Green was the first big bend in the Whitey Bulger highway [...] Connolly quickly set out to ensure that the case would never leave the Organized Crime Squad. (1.3.18)
Although the deal with Bulger is shady from the onset, it's not until Bulger is accused of shaking down a local restaurant owner that laws really start getting broken. Connolly then implements a system he'll use time and time again when Bulger gets in trouble: stick his hands in his ears and say, "Nyah, nyah, nyah." More or less.
Rico had fashioned a "unique" style in his approach to the messy business of managing informants and had set the tone for other handlers in Boston: rules were made to be broken. (1.4.1)
Even before Connolly starts working for the Boston FBI, Agent Paul Rico makes corruption the law of the land for the Organized Crime Squad. In fact, Rico protects Steve Flemmi the same way that Connolly later protects Whitey Bulger. The dude literally writes the playbook on how to inappropriately manage informants. The anti-rulebook, if you will.
None of the information obtained during these warrantless break-ins and bug installations could be used [...] in court, but the bugs provided a windfall of intelligence. (1.4.23)
The Organized Crime Squad isn't the only branch of the FBI that plays fast and loose with the rules. Whether breaking into gangsters' homes, threatening them with violence, or employing illegal methods of surveillance, the FBI seems to embody the idea that "the ends justify the means." They just don't expect anyone to take it as far as Connolly does.
[T]he dramatic language used to cheer on agents regarding informants borders on the breathless. (1.4.14)
Part of the blame for the Bulger debacle belongs with the FBI itself. The bureau places such a strong emphasis on managing informants that some shady stuff is bound to happen.
Looking around the office at [...] the flashy Connolly [...] Morris was like the team manager jealous of the jocks who started had starred in the big game. (1.5.21)
Although John Morris is specifically chosen to be the supervisor of the Organized Crime Squad due to his fastidious devotion to the rules, it doesn't take much for that devotion to fall by the wayside. After all, Connolly is breaking all the rules, and he seems to be getting along just fine. Why shouldn't Morris get in on the action?
Morris admitted later that the foray was helpful by not necessary to get court approval for the bug. But [...] Bulger and Flemmi made it into the massive T3 document. (2.7.28)
One of the less flashy ways Connolly manipulates the FBI into thinking that Bulger and Flemmi are more important than they actually are is by including their claims, however tangential, in major cases. This way Connolly can build up himself and his informants without actually breaking any rules. Convenient.
Morris had stumbled out of the hotel, leaving behind the top-secret government tape recording he had so proudly played for Bulger and Flemmi. (2.8.55)
Look how far the rule-abiding John Morris has fallen. He gets so drunk partying with Bulger and Flemmi that he leaves a confidential FBI recording in the hotel, which oh by the way he was just playing for these two criminals. Wow. Didn't take too long, huh?
John Morris was now the supervisor of a white-collar squad that mainly pursued public corruption. (2.15.60)
In the end, this is Morris and Connolly's legacy: "public corruption." No matter their intention at the onset, their enabling of Bulger has caused untold pain and suffering, which they in turn profited from.
The deal [...] was by now so out of whack that any good [...] was offset by a wave of concessions and corruption. (2.15.46)
By now, Connolly and Morris have broken so many rules that the FBI needs to cover for them just to save its own neck. There would be a massive public outcry if this tomfoolery were made public.
During the private debriefings with FBI agents and prosecutors that accompanied those negotiations, [Morris] wept. (3.20.32)
Morris knows that he's done awful stuff and is rightfully ashamed. That's not much to write home about, but it's a lot better than Connolly, who pleads the Fifth in court so many times that his tongue probably has blisters. That guy can't say remorse, much less have it.