Study Guide

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

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

In 1975, a low-level Boston gangster named Whitey Bulger makes the deal of a lifetime: he becomes an informant with the FBI.

(Yeah, we know. You're hooked on this story already.)

Brought on by agent John Connolly, a former childhood friend, and given protection by agent John Morris, Bulger immediately starts feeding the FBI inside intel on his foes, usually as a roundabout way to benefit himself. Clever boy.

Things get corrupt fast. It starts when Bulger is accused of shaking down a restaurant owner, with Morris and Connolly diverting attention from their favorite informant, and just continues from there. Race-fixing scandal with Bulger clearly involved? No biggie. Bulger's name being mentioned recorded on FBI wiretaps? Not the way Connolly hears it.

As the years pass, Bulger becomes the most well-known—and powerful—gangster in all of Boston. This is, of course, due to the support of the FBI, have protected Bulger from prosecution time and time again by the time the 1980s roll around. It also helps that Whitey's little bro, Billy, is a prominent politician, having served as the president of the Massachusetts state senate for years.

Meanwhile, Whitey's deal with the FBI has gotten downright dirty. Connolly gives Bulger a heads-up when a low-level G named Brian Halloran is going to rat him out, so Bulger straight up murders him. The DEA and Boston PD have also honed in on Bulger by this point, but Connolly always manages to disrupt their investigations.

This corrupt crew—Connolly, Morris, Bulger, and another informant named Steve Flemmi—start holding meetings at Morris' home, where they discuss their dirty deal and how to protect it from nosy agents. It's at one of these fateful meetings that Morris makes Flemmi and Bulger an important promise: they'll be free from prosecution as long as they don't kill anyone.

But kill they do, continuing to build up their criminal empires until one fateful day in 1995 when the FBI, led by prosecutor Fred Wyshak, finally takes its shot at Bulger and Flemmi. They're both indicted as part of an investigation into the Mafia and, though Bulger manages to skip town (thanks to a tip from Connolly), Flemmi is caught soon after and lands behind bars.

As a legal defense, the mobsters' lawyer Anthony Cardinale argues that Bulger's status as an informant—which has been rumored for years—should cause the case to be thrown out. In order to decide whether this argument is valid, the judge must make public all available information on the FBI's deal with Bulger.

This'll go swell.

So the judge orders the information released, and it's like a bombshell goes off in Boston. John Morris is given immunity in exchange for his testimony against Bulger, while Connolly refuses to do anything except plead the Fifth. When everything's said and done, however, Flemmi is sentenced to prison, presumably for the rest of his life, as is Connolly, who's officially convicted as an accessory to murder in 2008.

As for Bulger, the gangster stays on the run until 2011, when he's discovered in Santa Monica, California, living under an assumed name with his long-term girlfriend. They were discovered after a neighbor recognized them on the FBI's Most Wanted list. Although it's taken about sixteen years for the feds to catch up with Whitey, this brutal gangster is about to meet a little thing called justice.

  • Prologue

    • The year's 1948. It's a hot summer day in South Boston, and "a shy kid" named John Connolly is dropping by the corner store with his bros.
    • All the sudden, they notice a legendary neighborhood street tough: Whitey Bulger. Though still a teen, Bulger has a big reputation as a member of the hilariously named Shamrock Gang.
    • Irish much?
    • In fact, because everyone around here is Irish, Bulger buys a round of ice cream. Connolly describes this experience as being as thrilling as meeting a famous baseball player.
  • Chapter 1—Part I

    1975

    • An older John Connolly, now an FBI agent, is parking his beat-up junker in the town of Quincy, just outside of Boston.
    • He's meeting up with a "contact" (which we presume to mean "informant") who also grew up in South Boston, called "Southie" by those in the know (1.1.1).
    • Connolly has been a part of the FBI for a bit, but he was just transferred to his hometown a year ago, which was a welcome development for him.
    • As it happens, the FBI is in the midst of an internal crisis. The bureau has received a ton of bad press in recent years for secretly monitoring politicians and public figures.
    • Hmm, we wonder why.
    • To cover up this PR snafu (the understatement of the year), the FBI has set its sights on dismantling the Mafia, the Italian-American criminal organization that's dominating the underworld.
    • Finally, we learn the identity of Connolly's contact...it's none other than Whitey Bulger, the street tough from the prologue.
    • Another agent, Dennis Condon, had tried to turn Bulger into an informant a few years back in 1971, but failed harder than a basketball player working against the Based God's curse.
    • Now, however, it's 1975, and Connolly is confident that his neighborhood ties with Bulger will help seal the deal.
    • He begins his pitch in a rather unusual manner: by telling Bulger that he should make use of his "friends in law enforcement" (1.1.11).
    • Shady.
    • Turns out that Bulger could use a friend right now. Boston is experiencing some serious changes, not the least of which being a federally led effort to integrate its school system.
    • Many residents of Boston are in an uproar over this, and leading the charge is a certain local political leader named Billy Bulger—Whitey's little brother.
    • The criminal world is changing too. Whitey has sparked a relationship with the Winter Hill gang, particularly bonding with a ridiculously named mobster named Stevie "The Rifleman" Flemmi.
    • The Winter Hill gang, like the FBI, is currently beefing with Boston's resident Mafia, led by "the powerful underboss Gennaro J. Angiulo and his four brothers" (1.1.20).
    • So, basically, Connolly wants Bulger to rat out on the Mafia—which is a huge no-no in the criminal world.
    • After the meeting, Connolly asks Flemmi for advice, which is hilarious because Flemmi has been an informant since the '60s. He was recruited by Agent H. Paul Rico, former partner of Condon.
    • Although not officially in the Mafia, Flemmi has friends on the inside, like childhood buddy "Cadillac Frank" Salemme, and has been trading information for protection from the FBI.
    • In the late '60s, Flemmi had been wanted for several murders, but Rico would tell him when the feds were coming for him, helping him to stay on the lam for four years until the charges were dropped.
    • So, uh, this is just straight-up corruption, huh?
    • Flemmi isn't sure if Bulger knows this, but he heartily recommends that Bulger take up Connolly on his offer. Can't pass up a deal like that.
    • Two weeks later, Bulger agrees to the deal. This is a huge win for Connolly, as Bulger is a prominent gangster in the region.
    • And, absurdly, five weeks after that fateful handshake, Bulger commits his murder while on the FBI payroll—but far from his last.
  • Chapter 2

    South Boston

    • When he got back to Boston in 1974, Connolly learned that Bulger "was the preeminent Irish gangster" in Southie, which sounds like a great blurb for a LinkedIn profile (1.2.4).
    • Connolly and Bulger had grown up in the same housing project in Southie—the first in Boston.
    • South Boston has a unique culture defined by its Irish-American population. The Catholic Church is the center of social life, outsiders are heaped with scorn, and internal traditions are revered. People tend to stick around, too.
    • Though Boston has been around for two hundred years, it doesn't become an Irish-American stronghold until after the Civil War, when they move into the city to find work, developing an often-contentious relationship with Boston's Italian-American population.
    • Although the community starts off strong, developing a strong base of Church-centric social institutions, Southie is slammed by the Great Depression, as is the rest of Boston.
    • In 1938, the Bulger family moves into Southie, which is still reeling from the aforementioned economic apocalypse. Whitey is eleven.
    • James Bulger, Whitey's dad, had "lost much of his arm when it was caught between two railroad cars" (1.2.16). He was a quiet guy who kept to himself for the most part. Billy takes after him.
    • Billy first runs for political office in 1960. He quickly rises the ranks in the state senate and "went on to be president of the chamber longer than any man in Massachusetts history" (1.2.19).
    • Billy is a Southie guy, through and through. He fiercely fights to "protect" his community from outsiders, as with his opposition to the forced integration efforts led by the feds.
    • When he was a kid, Connolly was tighter with Billy than Whitey, who Connolly only knew as a notorious neighborhood troublemaker.
    • When Connolly is born, Whitey is thirteen, and he's already taking stuff from trucks to sell on the streets.
    • Dang. We were mostly concerned about Pokémon at that age.
    • Whitey has a long stint in federal prison when he's twenty-seven, and even ends up in Alcatraz, one of the most notorious prisons in American history.
    • He's released after nine years, and immediately moves back in with his mother in her Southie apartment. Shaken by prison, Whitey promises himself that he'll never go back.
    • After his release, Whitey works for Donald Killeen, a bigwig bookmaker. Bookmakers run illegal betting markets, by the way.
    • Being a shady guy, Whitey betrays Killeen to earn cred with the Winter Hill gang, Killeen's chief rivals. And by "betray" we mean "assassinate."
    • Yup. Whitey is one nasty character.
    • Although Whitey has made a bunch of money and killed a lot of people, he lives a frugal, spartan lifestyle that set him apart from most of Boston's gangsters.
    • That doesn't mean he's a nice guy. Bulger is feared across the streets of Southie, and Ellen Brogna, wife of Howie Winter, says that Whitey "chilled her" like no other mobsters (1.2.45).
    • So, given their mutual Southie roots, it's perfect that Connolly and Bulger have ended up together. They're like two corrupt peas in a rotten pod.
    • In fact, Bulger quickly breaks his own promise and starts informing on not just the Mafia, but also his fellow Irish mobsters. That's a huge no-no in the hood.
    • Overjoyed, Connolly spreads Bulger's reports around the FBI to critical acclaim, not just earning cred for himself, but also the brutal Whitey Bulger.
  • Chapter 3

    Hard Ball

    • Local District Attorney William Delahunt is going to a dinner meeting with a few other government prosecutors. He's heading over to the restaurant now.
    • Unbeknownst to him, the restaurant is also being visited right now by Whitey Bulger and two other gangsters who are trying to shake down its owner for $175,000 dollars.
    • In fact, Delahunt knows one of these gangsters—Johnny Martorano—from childhood. The two "former school chums" immediately notice each other and start chatting (1.3.3).
    • Their repartee quickly becomes an argument, and the two men separate—but not before Delahunt recognizes one of Martorano's bros as Stevie Flemmi.
    • Although Delahunt doesn't know it at the time, the gangsters, led by Bulger, later assault restaurant owner Francis Green to force him to pay back the debt he owes them.
    • Green had seen Martorano mingling with Delahunt that night, so he's freaked out. In a panic, he contacts Richard Harrington, "the former chief prosecutor at the federal Organized Crime Strike Force for New England" (1.3.12).
    • When asked about the meeting with Martorano, Delahunt assures Harrington that it was nothing but a chance encounter, but is eager at the inadvertent opportunity to take down Bulger.
    • They decide to pass off the case to the FBI, as bureau will have more resources to take down the gangsters. This turns out to be a major mistake.
    • The report lands on the desk of Connolly, who does some perfunctory investigation before claiming that "Green was reluctant to testify" against Whitey, which isn't true at all (1.3.21).
    • This is the first but far from the last time that Connolly will sweep one of Bulger's crimes under the rug.
    • Delahunt can't understand why the FBI doesn't want to pursue this slam dunk case, but gets a hint five years later after he cuts a deal with an informant named Myles Connor, who works with Bulger.
    • Connor is a fascinating guy: he's a rock musician, certified genius, art thief, and murderer. (We were writing up wedding proposals up until the last one.)
    • Delahunt knows that his deal with Connor is controversial, but he's shocked by just how hard Connolly works to keep Connor's story under wraps. Not to mention suspicious.
    • The story is eventually leaked to the media, and Connolly proves himself to be as adept at working reporters as he is with covering up crimes.
  • Chapter 4

