How we cite our quotes: (Part.Chapter.Paragraph)
Quote #1
Connolly's proposal was simple: inform on La Cosa Nostra and let the FBI do the rest. (1.1.26)
In his quest to take down the Mafia, Connolly turns to Bulger, hoping that the gangster can help him infiltrate the tight-lipped organization. In the immortal words of Gob Bluth: he's made a huge mistake.
Quote #2
Dennis Condon and Paul Rico were among the handful of agents picked to staff the city's first-ever Organized Crime Squad. (1.4.5)
In horrendously ironic fashion, the very agents chosen to take down the Mafia end up fostering corruption within the FBI. Funny how things pan out. Paul Rico in particular is the big granddaddy of them all: he brings Flemmi on as an informant and covers for him when he gets in hot water.
Quote #3
Bulger was making his move upward as a crime boss in his own right. (1.5.85)
In the least surprising development ever, Bulger starts rising the criminal ladder as soon as he develops a relationship with the FBI. Who could've guessed that…except everyone.
Quote #4
But there were the new rumors, especially after the race-fixing indictments when Bulger had eluded prosecution. (2.6.37)
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.
Quote #5
Crossing Morris's desk for the first time was information about Bulger grabbing a piece of the action in cocaine. (2.9.31)
Although Whitey claims to be anti-drug, he's single-handedly responsible for flooding South Boston, his hometown, with crack cocaine. Whitey loves to act like he's some edgy anti-hero, but he's really just a greedy crook.
Quote #6
[T]he gangsters had shaken the troopers tailing them by finding safe haven [...] in the homes of FBI agents. (2.9.50)
At a certain point, the FBI goes from turning a blind eye to Bulger's crimes to actively helping him get away with them. In other words, these suit-wearing FBI agents have become criminals themselves.
Quote #7
He'd make the world safe for drug dealers in return for a piece of the action, but he didn't personally cut the coke or bag the marijuana. (2.12.25)
Despite his criminal activity, Bulger somehow maintains a solid reputation in Southie. He's not just any old gangster—he's their gangsters. He only exploits outsiders—not Southies. Of course, we know the sad truth: no one has inflicted more damage on Southie than Bulger.
Quote #8
"Hey, announced Bulger at one point to the DEA agents, "we're all good guys."
How so?
"You're the good good guys. We're the bad good guys." (2.12.88-90)
In Bulger's head, he's Han Solo—the good guy who doesn't play by the rules—when in fact he's straight-up Darth Vader. He's the villain. Despite its obvious absurdity, this twisted moral justification fuels Bulger's criminal activity throughout his career.
Quote #9
The defense attorneys [...] were portraying Flemmi as if he were "Junior G-man with a license to kill."
"Isn't that preposterous?" mocked Wyshak. (3.20.11)
It might be preposterous, but it's a fairly accurate depiction of the twisted relationship Flemmi and Bulger develop with the FBI. Connolly and Morris have turned a blind eye to crime after crime—and murder after murder. Why shouldn't Flemmi believe that he has a license to kill? He certainly hasn't been treated like your average murderer.
Quote #10
Flemmi got mixed up [...] about whether he was supposed to view the leaks he'd gotten from FBI agents as either legal or illegal acts. (3.20.72)
Flemmi has no idea which way is which. Is he the informant? Or is he the FBI agent? It's hard to blame him for his confusion, however. By now, he's been living inside his FBI-maintained bubble for decades, so he hardly remembers what it's like to be an average, accused criminal.