Whitey Bulger: 5 Pop Culture Takes On Boston’s Irish Mob Legend

James "Whitey" Bulger/2011 mugshot [FBI]

BOSTON, MA — On June 22, 2011, FBI agents busted James “Whitey” Bulger outside a Santa Monica apartment building. The arrest had been a long time coming. With the click of those handcuffs, Bulger’s 16-year flight from justice — 12 of which he spent on the FBI’s Ten Most Wanted List — came to an end.

In the same moment, another chapter in the ongoing saga of Boston’s all-time most notorious crime lord just began — and the public wanted in on every detail.

Related: Whitey Bulger by the Numbers

Born in 1929, Bulger came of age in the famously hardscrabble Irish area of South Boston. He was nicknamed “Whitey” for his white-blonde hair, although he always hated that moniker.

As Bulger quickly took on the toughness and volatile attitude of an archetypal “Southie,” he took to crime early, landing in reform school at 14. He spent the rest of his youth in and out of other corrective institutions — including, in 1959, Alcatraz. At one point while behind bars, Bulger even volunteered for CIA experiments with LSD. He didn’t like it.

James “Whitey” Bulger/Alcatraz mug shot [WikiMedia Commons]

Related: Whitey Bulger Will Likely Die In Jail

In 1965, Bulger hooked up with local Irish mobsters and murdered his way to rapid prominence. By 1972, Bulger rose high in the infamous Mullen gang. Seven years later, he assumed the top position in the Winter Hill Gang.

Throughout the 1970s and ’80s, Whitey Bulger ruled the Boston underworld with no mercy and more than a touch of madness. His gangs all but decimated the local Italian Mafia.

Along the way, Bulger also killed innocents and shook down drug dealers to finance guns overseas for the Irish Republican Army. In 1991, Bulger even forced the winner of a legal $14 million lottery to cut him in on the winnings — deep.

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Somehow, Bulger consistently avoided going to jail for any of these transgressions. Later, the reason came to light: Bulger had been an FBI informant since at least 1974, working closely with Agent John Connolly — one of his close boyhood friends.

In 1994, various law-enforcement agencies concluded that Bulger had been protected by the FBI, and thus launched a three-prong investigation without the Bureau’s knowledge.

1980 FBI surveillance photo of Whitey Bulger and associate Stephen “The Rifleman” Flemmi [WikiMedia Commons]

Shortly thereafter, the Drug Enforcement Administration, the Massachusetts State Police, and the Boston Police Department built a monstrous case against Bulger and readied a take-down of his entire operation. Connolly tipped off Bulger and, in 1995, Whitey bailed from Boston. The 16-year-manhunt kicked off immediately.

Related: Alcatraz — Go Inside The Prison With Only 1 Successful Escape Attempt

Connolly faced his own justice 1999. Initially investigated for feeding info to Bulger, the FBI agent ended up going down also for taking bribes and for the 1973 murder of a Bulger target in Florida. He will die in prison.

On August 12, 2013, a jury found Whitey Bulger guilty of 31 felony counts of federal racketeering, extortion, and conspiracy, as well as 11 murders. He got two life sentences plus five years.

In the meantime — throughout all this insanity — Whitey’s brother, William “Billy” Bulger, grew up to serve in the Massachusetts Senate for 25 years before becoming the president of the University of Massachusetts for another seven.

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The contrast between the Bulger siblings does provide an operatic air to the story. As such, their tale has been made into numerous books, films, and songs. Here are five killer examples.

BROTHERHOOD (2006 – 2008)
Cast: Jason Isaacs, Jason Clarke, Fionnula Flanagan

The Showtime series Brotherhood based its three seasons on the dichotomy between real-life “good-and-evil” brothers William and Whitey Bulger, while moving the action from Boston to Providence, Rhode Island.

