering, and extortion of drug dealers, among other things. He was especially involved in supporting the Irish Republican Army by sending caches of arms and ammunition to the Irish terrorist organization.

Downfall and Manhunt

In 1994, the Drug Enforcement Administration, the Massachusetts State Police, and the Boston Police began investigating Bulger and his associates for gambling charges (not any of the murders). Connolly, who had since retired, warned Bulger about the impending arrest. Bulger fled Boston in December 1994.

Flemmi refused to flee and was imprisoned, but cooperated with the authorities understanding that he was protected as an FBI informant as long as he did not admit to any murders. However, Bulger’s other associates, realizing that Flemmi would name them in his testimony, told investigators about the murders that took place throughout the 1970s and 1980s. John Martorano and Kevin Weeks provided most of the information which also led to the realization that the FBI had been instrumental in covering up many of the murders.

In 1999, former agent Connolly was arrested for alerting Flemmi and Bulger to the FBI’s impending arrest. A year later, he was charged for racketeering and second degree murder, since the information he provided the two men led to their decision to kill the two men whom were under investigation for ties to the Winter Hill Gang. He was given a 10 year federal sentence and 40 year state sentence.

During this period, Bulger was still at large with his girlfriend Catherine Greig. For 16 years, he moved around the U.S., Mexico, and Europe without capture. He was eventually found and captured in his Santa Monica apartment after an intense media campaign in which he was consistently featured on programs such as America’s Most Wanted.

Convictions and Death

Bulger was ultimately convicted of 31 counts of racketeering, after he pled not guilty to 32. Of these counts he was also charged for 11 out of the 19 murders that he was indicted for. On November 23, 2013, Bulger was sentenced to two consecutive life sentences plus 5 more years. He has also been indicted in Oklahoma and Florida, but the two states have yet to pursue a trial which could end in the death penalty. At age 85, Bulger entered United States Penitentiary Coleman II in Sumterville, Florida. On October 29, 2018, he was transferred to the Federal Penitentiary in West Virginia. The next morning, he was killed by multiple inmates at the penitentiary.

James “Whitey” Bulger’s legacy remains that of a notorious Boston crime boss who kept relationships with both state police and the FBI, which allowed him to conduct massive criminal operations for decades. Although Bulger made claims that he was never an FBI informant, a litany of witness testimony and other evidence contradicts these assertions. Because of his association with the FBI, Bulger lost much of his prestige within crime circles and is sometimes referred to as the "King Rat."

Sources

  • Cullen, Kevin. Whitey Bulger: America's Most Wanted Gangster and the Manhunt That Brought Him to Justice. Norton, 2013.
  • “Whitey Bulger Bio Profiles Boston's Most Notorious Gangster.” New Hampshire Public Radio, 2014, www.nhpr.org/post/whitey-bulger-bio-profiles-bostons-most-notorious-gangster#stream/0.
  • “Whitey Bulger: The Capture of a Legend.” The New York Times, The New York Times, 2 Aug. 2013, archive.nytimes.com/www.nytimes.com/interactive/us/bulger-timeline.html#/#time256_7543.