    Bob 'n' Weave

    • Paul Rico, Dennis Condon, and John Connolly all believe that Bulger and Flemmi are vital to the FBI's efforts to take down the Mafia, and will do whatever it takes to protect them.
    • During the reign of FBI director J. Edgar Hoover, the agency had notoriously ignored the Mafia in favor of political witch-hunts, and it's not until the '60s that things slowly begin to change.
    • In fact, Dennis Condon and Paul Rico are some of the first employees at Boston's "first-ever Organized Crime Squad," which TBH sounds like a supervillain dream-team (1.4.5).
    • The Squad sets their sights on Gennaro J. Angiulo, who runs the Mafia in New England.
    • Over the course of the '60s, Congress passes a series of bills meant to layeth the smackdown on the Mafia.
    • These laws allow the feds to more easily monitor Mafiosos through electronic means and charge them with federal crimes.
    • The big one is the Racketeering Influenced and Corrupt Organizations Act, better known as RICO. This law allows federal agents to send gangsters behind bars for decades if they can prove that they're involved in shady business dealings across multiple states.
    • Despite these fancy new legal tools, the most powerful weapons in the FBI's arsenal are informants. This is well attested to in the FBI's training material, and is highly encouraged by its internal culture.
    • The FBI uses a lot of electronic surveillance during this period, often in legally suspect ways. Because these illegally-acquired recordings often could not be used in court, the onus is still on informants to take down the mob.
    • Of course, there are tons of regulations meant to keep agents from getting too tight with informants, but there's enough wiggle room for guys like Connolly to weasel their way through.
    • Rico lets Flemmi get away with a bunch of crimes, for instance, many of them violent in nature.
    • Now it's Connolly's turn.
    • He's faced with another investigation into Flemmi and Bulger: a vending machine company called National Melotone is making complaints to the FBI that the two gangsters are intimidating local shop owners into using their vending machines, rather than the company's.
    • And of course Connolly is charged with investigating the claim against Bulger.
    • He intimidates the company's executives into dropping the matter and goes on his merry way.
    • Around this time Connolly starts acting weird—more like a "salesman" than an FBI agent (1.4.46).
    • He divorces his wife and move across the street from Bulger's girlfriend, Catherine Greig. Because that's not weird.
    • Some FBI bigwigs notice this behavior and assign Connolly a new supervisor, John Morris, who is seen as a potentially cooling force on the volatile Connolly.
    • Spoiler: it doesn't work.
  • Chapter 5

    Win, Place, and Show

    • The White Hill boys—including Howie Winter, Flemmi, and Bulger—are eagerly awaiting the results from the Suffolk Downs Racetrack, where they've rigged a race with "Fat Tony" Ciulla.
    • Unfortunately for them, the paid-off jockey decides to win instead of losing, effectively tossing the gang's money down the drain.
    • They beat the living tar out of him and called it a day.
    • Here's how the scheme is supposed to work: Ciulla uses "bribes and intimidation" to force jockeys into specific outcomes, while the Winter Hill gangsters place big bets with a wide group of bookies (1.5.11).
    • And bam—you now have a bunch of cash.
    • Things go bad when Ciulla is busted by the FBI.
    • In 1976, he decides to inform on the gang and go into the witness protection program.
    • Because Bulger and Flemmi are now subject to a criminal investigation, they can no longer be active FBI informants.
    • Uh-oh for Connolly's pet project.
    • Connolly and Morris do all the paperwork to take Bulger and Flemmi off the books as informants, but never actually stop meeting them.
    • They never even mention it to the gangsters.
    • This is the first sign of corruption from the previously disciplined Morris.
    • To be fair, he has bigger things on his mind: a probe into the "widespread hijacking of trucks in New England" called "Operation Lobster" (1.5.26).
    • Sounds tasty.
    • In the probe, an FBI agent named Nick Gianturco is posing as a purchaser of stolen merchandise. So far he's recovered around $2.6 million worth.
    • One night, Flemmi mentions Gianturco to Connolly, not realizing that he's an undercover agent, and claims that some gangsters are considering taking him out.
    • Connolly interprets this vague warning to an immediate threat and calls Gianturco in a panic, telling him not to go to an upcoming meeting.
    • So he doesn't.
    • Naturally, Connolly builds up the story bigger and bigger until Bulger and Flemmi seem like gosh-darned heroes.
    • They saved an agent's life. Much wow.
    • By 1978, however, the race-fixing case is gaining steam.
    • Howie Winter is already in jail for unrelated charges, but Flemmi and Bulger are totally exposed.
    • So, in January 1979, Connolly and Morris visit Bulger at his apartment, where Bulger falsely claims that he has nothing to do with the fixed races.
    • And they believe him without question, because that is totally the right thing to do when investigating a criminal.
    • The two agents visit Jeremiah T. O'Sullivan, the chief prosecutor in the case, and reveal that Bulger and Flemmi are informants.
    • They also back Bulger's claim that he didn't fix any races.
    • O'Sullivan takes some time to think about it, but ultimately decides to side with the agents and neglect to prosecute Flemmi and Bulger.
    • Fat Tony is incredulous: he gave them everything they needed to prosecute the gangsters on a silver platter, and nothing?
    • This is a joke.
    • The investigation concludes in February and includes pretty much everyone in Winter Hill not named Bulger or Flemmi, though the pair does warn a few pals to skip town before the hammer comes down.
    • That summer, John Morris decides "to host a party at his home" to celebrate Bulger and Flemmi being officially reinstated as FBI informants (1.5.74).
    • As you can guess, his wife is ticked off.
    • It's at this clandestine meet-up that Bulger and Flemmi get the impression that the FBI has given them a license to commit crime.
    • After all, they're now unaffiliated after the fall of Winter Hill.
    • So they decide to fill up this power vacuum themselves, "making the rounds to independent bookies" and forcing them to pay protection money (1.5.87).
    • One such bookie is Burton K. "Chico" Krantz, one of the most legendary in the region.
    • Connolly and Morris don't do jack to stop their informants from rising to the top of Boston's criminal underworld, however.
    • Far from it—they act like friends.
  • Chapter 6—Part II

    Gang of Two?

