Whitey Bulger—who, we want to remind you, is a real person—is a once-in-a-generation gangster. The kind of G they write hip-hop street ballads about. The kind of G whose life is so insane it inspires a series of epic crime movies.
Well, one down in that department.
But this tough guy had a dirty little secret: he was an informant for the FBI starting way back in 1975. Oops. In fact, Bulger likely would never have reached such heights in the criminal underworld without the support of his corrupt crew of FBI cronies.
For John Connolly, the FBI agent who brought Whitey onboard, Bulger is the epitome ofhis native neighborhood of South Boston, better known as Southie. The two grew up together on Southie's mean streets, where Whitey embodied the hood's hardscrabble, take-no-prisoners attitude. In many ways, as law enforcement officer and criminal, the two men "came together as book ends on the narrow spectrum of careers available to Irish Catholics" from Southie (1.2.5).
There's one big thing that sets Bulger apart from Connolly, however: Bulger is a brilliant strategic mind. Whitey sees himself as a "chessmaster" who's so "confident that he knew the moves, that he could watch your opening and lead you straight to checkmate" (1.2.42). In fact, Bulger only became such an intense planner after his early stints in prison, when he decided he'd do whatever it took to stay free.
Besides give up crime, of course.
Don't think Whitey used the FBI merely for protection. Far from it: they were his Swiss army knife of corruption, capable of helping out in countless sticky situations.
The DEA's closing in on one of Bulger's operations? Whitey knows ahead of time. A new crew kicking around Southie? Connolly's the hook-up for inside info. An informant looking to make trouble for Bulger? No problem. He'll cap the fool thanks to the help of his friendly neighborhood FBI agent.
If you can't tell, we're referencing Brian Halloran with that last one, an informant Bulger murders thanks to a tip-off from Connolly, by way of John Morris. This is big turning point. The FBI had long known that Connolly was involved in shady business with Bulger, but:
[…] it was Brian Halloran's dead body on Northern Avenue that left a deep mark on agents in the Boston office. (2.10.60)
These agents can't turn a blind eye to Bulger's brutality like they had before.
Another turning point came when Bulger dipped his toes in the drug business. Although Whitey is anti-drug on a personal level, he profitted from every single ounce of dope sold in South Boston through "rents" he charged local drug dealers. No matter how much he claims to be some sort of good-hearted anti-hero, the truth is that "Southie had suffered in Whitey's hands" (2.12.21).
This gets at a deep truth about Whitey Bulger: he doesn't see himself as a bad guy. Check out this iconic interaction with the DEA:
"Hey," announced Bulger at one point to the DEA agents, "we're all good guys."
"You're the good good guys. We're the bad good guys." (2.12.88-90)
In other words, Bulger sees himself as an anti-hero, not a villain. Yeah, buddy, and so is Voldemort.
Still, Bulger managed to convince the entire city of Southie that he was a nice guy for decades. No matter how lives he destroyed, how many businesses he stole, or how many people he murdered, he still managed to maintain a pristine reputation. Quite a bit of PR jujitsu.
It wasn't until the full extent of Whitey's misdeeds—and his status as an informant—was revealed in the 1990s that the hood realized how badly it'd been bamboozled.
In a move that only he could pull off, Bulger evaded the police for almost two decades with his girlfriend Catherine Greig. And the dude was over seventy at this point. He must have been drinking his prune juice.
But the good times couldn't last forever, and the FBI eventually caught up with him in the most hilarious possible: they received a tip about Greig feeding local strays in their new California neighborhood. Drat on you, felines. Foiled once again.
Thanks to our purr-fect friends, Whitey Bulger would finally pay for his crimes. It might have been roughly three decades behind schedule, but some things are better late than never.