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.

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.

The Bulger brothers become so powerful that they define South Boston. Billy protects Southie in the senate; Whitey protects Southie in the streets. Of course, this isn't entirely accurate, but it becomes a key piece of neighborhood's DNA.

After a while, the rest of the government—most notably the DEA and Massachusetts state police—gets wise to the buddy-buddy relationship between Bulger and the FBI. They don't know the full story, but they know that some dirty business is happening behind the scenes.

He might be utterly devoid of morals, but Whitey sure is ambitious. And punctual. Jokes aside, this is a huge early warning sign that Bulger is going to be trouble, but Connolly doesn't even skip a beat. Not a good look for an FBI agent.