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

Here's one big reason why Bulger and Connolly hook up: they were practically next-door neighbors growing up. It also helps that South Boston is an incredibly tight-knit community, one that always prefers to keep things internal rather than handing them off to outsiders. As we'll see, this bites them in the butt in a major way.

Yeesh—now that's dark. Although Connolly has worked elsewhere as an FBI agent, taking one notable stint in the Big Apple, he always knew he'd end up back in South Boston—his home. But is that really a good thing? What do you think?

This central tenet of the Southie community–"never trust outsiders"—becomes a rallying cry for Bulger and Connolly as they unleash their decades-long reign of terror on Boston. The irony is too much to bear.

To Connolly, Whitey Bulger represents South Boston. Scratch that: Whitey is South Boston. Given this heavy symbolic association, it's no wonder why Connolly fights so fiercely for Bulger. He sees any attack on Whitey as an attack on his community of South Boston. Wow. Freud would've had a field day with this guy.

Bulger's relationship with the Southie community has two sides. On one hand, he clearly loves South Boston and its people. On the other, he causes a lot of irreparable damage to their lives. It's almost like he's two different people.

Remember what we said about not trusting outsiders? In a brilliant rhetorical move, Connolly frames any criticism of Whitey as a Trojan Horse to destroy South Boston from the inside. Impressive. That's reaching Alex Jones levels of conspiracy insanity.

Flemmi sees two reasons why Connolly and Whitey become so close. First is the reason we've been discussing the whole time: Connolly and Bulger are both Southie boys at heart. But there's something deeper here than just shared community ties. In many ways, Connolly views Bulger as a role model. Bad pick, buddy.

Once again, we see that misguided belief that Bulger is some sort of secret benefactor for Southie. Kind of like Batman, only if instead of solving crimes Batman committed them. So, uh, not like Batman at all. More like the Joker?

Both Bulger boys—Whitey the crime boss and Billy the politician—are central figures in South Boston, and both are protected by the FBI when they land in hot water. This allows them to retain control of Southie despite the truth of their misdeeds coming to the surface.

Ouch—did Connolly tell Whitey he wasn't his favorite Bulger? That would've broken the poor guy's heart. And when Whitey's heart gets broken, well, then the heartbreaker's bones usually meet the same fate.