Whitey Bulger: Crime Boss, Rat, Fugitive

Mob boss James “Whitey” Bulger ran Boston’s underworld with an iron fist for decades. As his empire grew, his enemies fell. He was seemingly untouchable. For a gangster of his stature, that kind of longevity was extraordinarily rare. So how on earth did he stay out of handcuffs for so long? Help us reach 10k followers on Instagram! @⁠theconspiracypod⁠ Learn more about your ad choices. Visit podcastchoices.com/adchoices

• 0:06Speaker 00

  It's January 1995, and Whitey Bulger, one of the most infamous mob bosses in American history, is on the run. As always, he seems to be one step ahead of law enforcement. You see, he has a man inside the FBI. That man, an agent named John Connally, has tipped him off. Whitey is about to be indicted on racketeering charges. Those include extortion, narcotics distribution, and a murder. At the time, the gangster and his girlfriend, Teresa Stanley, are driving home to South Boston from a vacation in New Orleans. When Whitey hears that there's a warrant out for his arrest,

• 0:49Speaker 00

  he turns his car around and heads to a hotel somewhere in New England. He hides out there for a few days and plots his next move. This is not Whitey's first rodeo. As a younger man, he'd served a long stint in federal prisons for bank robbery. He doesn't want to go back to jail. This time, he has an alias ready: Thomas F. Baxter. Now, the real Thomas F. Baxter, who lived in suburban Boston, died in 1979, and Whitey assumed his identity. He even secured a Massachusetts driver's license with his own photo, using Tom's birth date and social security number.

• 1:32Speaker 00

  Whitey's crafty. He can handle life on the lam. His traveling companion, well, can't. So he drops Teresa off at a Chili's restaurant in Hingham, Massachusetts. Ah, but don't worry about Whitey. He won't be a lonely fugitive. After parting ways with his girlfriend, he picks up his mistress. She's a dental hygienist named Catherine Greig. They've been having an affair for a decade. On January 17, 1995, Whitey buys a new Mercury Grand Marquis in Selden, New York, in Tom Baxter's name, then he and Catherine go south. This is the start of Whitey's odyssey.

• 2:16Speaker 00

  And despite being on the FBI's most-wanted list, he manages to evade capture for 16 years. But before sneaking away, Whitey calls his younger brother, William. Their phone conversation only lasts a few minutes, but Billy has a message for Whitey. "It's not in your interest to surrender to the authorities." On the surface, well, there's nothing abnormal about that exchange. But Billy Bulger, an attorney by trade, isn't an ordinary citizen. He's the president of the Massachusetts Senate. That's right. Whitey's little brother, Billy, is arguably the most powerful politician in the state.

• 2:59Speaker 00

  Billy later tells a federal grand jury that he's loyal to his brother. He also says this: "It's my hope that I'm never helpful to anyone against him. I don't feel an obligation to help everyone to catch him." Eventually, Whitey does get caught, though for a long time, he's untouchable. Before his indictment in 1995, he hadn't faced a single criminal charge in 39 years. Luck always seems to be on his side. But Whitey Bulger's superhuman ability to stay out of handcuffs is, in reality, the product of having an extraordinary amount of help,

• 3:42Speaker 00

  and not just from his allies in the underworld. He builds a criminal empire off the complicity of some of Boston's most powerful people. It must be nice having friends in high places. Welcome to Conspiracy Theories, a Spotify podcast. I'm Carter Roy. New episodes come out every Wednesday. We would love to hear from you. So if you're listening on the Spotify app, swipe up and give us your thoughts, or check us out on Instagram at the conspiracy pod. This episode includes discussions of violence, murder, death, sexual abuse, and drugs.

• 4:24Speaker 00

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• 6:13Speaker 00

  To a lot of Bostonians, Whitey Bulger is a folk hero. Well, he might be capable of violence, but he's loyal, and he protects his own. People even claim that he's driven the drug trade out of South Boston, his Irish-American neighborhood. Until not that long ago, ordinary citizens in his neck of the woods spoke highly of Whitey. In a man-on-the-street interview from 2013, here's what someone from Southie offers up about him: "He was good friends with my grandfather and my grandmother. He always helped us out if anything needed." All of this perception about Whitey is, of course, a myth. He's more like Al Capone than Robin Hood. His brutal reign lasts decades.

• 6:57Speaker 00

  To Dick Laer, a journalist who's co-written two books about the kingpin, that longevity is what makes him unique. Here's what he says about Whitey: "Check out how long John Dillinger was around. I don't think anybody had the ride that Whitey had." How exactly does Whitey stay on top for so long? Well, almost every move he makes is out of self-interest. He builds his empire by ruthlessly exploiting his connections to politicians, local cops, and federal agents, cross him, and risk getting hurt, or worse. He shakes down lesser criminals, bribes public officials, rats out his competition, and kills rivals with impunity,

• 7:41Speaker 00

  all while keeping up the image of an anti-hero. But that is bunk. In Whitey's world, there is no honor among thieves, even if that's what he wants you to believe. He relies on his reputation as a noble, tough guy. It's a rep he earns at a young age. Ah, okay, well, maybe not the noble part. James Joseph Bulger Jr. is born on September 3, 1929, in Dorchester, the biggest neighborhood in Boston. His father, a laborer who lost part of his arm in a rail yard accident, is unable to work full-time. He and his wife Jean have six children. In need of an affordable and roomy enough place to live, the family soon moves to Southie.

