Study Guide

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

By Dick Lehr and Gerard O'Neill

  • Justice and Judgment

    If you hate injustice, then Black Mass might drive you clinically insane.

    Documenting perhaps the most heinous example of corruption in FBI history, the book follows Whitey Bulger, a big-time Boston gangster who's just scored a new gig—as an FBI informant.
    Instead of helping the government take down the bad guys, however, Bulger makes the government help him, using their protection to escape punishment and build up his own criminal empire. It's enough to drive you up the wall. Thankfully, Whitey's cockiness eventually catches up with him, and Lady Justice lands the final blow in the battle of the Bulger.

    Questions About Justice and Judgment

    1. In what ways does the Organized Crime Squad subvert justice? Could it be possible for them to pursue justice with Whitey as an informant?
    2. What personal characteristic of Fred Wyshak help him bring Bulger to justice? What about his personal history?
    3. Is Bulger fittingly punished for his crimes? Defend your position.
    4. Is there anyone who escapes justice by the end of Black Mass? If so, explain.

    Chew on This

    Signing an informant deal with Bulger was the beginning of the end: it was impossible for that relationship not to subvert justice.

    Using Bulger as an informant was a valid way for the FBI to bring other gangsters to justice, and it could've remained useful had it not been for John Connolly's corruption.

  • Community

    Community can be a great thing. It can make you feel safe. It can make you feel welcome. It makes you feel all sorts of good feels and then some.

    There are, of course, some downsides, and all of them are on full display in Black Mass.

    South Boston is an incredibly insular place, defined both by its Irish-American heritage and its utter hatred for outsiders. Because of this insularity, men like John Connolly and Whitey Bulger are able to dominate the hood, taking advantage of these tight social bonds to exploit the people at the bottom of the ladder. In a truly twisted move, Bulger and Connolly twist South Boston's communal values and turn them against it.

    Questions About Community

    1. What characterizes South Boston as a community? How might it be different than other communities in the surrounding area?
    2. What is your assessment of the leaders of South Boston as depicted in the book? Do they do right by their constituents?
    3. How does the community of Southie play into Connolly's relationship with Bulger?
    4. Why does Bulger come to define South Boston? What does that say about the community?

    Chew on This

    The most defining characteristic of the Southie community is its insularity: its resistance to outsiders, especially those who want to change it.

    The only reason the Bulger deal becomes so corrupt is because Connolly and Bulger have tight community ties.

  • Power

    If there's one thing that Boston could use a lot less of, based on Black Mass, it's people with power.

    You have gangsters like Whitey Bulger who use violence and intimidation to get their way. You have FBI agents like John Connolly who happily break the rules and endanger innocent lives. You even have politicians like Billy Bulger, Whitey's little bro, who put on a pretty public face but are likely getting into some serious dirt behind the scenes.

    In each of these instances, Black Mass reveals the serious consequences to such flagrant abuses of power.

    Questions About Power

    1. What are some examples of people who use their power corruptly? Who uses their power in a just manner?
    2. Does Billy Bulger exploit his power as a senator? Why or why not?
    3. How does Bulger hold power over South Boston? Is there any psychological element to his domination of the neighborhood?
    4. How do Fred Wyshak and Jeremiah O'Sullivan differ in their uses of legal power? What does this say about each respective man?

    Chew on This

    Billy Bulger exploits his power as a senator because he acts as a legal cover for many of Whitey's illicit activities.

    Fred Wyshak differs from Jeremiah O'Sullivan because he's not concerned with gaining greater power for himself within government, but rather simply with finding justice.

  • Visions of Southie

    South Boston—or Southie as it's called by those in the know—is a place unlike any other. Defined by its Irish-American population, Southie is very definition of "mean streets."

    Residents hate outsiders, love the church, and believe that there's no greater crime than ratting out your neighbors. When prominent men like Whitey Bulger enter the scene, however, there's little that residents can do to stand his way, especially when Bulger has all the neighborhood's leaders in his back pocket.

    As a result, the Southie depicted in Black Mass is one littered with contradictions, contradictions that are nowhere more evident than where Bulger is concerned.

    Questions About Visions of Southie

    1. How is Southie shaped by the neighborhood's Irish-American roots?
    2. How does Southie change over the period depicted in the book?
    3. What is the net effect of Bulger's criminal activity on Southie? How does he manage to retain control for so long?
    4. How does class play into South Boston's self-image?

    Chew on This

    Southie's Irish-American ethnic roots make it especially hostile to outsiders who share a different culture than its own.

