How we cite our quotes: (Part.Chapter.Paragraph)
Quote #1
In May 1972 [...] even though he was Killeen's bodyguard, Bulger entered into a secret alliance with his enemies. (1.2.34)
Even before he becomes an informant, Bulger is already working all the angles to his own benefit. No wonder John Connolly is no match for him—it's like Conor McGregor having a boxing match with Conan O'Brien.
Quote #2
Like a chessmaster, Bulger was confident that he knew the moves, that he could watch your opening and lead you straight to checkmate. (1.2.42)
Bulger is a deeply strategic thinker, so from the moment he makes a deal with the FBI he's already thinking about how he can exploit it for his own benefit. And boy does he. Thanks to the help of FBI agent John Connolly, he grows from being a run-of-the-mill hitman to legit boss.
Quote #3
Connolly not only occasionally talked to reporters but also regularly courted them. (1.3.35)
The more time he spends canoodling with gangsters, the more Connolly starts acting like one himself. It's almost as if Whitey Bulger is rubbing off on the FBI agent.
Quote #4
Bulger especially was proving to be the grand puppeteer, pulling the strings of both the FBI and La Cosa Nostra. (1.5.84)
Bulger isn't just working the FBI—he's also working the Mafia. By playing both sides against each other—all while under the personal protection of Connolly—Bulger is able to build an insane criminal empire without breaking a sweat.
Quote #5
But Connolly was exerting his influence over Morris more than ever before, his bombastic personality overwhelming the introverted boss. (2.7.7)
John Morris is brought into the Organized Crime Squad to chill out the increasingly erratic Connolly, but the supervisor quickly gets in over his head. Even worse—he becomes an active participant in Connolly and Bulger's schemes. And that's another point for Bulger.
Quote #6
Morris and Connolly may have once thought they were in control of the relationship, but they and the FBI were now just intoxicated passengers. (2.8.56)
At some point, everything flips, and Bulger takes the upper hand in his relationship with the FBI. Maybe it's because they've covered up so many of his crimes. Maybe it's because they've offered them protection. Maybe it's that they've literally let him into their home. Either way, things are about to take a turn for the worse, if you can believe it.
Quote #7
Many of the FBI documents about Bulger were simply invention—and at this Connolly became the master. (2.9.33)
Connolly might not be a good FBI agent, but he's a pro at forging documents. He's, like, the Michael Jordan of subverting the truth and exploiting loopholes in regulations. Hooray?
Quote #8
They had Morris in their grip, and he'd come cheap—a plane ticket for an illicit tryst. (2.9.24)
Morris resists for a while, but he eventually gives in and starts taking straight cash from Bulger and the gang. This is his personal Rubicon: he can never go back to being a normal FBI agent now.
Quote #9
"He couldn't write a report. He was no administrator. He was just this brassy bulls*** artist." (2.10.56)
It turns out that Connolly isn't even an effective FBI agent: he's just good at pretending to be one. Sadly, this does little to slow his ascent within the bureau.
Quote #10
The technique benefited Bulger, for between the two, Flemmi was the one with long personal ties to the Mafia. Flemmi, not Bulger, had the juice. (2.15.43)
The most hilarious thing about the whole situation is that Flemmi is actually a decent informant—Bulger's the dead weight. If the FBI had just brought Flemmi onboard and called it a day, they would have saved themselves a lot of headaches—not to mention corruption hearings.