• 8:25Speaker 00

  They live in Old Harbor, New England's first housing project. Junior likes to go by Jimmy, but his blond hair leads to a nickname: Whitey. He hates it. He's known as a polite child at home. His mother runs a tight ship. But let's just say he's, well, not as studious as his brother Billy. As a boy, Whitey joins a gang, learns how to steal cars, and beats people up. His behavior gets him sent to reform school. At 20, he enlists in the Air Force, but he goes AWOL and ends up getting discharged. Then he starts robbing banks and is caught. In 1956, he's sent to federal prison. Whitey serves the early years of his sentence

• 9:10Speaker 00

  at a penitentiary in Atlanta. In exchange for a slight reduction in jail time, he agrees to participate in a clinical trial.

• 9:20Speaker 00

  Is a doozy. See, Whitey is part of a small group of inmates that the CIA doses with LSD. The agency wants to study how the men react to the psychedelic drug. Whitey tells his brother Billy about the program in a letter. It worries Billy, who later says this. There were only eight to 10 of them, and two guys went stark, raving mad. You couldn't go through something like that and come out improved. If you've listened to one of our episodes about MKUltra, the CIA's attempt to master mind control, this scenario might sound familiar. Whitey ends up suffering from nightmares into middle age.

• 10:04Speaker 00

  He believes they're caused by the LSD experiment. In 1959, Whitey is transferred to Alcatraz, then Leavenworth, then Lewisburg, Pennsylvania. While doing time, he works out, reads, and studies warfare, all things to help prepare him for navigating Boston's underworld. In March 1965, he gets released from prison and goes home to South Boston. Whitey is afraid of violating his parole, so he tries to go straight. Billy, who by then is a Massachusetts state representative, gets his brother a job as a janitor in a courthouse. His tryout as a law-abiding citizen doesn't last long, though.

• 10:48Speaker 00

  In the 60s, Whitey returns to a life of crime. Hey, pays better than mopping floors. Whitey works as an enforcer for the three Colleen brothers, who run a gambling ring and loan sharking operation in Southie. In the early 1970s, the Colleens are challenged by the rival Mullins gang. Whitey reportedly protects his bosses for a while. But then Whitey starts to feel underappreciated by Donnie Colleen, their leader, so he decides to switch teams. On May 13, 1972, Donnie is sitting in the front seat of his car when a machine gun-wielding

• 11:29Speaker 00

  assailant approaches and pumps 15 bullets through the window. Donnie is dead. The police suspect Whitey was involved, but no one is ever charged with the murder. And Whitey claims he had nothing to do with it. The killing and others linked to him help boost Whitey's reputation among Boston's gangsters. Even if he's not responsible for all the pain he's rumored to have inflicted, he's not someone to mess with. When it comes to Whitey Bulger, the legend often becomes fact. Whitey is the keeper of his own myth. He's also shrewd.

• 12:10Speaker 00

  He understands that to climb the criminal ladder, he has to make alliances and also not be afraid to break them when it serves him. Just ask the surviving Colleen brothers, because Whitey's loyalty is, well, flexible. His professional relationships are usually built on cynical foundations. In the early 70s, the police notice that he started to show up at a garage up the road in Somerville. It's the headquarters of the Winter Hill Gang, a group of Irish mobsters that works parallel to the Italian mafia. Now, this is where Whitey first partners with Stephen Flemmy. Flemmy's nickname, The Rifleman.

• 12:55Speaker 00

  Oh, and one of Stephen's brothers is a Boston cop. Whitey is Irish. Stephen is Italian, but they work together. They're smart. They don't bite off more than they can chew, and they protect their turf instead of trying to amass more of it. But here's where I need to remind you again that Whitey is not, by any stretch of the imagination, benevolent. I'm jumping ahead a little bit here, but he's eventually charged with 19 murders. The victims include rival gang members and a co-conspirator who he's afraid will rat him out. In 1973, a local bartender named Michael Milano is shot to death in a case of mistaken identity.

• 13:41Speaker 00

  He allegedly drove the same kind of car as the intended target of the hit. In 1974, that mobster is also killed, and Whitey is linked to that murder, too. By then, it's safe to say that Whitey has become a force to be reckoned with. You could say the same thing about his brother Billy. In 1970, after serving five terms in the Massachusetts House of Representatives, he's elected to the state senate. The Democrat serves the first Suffolk district, which is home to Southie. In the mid 70s, the Bulgers' neighborhood is in tumult. It is ground zero for the controversy surrounding court-ordered desegregation of the Boston school system.