    • It's 1980 and Bulger and Flemmi are at their new haunt: Lancaster Foreign Car Service, run by fellow gangster George Kaufman.
    • Nick Femia, an "enforcer with a reputation as a killer" is also there, being his usual sunny self (2.6.2).
    • Bulger has been tearing his way through the Boston underworld.
    • The only dark spot is the death of his mother on New Year's Day.
    • To comfort himself, he spends his days either with his long-term lady friend Teresa Stanley or his backup lady friend Catherine Greig.
    • Guy's got options.
    • At the same time, Billy Bulger is becoming quite powerful himself, having become senate president in 1978.
    • Those Bulger boys are off the charts.
    • Unbeknownst to Bulger and crew, however, they're being watched by the Massachusetts State Police.
    • The police have been monitoring the garage for months since stumbling upon it in April.
    • It's hard work, but they get some amazing insight into the tight relationship between Bulger and the mob.
    • Led by Sergeant Bob Long, the police bring their intel to Jeremiah T. O'Sullivan (remember him?) to get federal funding in to wiretap the garage.
    • Wiretapping is pretty hard as it turns out.
    • The troopers first try to sneak in microphones inside a car, but that plan crashes and burns.
    • They nail it on their second try, however, using trucks to block the garage from sight and breaking in under the cover of night.
    • As soon as the mics are up and running, however, Bulger and Flemmi suddenly stop talking.
    • In fact, they avoid going into the office altogether.
    • Suspicious, right? Even more suspicious is that John Morris sidles up to a Boston police officer at a party on night and implies that he knows about their bugging operation.
    • This causes a big snafu between the Boston Police and the FBI, and the two agencies hold a big conference to make peace.
    • The meeting only stokes the fires further, with the FBI claiming that they have evidence that the State Police is responsible for the bug being leaked.
    • And who's making this "new juicy intelligence claim" (2.6.65)? Mr. John Connolly.
    • The troopers try again, tailing Bulger and Flemmi as they drive between pay phones and installing bugs at their favorite stops. Once again the gangsters change their habits as soon as the bugs are planted.
    • They launch their boldest plan yet in 1981: install a bug in Bulger's famous "black Chevy" (2.6.77).
    • Flemmi is driving the Chevy alone one day, so they pull him over and claim that the car is stolen. They'll then tow the car away, plant the bug, and give it back. Easy-peasy, right?
    • As soon as they pull over the Chevy, however, Flemmi calls out several troopers by name and loudly announces that he knows about the bug.
    • These suckers are crafty.
  • Chapter 7

    Betrayal

    • By now, the police strongly suspect that Connolly tipped Bulger off.
    • But it wasn't just Connolly—he had only learned about the bug because Morris told him.
    • It gets even juicier—Morris supposedly received the intel from O'Sullivan, though most of the participants continue to dispute this.
    • There's one man who's skeptical of Bulger, however: Lawrence Sarhatt, "the new FBI boss in town" (2.7.5).
    • Buoyed by the police's complaints about Morris, Sarhatt launches an investigation into whether Bulger is even worth the trouble for the FBI.
    • Connolly is furious at Morris for being so loose-lipped with the police.
    • As for Morris, his life—and not coincidentally, his marriage—is falling apart.
    • But Connolly has a plan.
    • He's going to get Bulger and Flemmi credit for "the biggest case ever in the history of the Boston FBI office—the bugging of the Angiulo headquarters" (2.7.10).
    • To plant the bug, the FBI needs to win permission in court, and to do that, they need to collect evidence.
    • A lot of it.
    • They have more than enough intel to win the case already, but Connolly slips in a rather irrelevant tip from Flemmi and Bulger to get them credit.
    • And it works like a charm.
    • Of course, the bugging efforts will surely reveal evidence of Flemmi and Bulger's crimes, but the agents promise them that they won't be prosecuted.
    • In a crazy move, Connolly writes an internal memo which claims that the campaign against Bulger is based on political opposition to his brother Billy.
    • It's conspiracy theory stuff.
    • Not a good look, Connolly. Sarhatt certainly feels that way, at least, and the memo only makes him more skeptical of Bulger.
    • At the end of the day, however, Sarhatt signs off on Bulger's contributions to the Angiulo bugging, and the corrupt informant continues kicking butt with the FBI's okay.
    • The police, clear losers in this inter-agency battle, are forced to lick their wounds and prepare to fight another day.
  • Chapter 8

    Prince Street Hitman

    • FBI agents are in the midst of their clandestine operation to bug Angiulo HQ.
    • They make it inside Jerry Angiulo's office, install the bug, and skedaddle.
    • The agents hang on every word that comes through the bugs. Angiulo thinks that he has the upper hand, while at the same time basically confessing to his crimes on tape. Smart guy.
    • Angiulo often complains that he hasn't seen Bulger and Flemmi in a while, but assumes that it's because they owe him money.
    • We can think of a different reason.
    • No matter what's said about Bulger and Flemmi, however, Connolly and Morris manipulate their reports on the bug to make the two brutal gangsters seems as cuddly as Teletubbies.
    • They also conveniently forget to mention that the debt Angiulo keeps complaining about stems from their mutual "loan sharking" business (2.8.45).
    • Whoops.
    • The investigation—known as Operation Bostar—ultimately eviscerates the Angiulo crime family.
    • But Morris is in a tailspin.
    • He gets so drunk with Connolly, Flemmi, and Bulger at a hotel that he leaves behind a "top-secret government tape recording" from the case, which is only recovered by Flemmi–a criminal, mind you (2.8.55).
    • How's that for an anti-drinking PSA?
  • Chapter 9

    Fine Food, Fine Wine, Dirty Money

    • At this point, "the boundary lines between the good and bad guy" has been thoroughly blurred (2.9.1).
    • While Connolly embraces his new edge with aplomb, Morris still can't get over his sense of guilt.
    • In '81, word spreads that Bulger is dipping his toes in the cocaine business. This contradicts Connolly's claims about Bulger, as well Bulger's own stated anti-drug stance.
    • In particular, these claims revolve around two men: Nick Femia, who we met back in the Lancaster Garage, and a local hitman named Brian Halloran.
    • Naturally, Morris removes all of Bulger's identifying details from any internal reports on his drug ties.
    • At the same time, Connolly spruces up every single one of Bulger's small claims to make it seem like the evidence of the century. They're a well-oiled machine.
    • Connolly likes to claim, for example, that Bulger saved Gianturco from certain death, which is quite the exaggeration.
    • Ever since their first dinner party in 1979, the crew has continued to meet each other off the clock, often at Morris' house. Morris' wife is about ready to throw her hubbie out the window.
    • The gangsters also start exchanging gifts with the agents, which is so corrupt it hurts.
    • It's usually something small: a case of wine here, a fancy new belt buckle there.
    • But then, one day, while on a business trip in Georgia, Morris asks Bulger to buy plane tickets for Debbie Noseworthy, his secret girlfriend, so she can visit him.
    • And, with that, John Morris' trip to the dark side is complete.
  • Chapter 10

    Murder, Inc.

