Who was Whitey Bulger? Boston man arrested in connection to 1984 murder of mobster

Michael Lewis, a criminal linked to notorious crime boss Whitey Bulger, is being charged with the 1984 murder of alleged drug dealer Brian Watson.

While Whitey Bulger was not directly involved in the case, it was partially his reputation and influence that led to Watson's murder. Once a prominent organized crime figure in the city, Bulger was known to extort several drug dealers. According to CBS, Watson was murdered for informing Bulger that one of Lewis’ associates had been dealing drugs, making him an extortion target for the notorious crime boss.

Federal authorities reported that they had pinned Lewis as the primary subject in 2009, but were unable to secure an indictment due to a lack of evidence. This year, however, there were new developments in the case, leading to Lewis’ detainment. The alleged gunman, now 61-years-old, pleaded not guilty to the charges.

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Whitey Bulger, Former Gangland Boss

From the 70’s to the 90’s, Whitey Bulger had established himself as the most influential leader of Irish American organized crime in Boston. The gangster became a mainstay in American popular culture. He was depicted by Jack Nicholson in the 2006 film, The Departed, and Johnny Depp in 2015's Black Mass.

The mobster grew up in South Boston, once home to several Irish-American gangs. As a young man, Bulger was drawn into criminal activity, experiencing his first arrest at age 14. Despite a brief period in the Air Force, he returned to criminal life, with numerous arrests linking him to activities such as assault, theft and hijacking.

In the 1960’s, Boston saw a series of gangland killings as criminal elements fought for control over illegal businesses within the neighbourhood. By 1972, Bulger had established a reputation among organized crime figures for his ruthlessness, rising to become the leader of the notorious Winter-Hill gang.

However, Whitey Bulger’s true influence emerged due to his relationship with childhood friend and FBI agent, John Connolly. Connolly had been friends with the politician brother of the gangster, William Bulger, who would go on to become President of the Massachusetts Senate. Using these connections in law enforcement and politics, Bulger managed to evade arrest while assassinating and informing on his rivals, establishing his control over the Boston underworld.

In 1994, Whitey Bulger’s empire began to crumble after the DEA, Boston Police, and Massachusetts State department began targeting his gambling operations. Following a tip off from John Connolly, Bulger fled Boston and lived as a fugitive while various members of his gang were arrested. In 2005, Connolly himself was indicted on murder charges for assisting Bulger in planning the gangland killings of John B. Callahan and Roger Wheeler in the 80’s.

After 16 years in hiding and 12 years as one of FBI’s most wanted fugitives, Bulger was arrested in 2011 in California. The 81-year-old pleaded not guilty to 48 charges, which included extortion, narcotics distribution and 19 murders. In 2013 he was convicted of 11 murders.

In 2018, after serving five years of his life sentence, a wheelchair-bound Whitey Bulger was beaten to death by fellow inmates with organized crime links. According to NBC, it is believed they murdered him due to his history as an FBI informant. Bulger’s family attempted to sue the federal prison over his murder, but this was to no avail.

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Who is Michael Lewis?

According to the Press Herald, Bulger's dominant presence in the Boston Underworld was a major catalyst in the murder of Brian Watson.

CBS reported the prosecution's account of the events, detailing what led to Watson’s 1984 murder. It is alleged that after Watson reported the involvement of Lewis’ friend in the drug trade, Whitey Bulger demanded a payment of $5000 from this friend, as well as $1000 per week. This was a regular source of income for Bulger, who used his influence to extort drug dealers across South Boston.

According to prosecutors, as retribution for informing Bulger, Lewis and his friend took Watson on a drive.

Prosecutor John Verner told the court:

“During that ride, Michael Lewis, who had a semi-automatic firearm with him, turned around and shot him.”

According to Boston25, in September 1984 Watsons body was found along I-93 South in Manchester, New Hampshire. While the case remained unsolved for nearly 40 years, a witness recently provided testimony that was consistent with evidence connected to the murder.

Lewis, however, pleaded not guilty to the charges.

His defense attorney, James Sultan, told The Associated Press:

“(Lewis) adamantly denies the allegations and looks forward to his day in court.”

According to Suffolk District Attorney Kevin Hayden, the trial of Michael Lewis has reminded many Bostonians of a darker period in the city’s history, when Whitey Bulger terrorized various neighbourhoods.

He said:

“We had a glimpse in the courtroom today of a very different Boston, a Boston that we can never allow to happen again. After nearly 40 years we are reminded of the mayhem and murder inflicted by cold-hearted and corrupt, cruel men.”

While Whitey Bulger was not directly linked to the murder, it was indicative of the powerful presence he had over Boston underworld figures during the violent era.