Study Guide

Black Mass: Whitey Bulger, the FBI, and a Devil's Deal Quotes

By Dick Lehr and Gerard O'Neill

  • Community

    Chapter 1—Part I

    Connolly was surely thinking about [...] where he had come from. A circle, a loop, the shape of a noose—all road led to Southie. (1.1.59)

    Yeesh—now that's dark. Although Connolly has worked elsewhere as an FBI agent, taking one notable stint in the Big Apple, he always knew he'd end up back in South Boston—his home. But is that really a good thing? What do you think?

    Chapter 2

    The shared battles reaffirmed a view of life: never trust outsiders and never forget where you come from. (1.2.5)

    This central tenet of the Southie community–"never trust outsiders"—becomes a rallying cry for Bulger and Connolly as they unleash their decades-long reign of terror on Boston. The irony is too much to bear.

    Connolly would always stay a poor city kid looking for acceptance in a hardscrabble world, permanently susceptible to the macho mystique of Whitey Bulger. (1.2.25)

    To Connolly, Whitey Bulger represents South Boston. Scratch that: Whitey is South Boston. Given this heavy symbolic association, it's no wonder why Connolly fights so fiercely for Bulger. He sees any attack on Whitey as an attack on his community of South Boston. Wow. Freud would've had a field day with this guy.

    Chapter 6—Part II

    They realized that Bulger's demeanor seemed to soften in South Boston, away from Lancaster Street. (2.6.31)

    Bulger's relationship with the Southie community has two sides. On one hand, he clearly loves South Boston and its people. On the other, he causes a lot of irreparable damage to their lives. It's almost like he's two different people.

    Chapter 7

    Connolly's internal memo said that Bulger viewed the state police as part of a conspiracy to embarrass his brother Billy. (2.7.21)

    Remember what we said about not trusting outsiders? In a brilliant rhetorical move, Connolly frames any criticism of Whitey as a Trojan Horse to destroy South Boston from the inside. Impressive. That's reaching Alex Jones levels of conspiracy insanity.

    Chapter 9

    Flemmi saw that there was something special between Connolly and Whitey Bulger. It was South Boston, for sure, and maybe part of it was a father-son thing. (2.9.2)

    Flemmi sees two reasons why Connolly and Whitey become so close. First is the reason we've been discussing the whole time: Connolly and Bulger are both Southie boys at heart. But there's something deeper here than just shared community ties. In many ways, Connolly views Bulger as a role model. Bad pick, buddy.

    Chapter 11

    It was often spread around town that Bulger was supremely loyal to the people of Southie, that he liked helping people. (2.11.55)

    Once again, we see that misguided belief that Bulger is some sort of secret benefactor for Southie. Kind of like Batman, only if instead of solving crimes Batman committed them. So, uh, not like Batman at all. More like the Joker?

    Chapter 14, Part II

    And just as the FBI had protected Whitey Bulger for fifteen years, the bureau stepped in to keep William Bulger out of harm's way. (2.14.21)

    Both Bulger boys—Whitey the crime boss and Billy the politician—are central figures in South Boston, and both are protected by the FBI when they land in hot water. This allows them to retain control of Southie despite the truth of their misdeeds coming to the surface.

    Connolly now swooped in to run interference for brother Bill—his real hometown hero. (2.14.29)

    Ouch—did Connolly tell Whitey he wasn't his favorite Bulger? That would've broken the poor guy's heart. And when Whitey's heart gets broken, well, then the heartbreaker's bones usually meet the same fate.

    Connolly brought something to the table no one else could: [...] he'd grown up in the brick tenement near the Bulgers' in the Old Harbor housing project in South Boston. (1.1.8)

    Here's one big reason why Bulger and Connolly hook up: they were practically next-door neighbors growing up. It also helps that South Boston is an incredibly tight-knit community, one that always prefers to keep things internal rather than handing them off to outsiders. As we'll see, this bites them in the butt in a major way.

  • Criminality

    Chapter 1—Part I

    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.

    Chapter 4

    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.