• 14:24Speaker 00

  Some residents are outraged that their children will be bused to Roxbury, a mostly black neighborhood. They're also angry that children from Roxbury will be bused to Southie. Things get ugly. Activists and citizens spew racist rhetoric on the day the policy goes into effect. White teenagers outside South Boston High School throw bottles and rocks at black students. Billy Bulger is publicly against busing. He claims outsiders shouldn't have a say in how his constituents live. To him, it's unfair that his community is being forced to bear the burden of the new law.

• 15:05Speaker 00

  He calls police officers who arrested white protesters in Southie "the Gestapo." At one point, he confronts Robert DeGrazia, Boston's police commissioner, and says this. "The community has a message for you. Go [bleep] yourself." Like his brother Whitey, Billy understands the importance of loyalty, or at least the appearance of it. His ultimately failed stand against busing gains him even more support in South Boston, even if it hurts him elsewhere. Whitey opposes busing himself, but during the crisis, he personally waves Southie's

• 15:47Speaker 00

  hoodlums away from the protests, not because he cares about keeping the peace, but because more chaos likely means more police. And the last thing he wants is law enforcement interfering with the criminal empire he's building. Somehow, even with all the heat on Southie, Whitey manages to stay clean. It's remarkable, but how? The answer to that question can be found in the best deal he's ever made, an unholy alliance that changes Whitey and Boston forever.

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• 17:26Speaker 00

  It's a clear night in the fall of 1975. FBI Agent John Connolly parks his Plymouth near a beach in Quincy, Massachusetts, and waits nervously. All of a sudden, the passenger door pops open, and someone gets in. It's Whitey Bulger. John has requested this meeting. He wants to recruit Whitey as an informant. He's 11 years younger than the gangster, but they grew up in the same housing project in Southie. As a child, he'd heard stories about Whitey's toughness and looked up to Billy. When John was eight, he walked into a drugstore and heard his friends whisper, "There's Whitey Bulger."

• 18:10Speaker 00

  Whitey, by then in his late teens, offered to buy the grade schoolers ice cream. John turned down the offer, but then Whitey assured him that he's no stranger. He also reminded him that their parents are all from Ireland. John changed his mind and accepted a vanilla cone. Later that year, John got into a fight over a ball. Almost magically, Whitey showed up and shooed the other kids away.

• 18:37Speaker 00

  After high school, John took Billy Bulger's advice and attended the politician's alma mater, Boston College. In 1968, John joined the FBI, and in 1973, he transferred from the New York office to his hometown branch. By the mid-'70s, the FBI has already tried to cultivate Whitey as a source. Didn't seem to work, but John figures his personal connection will help bring Whitey on board. Hey, they knew each other, and they even grew up in the same neighborhood. John's pitch appeals to Whitey's extreme self-interest. Now, back then, the mobster is still associated with the Winter Hill Gang.

• 19:20Speaker 00

  That outfit is about to go to war with a local Italian mafia, which is run by Jerry Angiulo. Now, what's the beef about? The vending machine business. John claims that Angiulo is already ratting out Whitey and the Winter Hill Gang to the Boston cops, so John's proposition is to fight fire with fire. If Whitey and his right-hand man, Stephen Flemmy, feed the Bureau information about the mafia, that will help bring the Italians down. They'll eliminate Whitey's competition. In exchange, the FBI will look tough on organized crime. Oh, one more very important thing is part of the agreement.

• 20:05Speaker 00

  The FBI will lay off Whitey and his crew. That's right, the local branch of the top law enforcement agency in the country is getting into bed with a suspected murderer. It is bonkers. When the deal is cemented, Whitey says to John that the mafia will be playing checkers, and he'll be playing chess. By the late 1970s, the FBI is clearly protecting Whitey. At one point, he and Stephen allegedly threaten to kill a restaurant owner if he doesn't pay off a loan. Local police look into the matter, but the FBI squashes it. Around this time, the Winter Hill Gang is the target of a horse race fixing probe.

• 20:48Speaker 00

  Whitey and Stephen are implicated, but claim innocence. At the time, Connolly's supervisor at the FBI is John Morris. He's the head of Boston's organized crime unit. Morris convinces Jeremiah T. O'Sullivan, the federal prosecutor on the case, to remove the duo from the coming indictment. Connolly later says that the prosecutor grants the request on one important condition: that Whitey and Stephen agree not to murder the government's top witness. Oh, not kill the guy, and we get off scot-free. I'm gonna have to check. Are we? Yeah, I guess we can do that. Yeah, they, uh, they comply.

• 21:31Speaker 00

  Twenty-one people are indicted in the race fixing scheme. One is Howie Winter, the leader of the Winter Hill Gang. He gets convicted and sent to prison for a long stretch. His successor, oh, look at that, none other than Whitey Bulger. Whitey is now the boss of Boston's Irish mob, and the local branch of the FBI doesn't seem to mind. Connolly takes his fellow agents to dinners with Whitey and Stephen. The Bureau bans taking gifts, but they exchange presents at Christmas time anyway. Oh, and by the way, Connolly's old friend Billy Bulger attends at least one of these gatherings.

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  Morris, Connolly's boss, even hosts dinners for Whitey and Stephen. He also starts taking payoffs from them. At one point, Morris tips the pair off about the state police bugging their parking garage on Lancaster Street near Boston Garden. It's clear what Whitey gets out of his deal with the FBI, but what does the FBI get out of it? By 1980, that's what the Bureau is trying to figure out. There are well-founded rumors that agents are in way too deep with Whitey. Lawrence Serhat, the new special agent in charge of the Boston office, is worried. He's heard about the parking garage leak, which royally pisses off the state police,

• 22:57Speaker 00

  and wants to cut ties with the mobster. Naturally, this ends Connolly and Morris scrambling. They have tied themselves to Whitey, and now they have to prove they have something to show for it. They start sending memos to their supervisors about Whitey's importance to the case they're still building against Jerry Angiulo and the mafia. In one of his reports, Connolly claims that Whitey had heard about his garage being bugged from a source in the state police, not from Morris, which is a complete lie. Morris also springs into action. He orders his two high-profile informants to find out if Jerry Angiulo's headquarters on Prince Street in the North End is protected by an alarm system.

• 23:42Speaker 00

  If it is, that would make it harder for the FBI to gain entry and install listening devices. The duo comes back with a diagram of Jerry's office, but nothing about an alarm. Somehow, that's enough for the FBI to designate Whitey and Stephen as informants in a sworn affidavit. That affidavit convinces a judge to OK a wiretap. The move saves Whitey's job as an informant, but Serhat, the new boss, still isn't convinced that the FBI should be hitching its wagon to a violent criminal, so he calls Whitey to the Logan Airport Hilton for a chat.

• 24:24Speaker 00

  When Serhat gets there, the mobster appears relaxed and confident, even puts his feet up on a coffee table. During the conversation, which lasts four hours, Whitey repeats the lie that someone with the state police, not the FBI, told him about his garage being bugged, but he refuses to disclose the name of the source. That's a breach of protocol. Still, Connolly, Morris, and O'Sullivan, the federal prosecutor, end up pushing Serhat to keep Whitey on as an informant. O'Sullivan calls Whitey crucial to the investigation. The FBI does go on to build a strong case against Angiulo, who runs a lucrative loan

• 25:07Speaker 00

  sharking and gambling operation, but it's really no thanks to Whitey. In reality, the true source of incriminating information about Angiulo is a local bookmaker. This bookie knows how and where the city's illegal gambling money is being delivered. He shares that info with the feds for one simple reason: Angiulo is screwing him over financially. Acting on the bookie's tip, FBI agents plant microphones in the ceiling above Angiulo's office. Starting in early 1981, the feds monitor the recordings, and this helps lead to the downfall of the Angiulo crime family. Jerry is arrested in 1983, eventually convicted of racketeering, and he spends 21 years

• 25:52Speaker 00

  in prison. By then, the FBI's protection of Whitey becomes almost laughably transparent. After agents bug Angiulo's office, Connolly and Morris write a memo claiming that Whitey has indeed helped build a case against the mafia. In their note, they also write that "the Winter Hill Gang is dead," and, I quote, "does not merit further targeting at this time or any time in the foreseeable future." It is totally ridiculous. The crackdown in the late '70s thinned its ranks, but the Winter Hill Gang still exists.

• 26:32Speaker 00

  Whitey's in charge of it now, and with Angiulo out of the picture, he and Flemmy start grabbing more and more turf. Like the mafia before them, they skim profits from bookies and drug dealers, and they rely on their underlings to collect for them. Whitey is anything but loyal. He doesn't just rat on his rivals to keep the FBI happy. He feeds Connolly bits of information on people in his own gang. Boston mobsters: Howie Winter, Pat Nee, Joe Murray, Jimmy Sims, and Joe McDonald all end up getting busted. Whitey gives Connolly info on all of them.

