Power Quotes in Black Mass: Whitey Bulger, the FBI, and a Devil's Deal

How we cite our quotes: (Part.Chapter.Paragraph)

Quote #1

Connolly, properly obsequious to a neighborhood elder who was also an icon, made his offer: "You should think about using your friends in law enforcement." (1.1.11)

Does this seem like the right way for an FBI agent to deal with a known gangster? Does being a "friend" to a crime lord count as a justified use of federal power? If you answered "yes" to either one of these questions, then you might be John Connolly. Hiya John.

Quote #2

At once [Billy] was a petty despot and a masterful conciliator, [...] a puckish public performer who had a dark side and took all slights personally. (1.2.21)

Whitey isn't the only bigwig Bulger bossing it up in Boston—there's also brother Billy, state senator and grouch extraordinaire. Despite being more "legit" than his big bro, Billy is just as willing to throw his weight around to get what he wants. They call that Bulger style.

Quote #3

Like a drug, their ties to Bulger and Flemmi had evolved into a dependency that was hardening quickly into an addiction. (1.5.89)

The FBI's relationship with Bulger and Flemmi certainly has its benefits. It gives the FBI a leg up in the mob, and Flemmi's intel helps them break several major cases. But there's a downside: the longer they're together, the more Bulger dominates the relationship.

Quote #4

They saw only what they wanted to see. It was a moment built on a shared premise: the future belonged to them. (1.5.90)

Bulger, Flemmi, Connolly, and Morris create their own little slapdash gang, distinct from both the FBI and the criminal underworld. Their goal? Make sure that each of them becomes as powerful as possible. Where do we sign up?

Quote #5

1980 was a time when both Bulgers were consolidating their power and fast approaching the top of their games. (2.6.11)

As the decades chug along, the Bulger boys only gain more power for themselves: Billy in the state senate, and Whitey in the mean streets of Southie. In fact, both men become so powerful that they become inescapably linked to South Boston itself.

Quote #6

[B]oth sides knew that the wary collaboration between Bulger and the Mafia was the cornerstone of organized crime in Boston. (2.8.49)

The irony of all ironies is that Whitey isn't only getting help from the FBI: he's also getting help from the Mafia, which he's also helping the FBI destroy. He's not just playing both sides like a fiddle—he's conducting a legit orchestra.

Quote #7

Roger Wheeler may have been a multimillionaire [...] but [...] Wheeler was just another guy in Whitey Bulger's way. (2.10.11)

The assassination of Roger Wheeler is Bulger's boldest move ever. He's killed plenty of people already, but none were as prominent or as well-connected as Wheeler. It just goes to show how powerful this project-born ex-con has become.

Quote #8

By this time John Connolly had emerged as the kind of quintessential public figure for the 1990's, a decade increasingly obsessed with style and celebrity. (3.20.108)

Whitey isn't the only one gaining steam: Connolly's making major moves himself, emerging as a minor celebrity. Okay, okay, so he might not break C-tier, but that's pretty impressive for an FBI agent. And you can believe that Connolly is going to milk his 15 minutes for everything they're worth.

Quote #9

He was sentenced to forty years in prison [...] all the bluster had gone out of the Connolly balloon. (e.51)

And then, just like that, it's all gone. All that bravado, all that swagger, all that bullying and macho posturing—gone in an instant. A lifetime sentence in federal prison will do that to a guy.

Quote #10

For the first time eve Whitey Bulger's younger brothers began to pay a price [...] for their boundless loyalty to the crime boss and killer. (e.60)

The Bulger brothers were more than willing to use Whitey to their own benefit, so it's only fair that they're knocked down a peg when his corruption is revealed. Given the Bulgers' prominence in South Boston, this is a massive scandal in the community.