    Chapter 5

    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.

    Chapter 6—Part II

    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.

    Chapter 9

    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.

    [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.

    Chapter 12

    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.

    James "Whitey" Bulger

    "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.

    Chapter 20
    Steve "The Rifleman" Flemmi

    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.

    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.

  • Visions of Southie

    Chapter 1—Part I

    In 1974 a federal court order to bus black students from Roxbury to South Boston High School [...] had turned the neighborhood into a war zone. (1.1.15)

    This is our introduction to Southie and, well, it doesn't exactly fill us with good feels. According to Black Mass, however, residents are only freaking out because the feds are forcing integration on the city. There might be some truth to that, but given Southie natives' feelings towards outsiders, that can't be the whole story.

    Chapter 2

    Over the decades since then, nothing has galvanized Southies more than a perceived slight by an outsider who would change The Way Things Are. (1.2.11)

    There's only one thing Southies hates more than an outsider: an outsider who wants to change Southie. The nerve. This points to a deep conservative streak that runs through South Boston, one that is perhaps best embodied by Billy Bulger himself.

    They came together as book ends on the narrow spectrum of careers available to Irish Catholics [...] on the spit of land jutting into the Atlantic Ocean. (1.2.5)

    For residents of South Boston of Connolly and Bulger's generation, there aren't many opportunities to move up the social ladder. You could either become a cop or a criminal, and even then there's no guarantee you'd make a decent living. No wonder why Connolly and Bulger are so power-hungry.

    Beyond common ethnic roots, the magnet of daily life was the Catholic Church. (1.2.14)

    Given Southie's heavy Irish-American population, it only makes sense that it's a stronghold for the Catholic Church. Southie's conservative streak once again rears its head.

    To this day the neighborhood consistently maintains the highest percentage of long-term residents in the city. (1.2.9)

    These days, pretty much everyone wants to leave their hometown as soon as they reach twenty, so it's notable that residents of South Boston tend to stick around. This makes the community even more tightknit than it would be otherwise.

    Chapter 6—Part II

    1980 was a time when both Bulgers were consolidating their power and fast approaching the top of their games. (2.6.11)

    The Bulger brothers become so powerful that they define South Boston. Billy protects Southie in the senate; Whitey protects Southie in the streets. Of course, this isn't entirely accurate, but it becomes a key piece of neighborhood's DNA.

    Chapter 12

    Whitey might rarely be seen, but his presence was palpable and, for many, a source of comfort [...] He had the right touch that way—sticking to the shadows. (2.12.22)

    Whitey knows that he's inflicted damage on Southie, but he's exceptionally skilled at covering his tracks. He also makes it a point to lend help to the residents of Southie when they least expect it, thereby keeping them hooked on him like a drug—sort of like the drugs that have decimated the neighborhood, brought in by Bulger himself.

    Southie had suffered in Whitey's hands. This was the reality that Bergeron knew, that DEA agents knew, that state troopers knew, that drug dealers all around knew. (2.12.21)

    Despite the widespread stories of Whitey doing good for the people of Southie, the sad truth is that he's inflicted untold damage on the city he claims to love. He's murdered its residents. He's extorted its businesses. He's flooded the streets with drugs, creating hordes of addicts overnight. So Whitey is no hero to Southie at all—he's its villain.

    Chapter 15
    James "Whitey" Bulger

    "I'm from South Boston, shrugged one of the witnesses, trying to explain the turnabout to the judge. "We keep things to ourselves." (2.15.50)

    So how does Whitey's reign of terror last so long? Remember, Southie is defined by its opposition to outsiders. For a Southie, Whitey is one of them, while the FBI, DEA, and Justice Department are just another group of feds trying to change the Southie way of life.

    Whitey Bulger had stayed on in the family apartment on O'Callaghan Way in the South Boston housing project. (2.6.9)

    Remember how we said that residents of Southie tend to stick around? Whitey Bulger is no exception. The fact that Whitey sticks so close to his roots would almost be admirable if he wasn't, you know, a mass murderer.