    Although South Boston clearly suffers during Whitey' reign of power, there's hope for it to grow stronger now that he's been brought to justice.

  • Criminality

    You think Biggie Smalls was a true OG? The Notorious One doesn't have anything on Whitey Bulger.

    One of the most brutal gangsters ever seen in the Irish-American hood of South Boston, Bulger rules the city's criminal underworld for decades. Of course, he has a little help from his friends: a few corrupt FBI agents, for one.

    Aided by his G-men pals, Bulger stacks up a body count that would make Voldemort jealous, dominating everything from drugs to gambling to vending machines. He might be a criminal, but the Whitey portrayed in Black Mass sure isn't common.

    Questions About Criminality

    1. Can John Morris and John Connolly be considered criminals? Defend your position.
    2. In what ways does Whitey Bulger differ from an ordinary criminal?
    3. Can Bulger truly be considered a "chessmaster" of crime? Explain.
    4. Is Steve Flemmi an effective informant? Why or why not?

    Chew on This

    Bulger can be considered a "chessmaster" when it comes to crime: he exploits the FBI's informant deal to its maximum benefit.

    Bulger can't be considered a "chessmaster" when it comes to crime: he simply lucks into the best FBI informant deal of all time.

  • Violence

    Whitey Bulger loves portraying himself as a good-natured anti-hero, but the dude is actually a mass murderer. He doesn't just kill as a means to an end, either; he seems to get a rush from inflicting violence. Yikes. Someone needs therapy.

    To make things worse, Bulger's brutality throughout Black Mass is basically sanctioned by the FBI, who've long had Bulger on their payroll as an informant and have protected him from prosecution—even when accused of murder. As you can imagine, this one is not going to be pretty.

    Questions About Violence

    1. Is Connolly responsible for Brian Halloran's death? Explain.
    2. Does Whitey love violence? Defend your position with specific examples.
    3. How does Whitey justify his use of violence with himself?
    4. In what ways does Whitey's upbringing contribute to his use of violence?

    Chew on This

    Although Whitey claims to only use violence as a tool, his euphoria after killing Brian Halloran reveals him to be a sadist.

    Although he never pulls the trigger, John Connolly is directly responsible for numerous deaths.

  • Manipulation

    He might be morally bankrupt, but you've got to hand it to Whitey Bulger: the guy's an expert manipulator.

    Sometimes he manipulates other gangsters, buddying up only to pull the rug out and kill them dead. Sometimes he manipulates the FBI, using his informant status to get away with countless crimes, including murder. Always be manipulating: it's the Bulger way.

    And don't think that Bulger is the only shady character in Black Mass. Whether we're talking about John Connolly, John Morris, or Jeremiah O'Sullivan, a lot of shady stuff goes down where Whitey Bulger is concerned.

    Questions About Manipulation

    1. What techniques does Whitey Bulger use to manipulate John Connolly and John Morris?
    2. At what point do Morris and Connolly cross a line in their protection of Bulger?
    3. How do Flemmi and Bulger differ in their approach to the informant deal?
    4. How does the political and cultural nature of South Boston allow Bulger to manipulate the FBI so easily?

    Chew on This

    The primary way that Bulger manipulates the FBI is by portraying himself as an anti-hero: a good guy who sometimes does bad things.

    The insular nature of South Boston makes it easier for Bulger to manipulate those around him.

  • Rules and Order

    If you hate to hear about people breaking rules, then you better stay away from Black Mass.

    Whitey Bulger, a notorious Boston gangster, has a secret: he's an informant for the FBI. And not just any informant. The informant. To protect their top dog, FBI agents John Connolly and John Morris do a lot of suspicious things: forging paperwork, burying intel, and in some cases even leaking information to Bulger. That's got to be against regulation.

    Although government agencies like the FBI are supposed to be bound to the law without qualification, Black Mass shows how quickly the law can be tossed aside.

    Questions About Rules and Order

    1. What leads John Morris to so blatantly subvert FBI protocol, despite having formerly been a model agent?
    2. What sort of unspoken rules are broken by the FBI's relationship with Bulger?
    3. How does the FBI's deal with Bulger contribute to the chaotic environment of South Boston?
    4. What is the most morally egregious lawbreaking committed by the Organized Crime Squad?

    Chew on This

    While it's immoral for the Organized Crime Squad to do anything to protect Bulger, they cross a moral line when their actions lead to deaths.

    John Morris seems to be driven towards breaking FBI rules by a combination of insecurity and a good old-fashioned mid-life crisis.