    • Brian Halloran is meeting with John Callahan, an accountant for "a company called World Jai Alai that was a gambling cash cow" (2.10.3).
    • They're on their way to see Bulger and Flemmi to discuss the assassination of Roger Wheeler, the new CEO of the World Jai Alai Company.
    • Wheeler is digging a little too deep into Callahan's shady dealings with Bulger for Bulger's liking, so what's a violent gangster supposed to do?
    • Halloran has killed people for Bulger before, but this is different. Wheeler's not some schmohawk from the streets: he's "a multimillionaire from Tulsa with seven corporations" to his name (2.10.11).
    • Bulger ultimately chooses a different assassin—Johnny Martorano—to kill Wheeler. Martorano shoots the businessman in broad daylight as he exits his Tulsa country club.
    • Although Halloran is relieved he wasn't chosen for the job, he knows that this puts him squarely on Bulger's bad side, which is not where you want to be.
    • That, along with Halloran's increasing drug addiction, means that things aren't looking so good for him right now.
    • He hits rock bottom in late 1981 when he brutally murders a drug dealer named George Pappas. After hiding out for a few weeks, he turns himself in and is released on bail.
    • Of course, this only puts him even further on Bulger's bad side. Tough spot.
    • Flemmi tells Connolly that the Mafia is thinking about killing Halloran, which really means that he and Bulger are planning on it. Because of course they are you dummies.
    • Faced with serious jail time, Halloran decides to become an informant.
    • This sparks an internal war within the FBI: some want to offer Halloran greater protection, while others, led by Connolly, see him as untrustworthy and unreliable.
    • O'Sullivan is one of the key figures pushing back against efforts "to get the Winter Hill snitch safely off the streets" and into witness protection (2.10.35).
    • While this is happening, Connolly gives Bulger frequent updates on the comings and goings of the investigation.
    • What a good FBI agent he is.
    • Robert Fitzpatrick, one of Halloran's chief defenders, even accuses Connolly of snooping through his files on Halloran to dig up dirt. Connolly just keeps getting shadier.
    • In 1982, Halloran—who's been staying out of Southie to stay alive—returns home to meet his sister at a bar. Bulger finds out and immediately heads over with Patrick Nee and Kevin Weeks.
    • The trio brutally murders Halloran in the middle of the street.
    • Bulger is so thrilled by the experience that he's "unable to talk about anything else for days" (2.10.51).
    • Although some suspicion is thrown Bulger's way after the killing, Connolly is able to deflect it like a pro. He deflects blame as well as Serena Williams plays tennis.
    • Morris, on the other hand, is ashamed for his part in Halloran's grisly death.
    • Meanwhile, the Tulsa police are investigating Roger Wheeler's death, and have figured out that John Callahan is involved. They order him to appear before a federal grand jury.
    • Connolly informs Bulger of this, and Bulger has Callahan killed. They're not even subtle about it at this point, huh?
  • Chapter 11

    Bulgertown, USA

    • Julie and Stephen Rakes are lifelong residents of Southie. After holding joint ownership over several small businesses, they decide to open their own liquor store in 1982.
    • But Stephen is "worried he'd gotten in over his head" (2.11.7).
    • Without telling Julie, he discusses handing the store over to a certain local gangster named Whitey Bulger.
    • Unbeknownst to her, Bulger and Flemmi frequently visit the construction site with Kevin Weeks, Bulger's most devoted protégé.
    • Stippo's Liquor Mart, as it's known, opens in 1984 and does shockingly good business. It helps that the store is holding a raffle for a free Hawaii vacation. We'll take two tickets please.
    • Sadly, the raffle never gets held. We want a refund.
    • One night, Bulger and Weeks show up at Stephen's home while Julie is at the store, threatening him with a gun in front of his kid when he says that he has second thoughts about their deal.
    • And with that, Bulger is the new owner of Stippo's Liquor Mart. Good timing, too: he's been looking for a new HQ ever since the Lancaster garage was busted wide open.
    • A few days later, Julie and Stephen meet with Julie's uncle, Joseph Lundbohm, who's a detective with the Boston PD.
    • Lundbohm thinks that the case is a slam dunk, but needs some federal backing, so he turns to...the FBI.
    • Bad move, Joey.
    • And of course he meets with Connolly.
    • Connolly implies that Stephen and Julie will have to wear a wire and meet with Bulger, which is a classic intimidation tactic. Even the toughest gangster wouldn't do that.
    • And then, a few days later, Stephen tells Lundbohm to drop the investigation. Bulger threatened Lundbohm by name.
    • Bulger doesn't have any more problems with Lundbohm after that. He even intimidates Rakes into falsely testifying in court in Bulger's defense, which ultimately gets Rakes charged with perjury.
    • Ouch. Talk about rubbing salt in the wound.
  • Chapter 12