  • Manipulation

    Chapter 2

    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.

    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.

    Chapter 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.

    Chapter 5

    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.

    Chapter 7

    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.

    Chapter 8

    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.

    Chapter 9

    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?

    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.

    Chapter 10
    John Connolly

    "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.

    Chapter 15

    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.

  • Violence

    Chapter 2
    James "Whitey" Bulger

    The fast, bloody "Godfather" takeover [...] would be [...] a formal notice to the underworld that Bulger was soon to manipulate and control. (1.2.39)

    Make no mistake—Bulger isn't some sympathetic criminal who only turns to illegal activity to save his dying wife, or [insert sob story here]. He's a criminal because he loves it. He beats people up because it's fun. No wonder he rises to the rank of mob boss in record time.

    "He wasn't a bully, but he was looking for trouble. You could sense him hoping someone would start something." (1.2.28)

    Although Bulger wasn't a particularly cruel kid, he was certainly known to throw hands from time to time. Of course, as we'll see, adult Bulger seems to get a disturbing amount of joy from inflicting pain on other people.

    Chapter 3

    It didn't matter that two prosecutors were seated across the way. Bulger leaned into Green's face, [...] "If you don't pay, I will absolutely kill you." (1.3.8)

    Bulger has so much chutzpah that he'd rob a bank that was across the street from a police station. On the other hand, he might only act so tough because he knows that the FBI has his back. It's easy to be a rough rider when you have federal agents as wingmen.

    Chapter 6—Part II

    [J]ust five weeks after the Whitey Bulger informant file was [...] opened [...] Whitey chalked up his first murder while on FBI time. (1.6.63)

    He might be utterly devoid of morals, but Whitey sure is ambitious. And punctual. Jokes aside, this is a huge early warning sign that Bulger is going to be trouble, but Connolly doesn't even skip a beat. Not a good look for an FBI agent.

    Chapter 9

    They'd fallen completely off the game board [...] now criminals all, FBI agents and two gangsters looking to deflect trouble of any kind, including charges of murder. (2.9.76)

    Connolly and Morris may have come in with noble intentions, but as the years pass their deal with Bulger becomes increasingly corrupt. In fact, there are multiple instance when they leak intel to Bulger that he uses to kill people. That's well beyond fudging reports or inflating your informant's credibility. That's being an accessory to murder.

    Chapter 10

    There'd been a number of housekeeping murder of minor figures [...] but the growing body count brought not a single knock on Bulger's door. (2.10.9)

    As time rolls on, Connolly and Morris become a well-oiled cover-up machine, successfully derailing any investigation into Bulger's violent crimes. This only makes Whitey more confident, culminating in his assassination of an Arizonan multimillionaire for screwing up a business deal.

    In the aftermath Weeks found Bulger "euphoric" and unable to talk about anything else for days. (2.10.51)

    The fact that Bulger enters a state of bliss after brutally murdering Brian Halloran settles the debate once and for all. Bulger doesn't just use violence—he loves it. He's a legit monster.

    Chapter 13
    John Morris

    Morris, his wine nearby but clearly sober, said, "You can do anything you want as long as you don't clip anyone." (2.13.43)

    Yeah, we're sure asking him nicely will work great, Morris. Seems to have turned out swell the past few decades. By now, Bulger has taken the driver's seat in their relationship, and he's not handing back the wheel anytime soon.

    Chapter 15
    John Connolly

    Connolly was unmoved. "But he's a good guy." Besides, he said, the dead man was "a piece of s***." (2.15.55)

    Although Connolly isn't referring to Bulger here, this might help us understand how he so casually helps Bulger murder several men. Moral superiority is one heck of a drug.

    James "Whitey" Bulger

    Forget the "good bad guy" myth. Bulger, said Stearn, was "a serial killer." (e.27)

    The revelation of Bulger's crimes causes an explosion the likes of which is rarely seen outside of a Michael Bay movie. And for good reason. Bulger has for too long hid behind his image as an anti-hero. It's time for Southie to see his true colors.

