Character Analysis
No one can exploit FBI protocol with quite the same panache as agent John Connolly.
The man single-handedly responsible with bringing Whitey Bulger into the fold in 1975, Connolly loves the cred he gets for managing the Boston department's star informant, no matter how much shady stuff he does along the way.
South Side Represent
One big thing to remember about John Connolly is that he's a Southie: a native of South Boston. In fact, "he'd grown up in the brick tenement near the Bulgers' in the Old Harbor housing project in South Boston" (1.1.8).
These deep roots not only help Connolly navigate the highly politicized world of the Boston FBI, but also to strike a unique connection with the notorious gangster. These two are old friends from the hood—of course they're going to be buddy-buddy.
And boy does Whitey exploit their relationship for everything it's worth…though to be fair Connolly is an eager participant. Sometimes, he fudges paperwork to make Bulger seem more useful than he actually is. Other times, he leaks intel to help him dodge the fuzz. He even goes to bat for Bulger within the FBI, fighting off naysayers like a Jedi slicing through Stormtroopers.
Er—or maybe a Sith?
Star Turn
At first, this works beautifully. Bulger gets the protection of the FBI; Connolly gets to strut around like big man on campus. He begins "to operate like a salesman—skilled at feigning sincerity but uninterested in the real thing" (1.4.46). He also takes a shine to the media spotlight, hamming it up for reporters like he's pitching a reality TV show.
By the 1990s, Connolly has sold his soul to Bulger—and at a steal. For example, he leaks info to the gangster about an informant named Brian Halloran, which Bulger uses to murder the poor guy. Similarly, Connolly continues to protect Bulger even after it's proven that he's responsible with flooding South Boston—their shared home—with crack cocaine. Skeezy.
Big Bark, Small Bite
Connolly remains as flashy as ever even after his ties with Bulger are revealed in court. Staying true to his self-image as a master of media, he goes on countless news station to defend himself in absurd fashion.
Check it out:
Connolly was saying, immunity be damned—he didn't want it, he didn't need it. "I do not need immunity for corrupt acts," he told the Boston Tab. "I did not commit corrupt acts. I would refuse immunity for those reasons. I don't need it." (3.20.106)
But when he's actually brought to court, his tough guy shtick is conspicuously missing. Instead, Connolly invokes his Fifth Amendment rights—the right to not incriminate himself—to every question asked by the prosecution, however minor. That sure makes him seem believable.
Finally, in 2005, Connolly is convicted as an accessory to several of Bulger's murders, and is sentenced to forty years behind bars—a life sentence for a guy his age. While Whitey himself won't be captured for another six years, we're sure his childhood buddy will be keeping a cot warm for him.