Character Analysis
In comparison to the brutal Whitey Bulger, Steve Flemmi seems almost sympathetic at times.
And then you remember that his nickname is "The Rifleman" on account of his most excellent killing skills, which he frequently uses to murder innocent people.
So, uh, maybe not so sympathetic after all.
Better than Bulger
Still, there's some justification for liking Flemmi better than Bulger. First off, he's actually an effective informant. "Flemmi was the one with long personal ties to the Mafia" and consequently "had the juice," so to speak (2.15.43) Had Flemmi been the only informant in the FBI's arsenal, things would've never gotten so insane.
Flemmi is also nowhere near as brilliant or conniving as Bulger, which makes him seem like a lovable buffoon at times. For example, in the early '90s, as Bulger is putting the finishing touches on his criminal empire, Flemmi is flying around the world and skydiving in exotic locales. The dude is enjoying retirement in style.
Flemmi the Flustered
Plus, the poor guy doesn't entirely understand the deal he's made with the FBI, if his testimony in court is any indication. Check out this hilarious, tongue-tying exchange with federal prosecutor Fred Wyshak, for instance:
FLEMMI: Excuse me, Mr. Wyshak. I just wanted to clarify one thing, when you asked me a question about did I know he was breaking the law. As far as I'm concerned, everything he was doing was legal—illegal—excuse me, legal. (3.20.77)
Wow. Flemmi gets so twisted up it's almost impressive. From the moment he makes a deal with the FBI, Bulger is already planning how to exploit it to his benefit. Flemmi, on the other hand, is just along for the ride.
Whatcha Gonna Do When They Come for You?
Don't let this make Flemmi seem like a nice fellow. He's still "The Rifleman" after all. He commits crimes as horrendous as anything on Bulger's rap sheet, such as the murder of his side girlfriend Deborah Hussey, who oh, by the way is the daughter of his main girlfriend. Ew.
So, while he might not be a criminal mastermind to the degree of Bulger, Flemmi is still one scummy guy.
In true Flemmi fashion, the aged gangster is only arrested after being indicted in 1995 because he returns to Southie despite Connolly's warning. If he had one lick of sense, he would've stayed away like Bulger and gained himself a few extra decades as a free man. Then again, there's a reason they call him "The Rifleman" and not "The Rocket Scientist."