  • Power

    Chapter 2

    At once [Billy] was a petty despot and a masterful conciliator, [...] a puckish public performer who had a dark side and took all slights personally. (1.2.21)

    Whitey isn't the only bigwig Bulger bossing it up in Boston—there's also brother Billy, state senator and grouch extraordinaire. Despite being more "legit" than his big bro, Billy is just as willing to throw his weight around to get what he wants. They call that Bulger style.

    Chapter 5

    Like a drug, their ties to Bulger and Flemmi had evolved into a dependency that was hardening quickly into an addiction. (1.5.89)

    The FBI's relationship with Bulger and Flemmi certainly has its benefits. It gives the FBI a leg up in the mob, and Flemmi's intel helps them break several major cases. But there's a downside: the longer they're together, the more Bulger dominates the relationship.

    Chapter 6—Part II

    1980 was a time when both Bulgers were consolidating their power and fast approaching the top of their games. (2.6.11)

    As the decades chug along, the Bulger boys only gain more power for themselves: Billy in the state senate, and Whitey in the mean streets of Southie. In fact, both men become so powerful that they become inescapably linked to South Boston itself.

    Chapter 8

    [B]oth sides knew that the wary collaboration between Bulger and the Mafia was the cornerstone of organized crime in Boston. (2.8.49)

    The irony of all ironies is that Whitey isn't only getting help from the FBI: he's also getting help from the Mafia, which he's also helping the FBI destroy. He's not just playing both sides like a fiddle—he's conducting a legit orchestra.

    Chapter 10

    Roger Wheeler may have been a multimillionaire [...] but [...] Wheeler was just another guy in Whitey Bulger's way. (2.10.11)

    The assassination of Roger Wheeler is Bulger's boldest move ever. He's killed plenty of people already, but none were as prominent or as well-connected as Wheeler. It just goes to show how powerful this project-born ex-con has become.

    Chapter 20

    By this time John Connolly had emerged as the kind of quintessential public figure for the 1990's, a decade increasingly obsessed with style and celebrity. (3.20.108)

    Whitey isn't the only one gaining steam: Connolly's making major moves himself, emerging as a minor celebrity. Okay, okay, so he might not break C-tier, but that's pretty impressive for an FBI agent. And you can believe that Connolly is going to milk his 15 minutes for everything they're worth.


    He was sentenced to forty years in prison [...] all the bluster had gone out of the Connolly balloon. (e.51)

    And then, just like that, it's all gone. All that bravado, all that swagger, all that bullying and macho posturing—gone in an instant. A lifetime sentence in federal prison will do that to a guy.

    For the first time eve Whitey Bulger's younger brothers began to pay a price [...] for their boundless loyalty to the crime boss and killer. (e.60)

    The Bulger brothers were more than willing to use Whitey to their own benefit, so it's only fair that they're knocked down a peg when his corruption is revealed. Given the Bulgers' prominence in South Boston, this is a massive scandal in the community.

    John Connolly

    Connolly, properly obsequious to a neighborhood elder who was also an icon, made his offer: "You should think about using your friends in law enforcement." (1.1.11)

    Does this seem like the right way for an FBI agent to deal with a known gangster? Does being a "friend" to a crime lord count as a justified use of federal power? If you answered "yes" to either one of these questions, then you might be John Connolly. Hiya John.

    They saw only what they wanted to see. It was a moment built on a shared premise: the future belonged to them. (1.5.90)

    Bulger, Flemmi, Connolly, and Morris create their own little slapdash gang, distinct from both the FBI and the criminal underworld. Their goal? Make sure that each of them becomes as powerful as possible. Where do we sign up?

  • Rules and Order

    Chapter 3

    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.

    Chapter 4

    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.

    Chapter 5

    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?

    Chapter 7

    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.

    Chapter 8

    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?

    Chapter 15

    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.

    Chapter 20

    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.