    The Bulger Myth

    • "Detective Dick Bergeron of the Quincy Police Department" is writing out a proposal to electronically surveil Bulger and Flemmi (2.12.6).
    • He's been monitoring Bulger for months, ever since discovering that the gangster had moved to Quincy.
    • Bergeron's proposal makes its way to the Drug Enforcement Agency (DEA), who have also been investigating Bulger's drug activity.
    • The DEA and Quincy PD start a joint investigation, which they dub Operation Beans.
    • Okay, how are we not supposed to laugh at that?
    • By the mid-'80s, Southie has been decimated by drug addiction, which is spurned largely by the nominally anti-drug Bulger. He's basically destroyed his community.
    • Bulger justifies this through a loophole: he merely forces drug dealers to pay "rent" for selling their wares in Southie, but doesn't actually handle the drugs
    • Oh okay. Because that makes it totally all right.
    • The FBI learns about Operation Beans in 1984. John Morris no longer works for the Organized Crime Squad, so the matter is dealt with by Connolly and his new supervisor, Jim Ring.
    • Of course, the FBI has already heard from plenty of "informants [...] about Bulger and drugs" (2.12.42).
    • Connolly blasts these reports away like they were baddies in Call of Duty.
    • Bergeron particularly hates Bulger because he blames him for the death of one of his informants, John McIntyre.
    • McIntyre had busted open a gun-smuggling operation between Bulger and the IRA, a militant Irish revolutionary organization. Serious stuff.
    • Overjoyed with this inside info, Bergeron spread the news across federal agencies. Including the FBI. Uh oh.
    • A few days later, McIntyre is dead.
    • Bergeron is sure that Bulger is behind the murder, and suspects that the FBI had a hand in it too.
    • As a result, they share as little information about Operation Beans with the FBI as possible.
    • Still, Bulger and Flemmi remain one step ahead of the fuzz. They become increasingly insular and rarely do business face-to-face with subordinates.
    • The investigators make several efforts the bug Bulger and Flemmi, but each fails.
    • Somehow, however, they manage to plant a bug in Bulger's car while he's sleeping, which is, like, Jedi-level.
    • The only problem is that it's so noisy inside the car that's it's practically impossible to hear what's being said. Well, that defeats the purpose.
    • One night, they try to sneak into the car to fix the microphone, but Bulger sees them and runs out to chase them off.
    • He doesn't catch them, but a few days later they hear him saying the worst thing they could hear: "'He's right—they did put a bug in the car" (2.12.81).
    • He knows about the bug.
    • Hearing this, the agents rush over to retrieve the bug. Bulger laughs at them and claims that, while the cops are the "'good good guys,'" he and Flemmi are the "'bad good guys'" (2.12.90).
    • This dude is delusional.
    • For the DEA and Boston PD, Bulger's knowledge of the bug confirms their suspicions that he's being aided by the FBI.
    • And that's scary.
    • Bulger and Flemmi, on the other hand, are freaked out.
    • They decide to have a meeting with John Morris.
  • Chapter 13

    Black Mass

    • By 1985, Morris is firmly in Bulger's back pocket, having accepted money to buy his girlfriend a plane ticket, along with several other pricey gifts in the months that followed.
    • Despite this, Morris has never been more successful professionally.
    • The Angiulo racketeering trial should be starting in a few weeks, and that'll be his crown jewel.
    • Bulger and Flemmi are nervous because they're talked about all over the tapes. They want reassurance that they won't be prosecuted.
    • Plus, they're happy to see Morris again, as Connolly's new boss Jim Ring had proven to be a "tough mark" (2.13.17).
    • Connolly brings along Dennis Condon, without telling him that Bulger and Flemmi are going to be there.
    • Condon is turned off by Connolly's shadiness and leaves early in the evening.
    • It's at this dinner, on the "tenth anniversary of their secret deal," that Morris promises that the FBI won't prosecute the pair unless they're involved in a murder (2.13.51).
    • And with that, their unspoken agreement has become spoken.
  • Chapter 14, Part II

    Shades of Whitey

    • Although Billy Bulger is by now "securely on top of the State Senate," he's going through a bit of a money shortage (2.14.1).
    • So he takes out a $240,000 loan from his friend Thomas Finnerty to make up the difference until some long-awaited money comes in.
    • But then Billy learns that Finnerty has been dealing with Harold Brown, a criminally-associated Boston developer.
    • Furious at this deception, Billy immediately pays back the loan, plus interest.
    • Or at least that's how Billy tells it. Harold Brown has a totally different story.
    • The feds catch Brown in 1985 after recording him making a deal with a "corrupt city inspector" to undervalue the price of a new development to save cash on fees (2.14.8).
    • Threatened with jail time, Brown reveals that Billy Bulger and Finnerty had helped him get permission to build a skyscraper in return for a bit of back-patting, if you catch our drift.
    • Roughly $1,800,000 worth of back-pats, to be specific. Finnerty and Bulger immediately split the first payment of $500,000 between themselves: hence the $240,000.
    • There's a huge "public clamor" when this deal is made known (2.14.18).
    • Billy stands by the story we started off this chapter with, and somehow manages to whether the PR storm.
    • Of course, he has some help from the FBI. Connolly is super-happy to help Billy out, as Billy's just about the only person he admires more than Whitey.
    • After a softball interview with the FBI and a prompt dismissal by new US attorney Jeremiah O'Sullivan, Billy Bulger is officially let off the hook.
    • Coincidentally, Whitey is in the midst of a shakedown of his own, having just assaulted a man named Raymond Slinger for an unpaid $50,000 debt.
    • So the FBI investigates. That is, until Connolly appears, muddying the waters and telling Whitey to chill until things blow over.
  • Chapter 15

    Connolly Talk

    • On February 8, 1988, Connolly runs into a reporter from the Boston Globe named Dick Lehr—who, if you've forgotten, is one of the authors of this book.
    • Connolly already knows Lehr because the reporter had written a story about the Organized Crime Squad last year, though it's not like they're best bros or anything.
    • Hence why it's so weird when Connolly decides to loudly announce that the FBI is bugging the Mafia again, this time in their new secret HQ at "Vanessa's Italian Food Shop" (2.15.6).
    • Lehr is shocked, not just about the bugging operation, but that Connolly is being so open about it with a reporter.
    • So Lehr does what any reporter should: he writes a story about it, though he doesn't explicitly name-check Connolly. The FBI is ticked off.
    • As it turns out, Connolly is playing a big role in the bugging of Vanessa's, but that's mostly due to the efforts of Flemmi, not Bulger.
    • But you can bet that Bulger gets the credit.
    • Flemmi also plays a big part in the first ever secret recording of "a Mafia induction ceremony" (2.15.31).
    • Again, however, all glory goes to Bulger.
    • Connolly would sometimes even protect associates of Bulger, like when he intimidates the police into dropping a murder investigation against a thug named Mark Estes.
  • Chapter 16

    Secrets Exposed

    • With his marriage in shambles, Morris is now in a full-blown moral crisis.
    • He abruptly opposes "Connolly's bid from promotion to supervisor" despite having previously promised his support (2.16.1).
    • Instead, Jim Ahearn becomes the new supervisor of the Organized Crime Squad, which works out great for Connolly—Ahearn is a devoted buddy.
    • This is 1988, by the way, and reporters from the Boston Globe—including authors Dick Lehr and Gerard O'Neill—are working on a series on the Bulger brothers.
    • Some of them even wonder if Bulger might be an FBI informant...
    • Nah. Too unrealistic.
    • Still, they ask around just to check. Jeremiah T. O'Sullivan lies through his teeth and says no.
    • A few agents hint that they're on the right path, even name-checking Connolly in some cases.
    • In May, Morris agrees to meet O'Neill for lunch, though he stridently denies that Bulger is an FBI informant.
    • That is, until they sit down to eat.
    • As soon as they do, Morris spills the beans to O'Neill, who's in shock that he cracked the case before the appetizers even arrived.
    • The reporting staff of the Globe is "dumbstruck" (2.16.19). Before they can run the story, however, they need to vet it through other sources.
    • Two months later, after running the story by several agents, the Globe publishes its expose on the Bulger boys.
    • Notably, one installment investigates the close relationship between Whitey and the FBI, though it doesn't accuse him of being an informant.
    • The FBI is ticked, to say the least. One agent, Tom Daly, even threatens the reporters by implying that Bulger is looking to take them out.
    • In the end, however, the story blows over—as they always do.
    • Despite another victory, Connolly can't rest up yet.
    • He's also dealing with an internal probe from Bill Weld in the Justice Department, who for months has been receiving shockingly accurate calls from a woman who claims to have knowledge of Bulger's relationship with the FBI.
    • Weld resigns later that year, but his staff pick up where he leaves off, and soon enough the report lands smack dab on Connolly's desk. Another dead end.
    • Bulger is way cocky by now. One day, he tries to walk through an airport with over $10,000 in cash, getting into a fight with a police officer who tries to stop him.
    • Flemmi seems to be getting along great, on the other hand. He's taken up skydiving and travels the world. What a nice retirement for a gangster.
    • Connolly continues to meet with Flemmi and Bulger for dinner, despite being told not to, like, a thousand times. Morris is "now persona non-grata" in their little squad (2.16.67).
    • Still, there's trouble on the horizon. Despite the FBI's protestations, the DEA is pushing forward with a drug investigation into Bulger that began back in 1987.
  • Chapter 17—Part III

    Fred Wyshak

    • The Mafia, now led by "Raymond Patriarca of Rhode Island," is in rough shape, and Bulger is once again ready to pounce (3.17.1).
    • Patriarca and co. will soon go to prison after the secretly recorded initiation ceremony mentioned last chapter is played in court.
    • Bulger will fill the void, as will Cadillac Frank Salemme, Flemmi's childhood friend.
    • Connolly leaves the FBI in 1990, taking a lucrative salary as "head of corporate security at Boston Edison," a major power company (3.17.4).
    • Where's karma when you need it?
    • Bulger and Flemmi decide to chill out for a bit, investing their illegally-earned money into actual business ventures.
    • Enter Fred Wyshak, a native Bostonian who's finally returned to his hometown after cutting his teeth as a US attorney in New York City.
    • Wyshak can immediately tell that Bulger is the big fish around these parts, becoming immediately suspicious when everyone tells him to focus instead on the Mafia, which is clearly not a threat to anything but the city's spaghetti supplies.
    • Wyshak pokes around for a while to little avail, until hooking up with Brian Kelly, another federal prosecutor. The pair becomes a dream team of sweet, sweet justice.
    • Things aren't easy though. In 1989, Wyshak tries to wiretap Howie Winter, who's been released from prison, and use him to get to Bulger.
    • Winter seems one step ahead of him, however.
    • Hmm...wonder why that is.
    • Wyshak tries again in 1992, and this time he leaves the FBI out of the equation entirely.
    • The operation goes off like a dream and Winter is convicted the following year.
    • This is a similar tact to that taken by state policeman Charles Henderson "back in the early '80s," in a failed attempt to take down Bulger (3.17.34).
    • By now, however, Henderson is the head of the state police, and he's ready to finish the job.
    • By focusing on nabbing bookies, then making their way up the chain of command, both groups are able to get closer and closer to Bulger himself.
    • Despite making progress, however, Connolly continues to inform Flemmi and Bulger whenever there's an investigation aimed in their direction, giving the crooks time to get away.
  • Chapter 18

    Heller's Cafe

    • Detective Joe Saccardo of the Massachusetts state police is monitoring Heller's Cafe, which he suspects to be a front for illegal gambling.
    • And he's right: bookie Michael London is inside right now, counting checks.
    • London work with Bulger (duh), but he has a particularly close relationship with Vincent Ferrara of the Mafia.
    • This is happening during the '80s, which means that the FBI is bogging down the investigation as much as possible.
    • Anything to protect Bulger, right?
    • Still, through hard work, and the help of a prosecutor named Michael Kendall, Saccardo manages to take London down—though everyone directly connected with Bulger is still safe.
    • Saccardo wants to do another round of investigations, this time focused on a bookie named Chico Krantz.
    • To do so, he enlists the help of a certain Fred Wyshak.
    • Chico would be the perfect informant because "he had been paying tribute to the insular Bulger for nearly twenty years" (3.18.15).
    • They manage to arrest Chico in 1991. After pressuring him with legal threats, they get him in the witness protection program the following year.
    • A similar thing occurs with Jimmy Katz and Joe Yerardi, both gangsters with ties to Michael London.
    • Another arrest, another flip, and another informant in the bank against Bulger.
    • By 1994, the investigation is progressing nicely, and the feds are gathering evidence from all the way back in the '80s.
    • In the middle of the year, the feds are finally ready to make their move and arrest Bulger, Flemmi, and Cadillac Frank.
    • They want to do it fast so they don't have time to run.
    • Well, Cadillac Frank stays in town, but Bulger and Flemmi are suspiciously missing. How could that possibly be?
    • Cadillac Frank manages to escape the police to Florida, but is caught eight months later.
    • Pretty good run.
    • In 1995, Flemmi gets overconfident and returns to Boston, where he's immediately arrested. The gig is up for him, though he still seems unerringly confident that the FBI has his back.
    • As for Bulger, he had picked up his girlfriend Catherine Greig and hit the road to parts unknown. There are reported sighting of him "in the Midwest, Florida, and even Mexico" (3.18.65).
    • Bulger never contacts Flemmi again, but he does pay a call to John Morris in 1995.
    • His message is classic Bulger: if Bulger's going down, he's taking Morris down with him.
  • Chapter 19