• 27:15Speaker 00

  In the '80s, Whitey is Boston's version of the Teflon Dawn. Nothing seems to stick to him despite his many misdeeds. For example, in 1983, he and Flemmy are out and about in South Boston when they notice a nicely renovated store. It doesn't matter that Stippo's Liquor Mart isn't for sale. They want it, so they pay a home visit to the co-owner, Stephen Rakes, hand him $67,000 in cash, and tell him that the store is now theirs. Rakes says that he and his wife Julie don't want to sell their store. In response, Flemmy allegedly lifts one of Rakes' young daughters on his lap and sets

• 27:59Speaker 00

  his gun on the kitchen table nearby. According to federal grand jury testimony, the child picks up the weapon. Whitey, who's watching, allegedly says this to Rakes: "It would be a shame not to see your children grow up." Rakes is terrified. Julie’s uncle, a Boston detective, goes to John Connally to ask for help, but Connally does nothing to stop the takeover. He claims that he can’t do anything if Stephen and Julie Rakes refuse to be witnesses against Whitey. Officially, Stippo’s Liquor Mart is sold to a man named Kevin Weeks, one of Whitey’s lieutenants.

• 28:42Speaker 00

  The store is renamed South Boston Liquor Mart. Whitey and Flemmy are spotted there frequently. And when FBI agents need booze for a Christmas party, they stop by the store. Oh, naturally, they get a big discount. The incident is unconscionable, and it’s one of many. The FBI’s corrupt bargain with Whitey costs people their lives. In 1982, a Winter Hill gang associate named Brian Halloran, an accused murderer, tells the Boston FBI he wants to be a cooperating witness against Whitey and Flemmy. He believes they want to kill him.

• 29:24Speaker 00

  Halloran approaches the FBI and says that he can provide information on two murders Whitey allegedly had a hand in committing. Like clockwork, John Morris proceeds to tell Connally that Halloran is conspiring against Whitey and Flemmy. Connally then lets Whitey and Flemmy know that Halloran is ratting them out. It is hard to believe that Morris and Connally don’t know what will happen next. Because you probably guessed it, as he’s leaving a bar in South Boston on May 11, 1982, Halloran dies in a hail of gunfire. He knew too much, and he paid the price.

• 30:07Speaker 00

  And there was nothing anyone was going to do about it. By now, it should be pretty obvious. Whitey Bulger is a violent criminal. But even while he’s wreaking havoc on Boston, myths about him persist. These myths fool the public, or at least a segment of the public, into thinking that he’s not purely a villain. So what are some of those myths? The most pervasive tall tale about Whitey is that he kept illegal drugs out of South Boston. It is not true. The drug trade existed in Southie.

• 30:49Speaker 00

  Whitey may not have been handing out bags of cocaine himself, but he and his cronies charged dealers’ rent for selling on his turf. Back in the 80s, a local dealer says this to an undercover DEA agent: “You either pay Whitey Bulger, or you don’t deal, or you wind up dead.” A second myth is that Whitey only killed people who were a threat to him, and never women. Again, it is not true. In the mid 80s, Whitey becomes worried about the behavior of a young woman named Deborah Hussy. She’s the grown daughter of Flemmy’s girlfriend. Deborah has had a difficult life.

• 31:34Speaker 00

  When she’s 16, Flemmy allegedly sexually abuses her. In her 20s, Deborah uses drugs and spends time at Triple O’s, a bar in South Boston where Whitey hangs out. Flemmy will later testify that Whitey decides they should kill Deborah. Why? Because to Whitey, she’s an embarrassment. One night in January 1985, Flemmy brings Deborah to a house in Southie and takes her into the basement. Whitey is waiting. He steps out from behind the stairs and strangles Deborah to death. Whitey, Flemmy, and Weeks bury her under the floor.

• 32:15Speaker 00

  It is unbearably cruel. A third myth, and the most absurd of them all, is that Whitey isn’t actually an informant. At least publicly, he denies that he ever worked with the government, probably because in his world, snitching is an abomination. But over and over, he breaks the code of the street. Here’s how the father of one of Whitey’s murder victims puts it: “A lot of these people looked up to Bulger like he was some hero. To find out that he was an informant, and ratting people out, and killing people, and getting away with it, it makes him look like the scum that he is.”

• 33:00Speaker 00

  For a long time, Whitey keeps getting away with just about everything. And law enforcement keeps letting it happen. In 1983, a detective in Quincy named Richard Bergeron is planning an investigation. He’s looking into whether Whitey and Flemmy are extorting drug dealers. Operation Beans is a team effort. The Quincy PD, the DEA, the state police, and the US Attorney’s Office are in on it. Bergeron is not naive. He knows taking on Whitey will require precision and discretion. But once again, meddling by the FBI allegedly makes that impossible.

• 33:42Speaker 00

  Morris, Connally’s boss, later says that when an investigation is about to come down against Whitey and Flemmy, the two men are often tipped off. In 1984, someone in the Boston FBI office sends an anonymous memo to the Bureau’s HQ in Washington. The note details the probe of a drug trafficking operation controlled by the Irish mob. The same note also tries to throw the national office off the scent by claiming that the DEA has no specific information about Whitey’s involvement in that particular operation. The US Attorney’s Office still gets approval to wiretap Whitey.

