In 2015, Scott adapted another book to film. This time it was a book by Dick Lehr and Gerard O’Neill called Black Mass: Whitey Bulger, the FBI, and a Devil’s Deal. Let’s dive into the crime-riddled streets of Boston as we compare history with Hollywood’s version of Black Mass.
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- Black Mass: Whitey Bulger, the FBI, and a Devil’s Deal by Dick Lehr and Gerard O’Neill
- Whitey Bulger’s Enforcer Slams ‘Black Mass’: ‘The Movie Is Pure Fiction’ – The Daily Beast
- Black Mass (2015) – IMDb
- Scott Cooper – IMDb
- Black Mass (2015) – Full Cast & Crew – IMDb
- Black Mass (film) – Wikipedia
- Black Mass (2015) – Rotten Tomatoes
- Black Mass (2015) – Synopsis
- Whitey Bulger Isn’t too Happy With Johnny Depp in ‘Black Mass’
- ‘Whitey’ Bulger’s ex-girlfriend Catherine Greig indicted – CNN.com
- Whitey Bulger Not Happy With Johnny Depp’s New Movie, ‘Black Mass’
- Whitey Bulger, Notorious Mobster, Furious About ‘Black Mass’ Movie
- ‘Whitey’ Bulger disciplined at Florida prison for sexual activity – The Boston Globe
- Gangster James Whitey Bulger’s belongings to be auctioned | