Balding, with freezing blue eyes and a lopsided smirk on his face, Johnny Depp completely internalized underworld kingpin James “Whitey” Bulger in the dark drama “Black Mass”.

His look, his voice, everything about him gave me the creeps!


The three-time Oscar nominated actor nailed Whitey’s character, from his swaggering physique to his fragmented psyche.

Of course, the make-up department got Whitey’s visage down pat, with sculpted silicone facial prosthetics, measured to the exact distance of his hairline, nose, lips and eyes.

Tell that to people who knew the flesh-and-blood crime lord with the rock star charisma surpassed only by Osama Bin Laden at the top of America’s Most Wanted List.


So convincing was Johnny Depp as Whitey, they all drew back terrified when he sauntered on the set.

Well, I enjoy being frightened, but I wasn’t prepared to be utterly transfixed by this gangster biopic.

“Black Mass” recounts the unholy alliance between men of the law and Irish-American mobsters versus La Cosa Nostra, the Italian Mafia, in Boston, Massachusetts.  It was a sellout to the devil himself.


The tale revolved around Whitey, a small-time racketeer- loan-shark-with-the-occasional-murder-turned-NBI-informant. He evaded law enforcers and gained so much power he became one of the most dangerous gangsters in U.S. history.

For over a decade, the FBI hunted him down. They captured him in 2011 and put him behind bars last year. He’s 86 years old now, serving two life terms plus five years for racketeering, 19 counts of murder, extortion and distributing narcotics, among others.

Directed by Scott Cooper, the powerhouse cast of “Black Mass”  consists of Joel Edgerton as FBI Agent John Connolly; Benedict Cumberbatch as Whitey’s brother, State Senator Billy Bulger; Rory Cochrane as Stephen Flemmi, Whitey’s closest partner in crime; Jesse Plemons as Whitey’s main henchman, Kevin Weeks and Kevin Bacon as FBI Special Agent in Charge Charles McGuire.

The notion that the FBI would have high level mob people working for the Bureau—or the FBI thinking they’re working for them – was what drew Producer Brian Oliver to the film. “It shows anybody can get sucked down the rabbit hole.”

It all began in the 1970’s, when FBI Agent John Connolly came home to a hero’s welcome in South Boston after arresting a top Mafioso in New York.


To climb on top of the career ladder, he had to bring down Boston’s Cosa Nostra. Blinded by ambition, he persuaded his childhood friend, Whitey Bulger, to collaborate with the FBI to eradicate their common enemy: the Mafiosi.

From hereon, he was trapped like an insect in a spider’s web, shielding his informant, turning a blind eye on all his dealings. Whitey takes over the Winter Hill Gang and expands his criminal empire.

The biggest irony was, Whitey would never have done that without the aid of the FBI.


“You’re talking about a man without conscience who’s extremely bright and cunning. Now, he has unfettered access to all levels of crime in the city and the ability to do whatever he wants,” Director Scott pointed out. “That’s a recipe for disaster. Ultimately, it became the biggest scandal in the history of the FBI.”

Yet John allowed Whitey to run amok in the city, wanting to be in the crime lord’s good graces ever since Whitey rescued him in a playground fight when they were kids. He grew up with Whitey and his brother, Billy Bulger, in Southie, a small enclave of South Boston.


“Many idolized him. Many wanted to be him because he did things his own way and, for the most part, he won.  But he was also a very charismatic man,” was how Johnny Depp described one of America’s Most Wanted Man.

People feared him, yes, but many others looked up to him as a Robin Hood figure. “He’s a fascinating character and I was interested in what drove him.”


“I think John saw Whitey as a renegade who had this rock star glow about him,” Joel says of his character. “John aspires to be a great lawman. But on his home turf, the line between crime and the law is blurred. And if the person you admired was on the other side of the law, it could lead to other aspirations. He got intoxicated by the boundless freedom with which criminals operate.”

John’s fascination with Whitey is universal, Producer John Lesher observed.


“People are intrigued by gangsters. They live by different rules than the rest of society.  Here, you have a close tie between a notorious gangster, whose brother happens to be the most powerful politician in the state and a star FBI agent.”

Interestingly, Director Scott calls Johnny’s Whitey Bulger “a character unlike any he’s ever played”.


“Whitey could be charming, but he was also a man who, in the blink of an eye, would just as soon kill you as look at you.  Johnny understood that Whitey is not a likable character for the most part. There’s a very vicious side to him, which you’ve never seen before from Johnny.”


“But he wanted to create a full-bodied portrait—to show Whitey as flawed as he is maniacal, ruthless but also human. It’s dangerous because we don’t want people to say we’re humanizing someone who personified evil.  We certainly showed all levels of his brutality.  He was a stone-cold killer and Johnny played that to the hilt.  He went to great lengths to create his performance through a tremendous amount of research.  From the way he moved to the timbre of his voice, he was able to fully inhabit the sociopath that was Whitey Bulger.”

What’s more disturbing, “Johnny really looked like Whitey,” stressed Dick Lehr, one of the authors of the “Black Mass” book on which they based the film.  “He had that same body language and swagger.  It was eerie and very effective.”

Fellow actor Joel explored John Connolly’s psyche just as arduously.


Success seduced John. So, in his mind, the ends justify whatever means are necessary, Joel surmised.

“John wants to be celebrated and admired by everyone.  But that takes him to dark places. He becomes so enmeshed with Whitey he doesn’t realize how deep he’s gone, how irretrievable his conscience is. His whole life becomes dismantled by this obsessive relationship and by this need to be constantly affirmed by a criminal.”

To complicate matters, John wears so many masks, his director stressed.

“With his wife he’s one thing; with Billy Bulger he’s another; with Whitey, yet another. Of course, he has a completely different mask when he’s around his FBI colleagues.  Joel delivered such a nuanced performance, perfectly capturing Connolly’s bravado and his preening peacock confidence, as well as his vulnerability and searing weaknesses.  In fact, when the real Fred Wyshak, who had known Connolly for years, came to visit the set, he said Joel was ‘nailing everything about him in every way.’  He’s extraordinary.”

The filmmakers admitted taking creative license in dramatizing the real-life events “because it would be impossible to portray everything in a single movie”. Yet overall, the story is based on real events.

The revelation that Whitey Bulger was informant for the FBI made headlines in The Boston Globe in 1988. Then-Globe reporters Dick Lehr and Gerard O’Neill, who broke the story, later wrote the book Black Mass: Whitey Bulger, the FBI, and a Devil’s Deal.


Initially, they conceived it as a tale of two brothers: Whitey and Billy, who grew up in the same house in the South Boston projects and ended up at the top of their respective games, albeit with very different rules.

Billy Bulger’s game was politics.  College educated, his career trajectory was the polar opposite of his criminal brother’s, taking him all the way to the presidency of the Massachusetts State Senate.

Benedict Cumberbatch, who played Billy, concurs that the dichotomy between the two brothers was an intriguing angle to pursue.


“Billy Bulger was a powerful political figure for many years in the State Senate.  If you wanted anything done, you went through him.  On the other hand, he’s the brother of Whitey Bulger and is fatefully entwined with the most infamous criminal of the 20th century.  It’s a fascinating divide, a great tension to play in a character.”

“Billy went his way and became this very highfalutin’ politician, and Jimmy went his way and ended up a king of the underworld,” Johnny acquiesced.  “Yet they visited their mom and were a close family even though they were on distinctly different sides.”

Nevertheless, Benedict refused to make a judgement whether Whitey was protecting Billy and vice versa.  “I left that alone. I focused on the fact that they were brothers who loved each other. Let the audience come to their own conclusions.”

The writers of the “Black Mass” book themselves pursued the brothers’ divergent paths until they uncovered a more hideous twist.

“Even though Whitey was an acknowledged crime boss, he eluded the authorities with a magical touch,” Dick explained. “As we peeled the layers of the onion, we found that within local law enforcement, they’ve long suspected something funny was going on between Whitey and the FBI.”


“Once we established that Whitey was an FBI informant, we let the genie out of the bottle,” Gerard went on.  “Informants are the Holy Grail of the FBI and, in turn, the ‘wise guys’ want a friend in law enforcement, so it’s a symbiotic relationship. “

Nevertheless, “I don’t think Whitey Bulger would have been an informant for anyone who wasn’t from Southie. Connolly was able to use his hometown connection and was recognized and rewarded for having Whitey as an informant, but it was Whitey who was in control.”

“We didn’t know how deep and dark and horrifying it was. That took years to tumble out. But the story opened the door to what later became this epic saga and the historic scandal involving Whitey and the FBI.”

“It became a case of the tail wagging the dog,” the scriptwriters remarked. “This force Connolly hoped to harness on behalf of the FBI ended up the other way around, with Whitey holding the reins.  Anyone who wasn’t so embroiled with Bulger would probably have recognized what was happening, but Connolly didn’t.”


And so, Black Mass, the film, dissected the bonds of brotherhood and misguided loyalties, set against unbridled ambition and avarice, an almost Shakespearean tragedy and hubris.

There are no good guys here. It’s a story of criminals who happened to be human, just as it’s a story of humans who happened to be criminals in a time and place where no one can draw the boundaries between lawmen and lawless.


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