• 34:27Speaker 00

  The DEA even bugs his car. But curiously, he doesn’t seem to say anything incriminating on tape. A few days after the recording device is planted, Whitey finds it. In March 1985, Stephen Borey, the DEA agent listening in, retrieves the equipment. Whitey teases Borey and his colleagues, saying he’s impressed that the DEA got around his car alarm. The federal prosecutor working the case says he never figured out why the investigation failed, but in his mind, it had clearly been compromised. After Operation Beans fails, Borey sarcastically sends Whitey and Flemmy a congratulations card.

• 35:11Speaker 00

  He also gives both cigars. It’s his way of courting them as DEA informants. He has no idea that the FBI had beaten him to the punch a full decade before that. Even with the FBI putting up roadblocks, local law enforcement doesn’t give up trying to bring down Whitey. In 1989, Boston detective James P. Carr writes a well-sourced affidavit concluding that anyone running illegal businesses in Southie must hand over a cut of their profits to Whitey. Then there’s Bonnie Alexander, an undercover DEA agent who buys coke from a dealer named Thomas Cahill.

• 35:54Speaker 00

  He won’t shut up about Whitey’s involvement in the drug trade. The investigation is fruitful. In 1990, 51 people are indicted on drug charges. The DEA is happy with the sweep. Many of the dealers and enforcers caught up in it work under Whitey, but there apparently isn’t enough evidence to arrest Whitey and Flemmy. There may be a reason for that. The FBI takes a witness willing to testify against Whitey and uses him in a different investigation. This helps keep Whitey safe, but only for a little while longer. By then, Whitey’s days as the FBI’s darling are practically over.

• 36:37Speaker 00

  In the late 80s, Morris grows tired of being in cahoots with the head of the Irish mob. He advises the feds to dump Whitey as an informant. But Whitey sticks around, because now, there’s a new special agent in charge of the Boston Bureau. And James Ahern buys into Connally’s version of Whitey. In a memo to “the Director of the FBI,” Ahern calls Whitey, and I quote: “The most important organized crime informant for many years.”

• 37:12Speaker 00

  But Connolly can't sell that lie forever. It's Flemmy, not Whitey, whose tip leads to an FBI first, bugging a mafia induction ceremony. In 1988, The Boston Globe reveals the connection between Whitey and the FBI. A heron tells the paper that it's not true, but soon Connolly is barred from hosting Whitey at his home, and Flemmy and Whitey are dropped as informants. It's taken decades, but Whitey is finally taking some hits. But someone still has to deliver the knockout blow. Enter Fred Wyshak Jr., a new prosecutor in the US Attorney's Office.

• 37:56Speaker 00

  He cut his teeth in Brooklyn and New Jersey before transferring to Boston. As anyone who's from there will tell you, the city is a provincial place. It takes an outsider to crack Whitey. And in the early 90s, Fred is on a mission. Instead of gunning for the big bust, he takes a methodical approach. At the time, local bookmakers are paying up to Whitey. The penalty for a gambling charge tends to be a fine and maybe a short stint in jail. Then Fred changes the game. He starts to add money laundering to gambling charges. That can lead to real prison time.

• 38:38Speaker 00

  The strategy is to scare the bookies into testifying against Whitey, stay silent about the extortion payments to Whitey, and risk facing hard time. The ploy works. In 1991, the state police flipped the head of New England's biggest gambling ring. His name is Burton Chico Krantz. Acting on info gathered from wiretaps all the way back in the 80s, chalk it up to fresh eyes, law enforcement pursues Chico to be an informant. He admits to kicking up to Whitey and Flemmy. Still, it takes several more years to build a viable case against Whitey.

• 39:20Speaker 00

  As the walls slowly close in, John Connolly realizes that he's in too deep. He's so afraid of what his former informant might do that Connolly becomes a cooperating witness against him. For a while, Connolly even supposedly wears a wire. He retires from the FBI in 1990 and takes a big job at Boston Edison, a job he's rumored to get with the help of his friend, Billy Bulger. In early 1995, the indictments of Whitey and his associates finally materialize. Boston cops find Flemmy in his Honda on Broad Street and draw their guns on him. He surrenders peacefully.

• 40:04Speaker 00

  But Whitey knows nowhere to be found. John Connolly has tipped him off. Billy Bulger, who's still the president of the Massachusetts Senate, doesn't seem interested in helping track down his brother. Billy talks to Whitey on the phone in January 1995. The conversation is arranged by Kevin Weeks, Whitey's lieutenant. Billy doesn't tell law enforcement about it, later saying, and I quote, "That was somewhat protective." By now, Whitey has bolted. The gangster, who's in his late 60s and his partner Catherine, who's in her late 40s, adopt aliases and travel the country.