Jason Clarke stars as Tommy Caffee, an upstanding politician, while Jason Isaacs portrayed Michael Caffee, a homicidally ambitious thug in New England’s Irish Mob.

While never a huge hit, Brotherhood drew critical acclaim. Reviewers praised creator Blake Masters’ complex storytelling, along with the lead actors and supporting players such as Kevin Chapman as a crime lord and Annabeth Gish as Tommy’s wife. [Showtime]

Related: 7 Oscar-Winning True-Crime Movies — How Many Have You Seen?

THE DEPARTED (2006)
Director: Martin Scorsese
Cast: Jack Nicholson, Leonardo DiCaprio, Vera Farmiga

Adapted from the 2002 Korean cops-and-mobsters thriller Infernal Affairs, The Departed moves the action to Boston and fills the screen with a world-record amount of Hollywood actors attempting Southie accents (Mark Wahlberg, naturally, gets his right).

Jack Nicholson lords over the dastardly deeds and double crossings as Frank Costello, an Irish Mob boss clearly modeled on Whitey Bulger. The rest of the all-star cast includes Matt Damon, Leonardo DiCaprio, Alec Baldwin, and Martin Sheen as law-enforcement officers caught in Costello’s orbit.

The Departed picked up Academy Awards for Best Picture, Best Adapted Screenplay, Best Film Editing and — for the first time in legendary filmmaker Martin Scorsese’s career — Best Director. [IFC]

Related: Big Screen Crime Scenes — The Year in Notable Crime Films

“MORNING LIGHT (A BALLAD OF JAMES ‘WHITEY’ BULGER)” by Brendan Hogan (2011)

Through sheer coincidence, singer-songwriter Brendan Hogan released “Morning Light (A Ballad of James ‘Whitey’ Bulger)” in 2011, just shortly before the Feds finally nabbed the fugitive of the title.

Talking about the song to the press, Hogan said:

“As a Boston native, I wanted to pay homage to the city in a song and he’s the perfect character to have to do that. I knew I could do a whole album about him. The good brother, bad brother thing — it’s amazing … I assumed he was dead or long gone. Fast-forward to last week and, well, I’m glad I had the song ready.”

No one knows if Whitey himself has ever tapped his foot along to Hogan’s number. [Irish Central]

Related: 5 Dangerous Fugitives Who Were Nabbed In 2014

WHITEY: THE UNITED STATES OF AMERICA VS. JAMES J. BULGER (2014)
Director: Joe Berlinger

Connecticut native and true crime documentary maker extraordinaire Joe Berlinger (Brother’s Keeper, the Paradise Lost trilogy) brings personal passion to Whitey, his nonfiction film account of the entire Bulger case history.

Whitey serves as an excellent primer on the who’s-what’s-when’s-and-why’s of Bulgers rise, disappearance, and fall, and is bolstered by exclusive footage of the mobster attempting to explain himself.

As a result, some reviewers thought the film may have played too much into Bulger’s hands, particularly when he claims, despite reams of evidence to the contrary, that he never turned rat for the FBI. Still, it’s a mesmerizing two hours. [Mag Pictures]

Related: The 5 Most Unforgettable Mobster Nicknames

BLACK MASS (2015)
Director: Scott Cooper
Cast: Johnny Depp, Benedict Cumberbatch, Dakota Johnson

Black Mass represents Hollywood’s big swing at officially telling the Bulger brothers epic for the ages. As such, Johnny Depp makes a fine and frightening Whitey, while Benedict Cumberbatch brings depth to the part of Billy, the virtuous sibling who is not without his own human failings.

Joel Edgerton also scores as crooked FBI agent John Connolly and Rory Cochrane radiates sheer psychosis as Whitey’s right-hand murderer, Stephen “The Rifleman” Flemmi. [The Guardian]

Read more:
Biography
New York Times
CNN
New Yorker
The Mob Museum
Boston Globe

Main photo: James “Whitey” Bulger/2011 mugshot [FBI]