  • Justice and Judgment

    Chapter 4

    The Racketeering Influenced and Corrupt Organizations Act, known simply as RICO, would be used in nearly every major prosecution against the Mafia during the 1980's. (1.4.9)

    During the '60s and '70s, the FBI makes taking down the Mafia their number one priority. RICO is a big part of that: It allows them to put pretty much any national-level crime boss in prison for a long time. That's a useful tool when you're up against such a finely-tuned and tight-knit criminal organization as La Cosa Nostra (another term for the Mafia).

    Chapter 5

    Connolly said later that O'Sullivan's intervention provided a new layer of protective veneer to the FBI's deal. (1.5.82)

    Bulger is signed on as an informant to help bring the Mafia to justice, but he ends up sparking quite a bit of injustice himself. What's more, he reveals many FBI agents, like Connolly, Morris, and O'Sullivan, to be more concerned with good press than actually doing the right thing.

    Chapter 8

    From the beginning the agents did the best they could to cover up for Bulger and Flemmi as their misdeeds tumbled off the tapes in 1981. (2.8.33)

    Connolly is so convinced that Bulger and Flemmi will help the FBI take down the Mafia that he's willing to do whatever it takes to keep them out of jail. Theft? No biggie. Racketeering? Chump change. Assault and murder? Not Connolly's problem. A real moral stalwart, right here.

    Chapter 10

    It was Brian Halloran's dead body on Northern Avenue that left a deep mark on agents in the Boston office. (2.10.60)

    Halloran is a prospective informant against Bulger who's murdered after Connolly leaks his identity to crime boss. Shady. By now, the rest of the FBI has no illusions: the deal with Bulger is causing more evil than it's stopping.

    Chapter 12

    [T]he moment Bulger had uttered the line, "He's right—there is a bug in the car," DEA agent Reilly was convinced that the FBI had tipped of Bulger. (2.12.97)

    No matter how expertly they plan their raids, the DEA remains one step behind Bulger. This just confirms their suspicions: Connolly is definitely leaking intel to the gangster. That's got to be against the bro code. Even if they now know that Connolly is their enemy, however, they still don't know how to take him down.

    Chapter 16
    John Morris

    "I think part of it, if Connolly were surfaced, that would mean that I would be surfaced; and I think at that point in time I in fact wanted my own involvement surfaced." (2.16.18)

    John Morris has always had reservations about the deal with Bulger—though to be fair, those reservations weren't enough to stop him from accepting thousands of dollars in bribes. No matter the reason behind his sudden admission to the Boston Globe, however, it kicks off the chain of events that finally lands Whitey where he belongs: a jail cell.

    Chapter 18

    Flemmi was like a Hollywood celebrity arrested for drunken driving. Protests about his importance would only make things worse. (3.18.49)

    Not to be cruel, but Flemmi's inability to realize that he's going to jail is hilarious. He's been let off the hook so many times that he can't process that he's finally being brought to justice for his crimes. Hey—they call him "The Rifleman," not "The Brainiac." There's a reason for that.

    Chapter 20

    More than half of the text—365 pages—was devoted to factual findings about all that had gone wrong in the FBI's deal with Bulger. (3.20.153)

    Wow—that means that Judge Wolf's ruling is almost as long as Moby Dick. Not exactly easy reading. Also, keep in mind that Bulger isn't even the defendant in this case: his informant kerfuffle is a mere sideshow. But no one can deny that it's one juicy piece of gossip.

    But even a renewed attack could not remove the lasting impression of a lackluster John Connolly reading from the Fifth Amendment card. (3.20.134)

    The Fifth Amendment, by the way, gives citizens the right to not incriminate themselves in court. After decades of cooking the books and bullying anybody who peeks too closely at his deal with Bulger, Connolly is finally getting his feet held to the fire. And poor wittle Connolly hates to have his toesies singed.


    [Connolly] now stood formally charged with leaking information to Bulger and Flemmi that led directly to the murders of three potential witnesses. (e.31)

    To be honest, we doubted that Connolly would ever be brought to justice for his crimes. He's great at covering his tracks, and FBI agents are rarely seen on the other side of jailhouse bars. So good on you, Lady Justice: you mind be blind as a bat, but you're a crack shot.