• 40:46Speaker 00

  There are Whitey sightings in New York, Mississippi, and Wyoming, but law enforcement can't seem to get the drop on him. For a stretch in the mid 90s, the fugitives hide out in Grand Isle, a remote resort town in Louisiana. Their neighbors know them as New Yorkers named Tom and Helen. They grow very close to one couple, Penny and Glenn Gattrow. Whitey buys gifts for their family, fancy dinners, new appliances, and toys for their kids. Law enforcement traces Whitey and Catherine to Grand Isle in 1997, but by then, they're long gone. Penny is subpoenaed to appear in front of a federal grand jury about her connection to Whitey.

• 41:31Speaker 00

  Even after learning his true identity, she doesn't disavow him. In fact, she resents having to testify. Here's what she says about the FBI. "I figured they made it bigger than what it is. Really, I hate them more than him." It is yet another story of Whitey manipulating someone into thinking that he's not actually a monster. He knows that loyalty has a price. Eventually, though, Whitey can't buy his way out of trouble. While he's on the run in the 90s, the dominoes begin to fall. Court hearings for Flemmy, who's facing racketeering and extortion charges, expose

• 42:14Speaker 00

  years of rampant FBI corruption. Flemmy claims that when he and Whitey were working as informants, they were allowed to commit crimes, just not murder. The judge disagrees, ruling that the two gangsters were never actually given that kind of immunity. Flemmy agrees to a plea deal in 2001 and is sentenced to 10 years in prison, but that's just the tip of the iceberg. Evidence of his most heinous crimes is piling up. To avoid the prospect of the death penalty, Flemmy pleads guilty to 10 counts of murder and is sentenced to life in prison in 2003.

• 42:56Speaker 00

  Kevin Weeks, who's been running the ship for his boss and sending him money when he's on the lam, gets arrested on federal racketeering charges in 1999. Instead of risking a trial that could send him to prison for the rest of his life, he decides to turn against the kingpin, and he does so in dramatic fashion. Kevin leads law enforcement to the bodies of eight of Whitey's alleged victims. John Connolly, who enabled Whitey for decades, gets his comeuppance, too. He's arrested in 1999 on a list of federal charges that should sound familiar: tipping

• 43:40Speaker 00

  Whitey and Flemmy off to investigations against them, falsifying reports, and taking bribes. Connolly is later charged with giving information to Whitey and Flemmy that led to the murders of a witness and two FBI informants. Connolly is already in prison for racketeering when he's convicted of second-degree murder in 2008. He's sentenced to 40 more years. Billy Bulger's ties to his fugitive brother also finally catch up to him. When a congressional committee calls him to testify about Whitey and the FBI's alliance in 2002, he pleads the Fifth.

• 44:22Speaker 00

  The next year, he's hauled in front of the US House of Representatives to answer questions. For six hours, Congress grills Billy, who's now making almost 360 grand a year as president of the University of Massachusetts. Billy admits talking to Whitey on the phone in January 1995. Beyond that, his strategy seems to be deny, deny, deny. He denies knowing that his brother was engaging in criminal activity. He denies that he and Connolly worked together to protect Whitey, and he denies knowing where Whitey is. Here's what he says. "I have not aided James Bulger in any way while he has been a fugitive.

• 45:05Speaker 00

  Do I possess information that could lead to my brother's arrest? The honest answer is no." So where on earth is Whitey? He and Catherine have settled down far, far away from Boston. They live in Unit 303 at the Princess Eugenia Apartments in Santa Monica, California. Their neighbors know them as Charlie and Carol Gasko now. For a while, they almost seem to have a normal life, at least for a couple on the lam. On May 1, 2011, Whitey is watching when President Barack Obama announces on live television

• 45:48Speaker 00

  that the US has killed Osama bin Laden. To the mob boss, this is both good and bad news. He's happy bin Laden is dead, but now he's back on top of the FBI's most-wanted list.

• 46:04Speaker 00

  Soon, Whitey is ready for war. He has an array of guns and plenty of cash stashed in the apartment. He isn't going to let anyone take him alive. Well, the FBI has its own plan. The Boston Bureau films a TV commercial that focuses on Catherine. The 32nd Public Service Announcement includes photos of her. The narrator tells viewers that she's harboring a fugitive, Whitey Bulger. The ad also promises a $100,000 reward. In June 2011, the spot airs around the country during daytime talk shows. Networks across the world pick up the story and then the tips start rolling in. One in particular piques the FBI's interest.

• 46:49Speaker 00

  It comes from Anna Bjorn's daughter, an Icelandic woman who lives in Santa Monica. She says that she thinks Catherine and Whitey, that is Carol and Charlie, live in her apartment complex. Anna and Carol are friends. She says that Carol is very pleasant and that Charlie is a racist. She also notices that Charlie, who claims to be from Chicago, has a Boston accent. Agents trace the names Carol and Charles Gasko to Santa Monica, but there's no more information about them beyond their address. That's because they don't really exist.