    In for a Penny, in for a Pound

    • It's 1996, and Cadillac Frank and a Mafioso named Bobby DeLuca are stuck side-by-side in "the Plymouth County Correctional Facility" (3.19.1)
    • Both men have been given a recording by their mutual attorney, Anthony M. Cardinale, long-time mob lawyer.
    • The recordings are from the government's secret wiretap, and Cardinale wants them to see if anything sounds fishy enough to get the tapes thrown out in court.
    • After poring over the tapes, the two men realize that they can hear the whispers of several FBI agents, which means that the FBI lied to the judge about the form of electronic surveillance that they were using.
    • Don't worry about the details, just know that this might mean the tapes are not admissible in court. That's score one for Cardinale.
    • Cardinale has also figured out that the police had an informant in the room when they were recording, which would further poke holes in the government's argument.
    • So he files a motion to force "the disclosure of the identity of various individuals" who served as informants for the case (3.19.23).
    • Could this mean what we think it means?
    • Cardinale openly references Bulger, but doesn't mention Flemmi, as Flemmi is also a defendant in the case and Cardinale doesn't want to tip his hands too early.
    • Despite personally hating Bulger, Wyshak is left in the enviable position of fighting back against Cardinale's request.
    • Eventually, Judge Wolf gives in, and agrees to reveal the potentially explosive information in court.
    • And so, in 1997, Paul Coffey from the US Justice Department finally reveals what Boston has long suspected: Bulger has been an informant for the FBI for decades.
    • Well, we sure hope you're a fan of felines, because this cat is officially out of the bag.
  • Chapter 20

    The Party's Over

    • In 1998, the court officially begins its inquiry into whether the FBI's protection of Flemmi should exempt him and the other gangsters from prosecution.
    • The hearing lasts for almost a year, and the witness list contain tons of characters we already know, like Nick Gianturco and Dennis Condon—though Jeremiah O'Sullivan is suspiciously absent.
    • Theresa Stanley, broken-hearted by Bulger, testifies against her former boo.
    • Similarly, Cadillac Frank is disgusted with Flemmi as he learns about how his so-called "friend" had betrayed him time and time again.
    • Morris testifies in April, having "negotiated immunity" in exchange for his assistance (3.20.32). He's open about his own failings, but doesn't admit to offering immunity to Flemmi and Bulger.
    • As his name continues popping up in court, Connolly turns to the press, shouting into every microphone he can see about how he's been framed.
    • Of course, when he is called into court, he simply pleads the Fifth Amendment (the right to not incriminate oneself) and calls it a day.
    • Because that's how an innocent person acts.
    • When Flemmi is brought up to the stand, he often seems confused. He still can't understand why he's here: the FBI told him he was a cool dude.
    • He does lie in court, however, claiming that Morris told him that he was about to be indicted back in 1995, when in fact it was Connolly who had spilled the beans.
    • Connolly continues his full-court media press.
    • While he doesn't deny his relationship with Bulger, he claims that everything was done above board, and ultimately benefitted the city.
    • He even claims that he has nothing to hide—he'd gladly testify in court. And then, of course, when he's called to the stand, he pleads the Fifth until he can't think straight once again.
    • The final ruling isn't revealed until 1999, just months after "the FBI announced that the fugitive Whitey Bulger was finally being added to its Ten Most Wanted List" (3.20.140).
    • The ruling runs an incredible 661 pages. In it, Judge Wolf eviscerates the FBI for its conduct involved Bulger.
    • In fact, more of the ruling is about Bulger than its nominal subject: racketeering crimes.
    • Everyone is now exposed.
    • There's just one thing keeping this from being a perfect, fairytale ending: Whitey Bulger is still on the run.
  • Epilogue

    • We're not done yet, folks.
    • Connolly is quite displeased when the court ruling is made public, and thus continues his full-on assault on the media, proclaiming his innocence even more loudly than before.
    • Three days before Christmas in 1999, however, Connolly is busted by the FBI.
    • He's charged with engaging in conspiracy and obstructing justice. Finally.
    • At the same time, a host of gangsters, including Cadillac Frank and Kevin Weeks, decide to become informants themselves and give the police information of several murders they committed on behalf of Bulger and Flemmi.
    • In 2008, Connolly is charged as an accessory to murder, with both Morris and O'Sullivan testifying against him.
    • This is huge—everyone is shocked that the court is actually going this far.
    • Of course, Fred Wyshak is the prosecutor.
    • Boston is reeling from these revelations, especially because the Bulger family is so prominent. Jackie Bulger, Whitey's little bro, is convicted for keeping in contact with him while he's on the run, and Billy is accused of the same thing, though he evades punishment.
    • But where in the world is Whitey Sandiego?
    • In 2011, the FBI launches a publicity blitz for the America's Most Wanted List, where Whitey has landed a lucky spot.
    • And it works. Whitey and Catherine Greig are discovered in Santa Monica, California, where they've been living under assumed identities as an old retired couple.
    • In a hilarious twist, the police were tipped off by the couple's neighbor, who recognizes Greig as the woman who always feeds local stray cats.
    • And they would've gotten away with it too if it wasn't for those meddling felines…
    • Whitey is rushed back to Boston and immediately made to stand trial.
    • It might have taken a few decades too long, but we can finally rest easy knowing that Whitey "would never again draw a breath as a free man" (e.77).