• 47:29Speaker 00

  Scott Gariola, an FBI special agent based in Los Angeles, has heard a lot of tips about Whitey over the years, but this one feels more credible than most. So on June 22, 2011, he and a team of agents head to the Princess Eugenia Apartments. Scott shows Josh Bond, the building manager, photos of the fugitives. Josh says, yes, they live here. When Scott explains who they really are, Josh can't believe it. Scott then calls LAPD for backup to lure Whitey out of his apartment. Scott gets creative. He uses bolt cutters to snip the lock off the Gasko's storage unit.

• 48:13Speaker 00

  Then he has Josh call Carol and Charlie and tell them that their locker has been broken into. Sure enough, Charlie, Whitey, takes the elevator down to the garage. Agents are waiting for him there with guns drawn. They tell him to get down on his knees, but he refuses. There's a pool of oil nearby. Whitey, it seems, doesn't want to get dirty, so he takes a few steps and puts his hands up. Scott then asks his name. Whitey's reply, "You know who I am." Scott puts Whitey in handcuffs. After 16 years on the run, he's taken into custody.

• 48:55Speaker 00

  During his federal trial back in Boston, Whitey remains defiant, even as his former partners in crime testify against him. On the stand, Kevin Weeks sticks the knife in, verbally. He says this about Whitey and Flemmy, "We killed people who are rats, and the two biggest rats were sitting right next to me." When Whitey hears that, he blurts out, "Fuck you!" The judge scolds him. Until the end, Whitey's defense team maintains that despite all the evidence, he's not a rat. Fred Wyshak, the US Attorney, calls BS on that assertion, saying this, "Unless it is

• 49:35Speaker 00

  Mr. Bulger's contention that all of these agents got together to fabricate this file for some reason, his contention that he was not an FBI informant is simply absurd." It's not 1980 anymore. Back then, Whitey said that no one would believe that he's an informant. As he put it, "It would be too incredible." But over time, his myth starts to erode, well, at least enough to put him in prison. On August 12, 2013, a jury finds Whitey guilty of having hand in, among many other crimes, 11 of the 19 murders he's been linked to.

• 50:17Speaker 00

  He's 83 and will spend the rest of his life behind bars. In the fall of 2018, Whitey is transferred. He moves from a prison in Florida, known for being safe for high-profile inmates, to a more chaotic lockup in West Virginia. The Hazleton Penitentiary is known for being extraordinarily violent. The day before Whitey is brought there, an inmate named Sean McKinnon calls his mother and tells her that he's heard about the impending transfer of a high-profile prisoner. Among the inmates, Whitey's arrival is an open secret. On October 29, 2018, at 8:30 PM, Whitey is brought into his cell in a wheelchair.

• 50:59Speaker 00

  The next morning, McKinnon and his cellmate, Freddie Gias, meet up with another inmate, Paul J. Decolagüero. McKinnon then sits at a table near Whitey's cell and keeps an eye on the guards. Because the unit doors are unlocked for breakfast, Decolagüero and Gias are able to enter Whitey's cell. With Decolagüero acting as a lookout, Gias repeatedly bludgeons Whitey in the head with a lock attached to a belt. On October 30, at 8:07 AM, the 89-year-old mob boss is found dead.

• 51:39Speaker 00

  Gias, a mafia hitman, and Decolagüero, who's in jail for racketeering, both have ties to organized crime in Massachusetts. Another inmate later tells a grand jury that he'd heard Decolagüero say he was planning to kill Whitey for being a snitch. People who knew Gias say he also, and I quote, "hated rats." He also hated men who hurt women. Whitey checked both boxes. It's still unclear how Whitey's assailants found out that he was coming, but there's reportedly no evidence that prison staff leaked such sensitive information on purpose.

• 52:23Speaker 00

  An investigation by the Justice Department in 2022 finds that no one with the Federal Bureau of Prisons acted with any malicious intent. Instead, the report blames Whitey's murder on "staff and management performance failures, bureaucratic incompetence, and flawed, confusing, and insufficient policies and procedures." In a way, it's ironic. Thanks to the secret deals he made with the FBI, Whitey Bulger acted with depraved impunity for decades. He was untouchable. But in the end, the kind of bureaucratic failures and incompetence that helped protect

• 53:07Speaker 00

  him for far too long also probably helped do him in. Thank you for listening to Conspiracy Series. We're here with a new episode every Wednesday. Be sure to check us out on Instagram, @TheConspiracyPod. If you're watching on Spotify, swipe up and give us your thoughts. Our sources for today's episode include The Boston Globe Spotlight Team's excellent, long-running coverage of Whitey Bulger, and Gerard O'Neill and Dick Laers' book, Black Mass: Whitey Bulger, the FBI, and a Devil's Deal. Until next time, remember, the truth isn't always the best story.

• 53:51Speaker 00

  And the official story isn't always the truth. This episode was written and researched by Alan Siegel, edited by Mickey Taylor, fact-checked by Sophie Camp, engineered by Alex Button, video edited and sound designed by Jamie Yucich. I'm your host, Carter Roy.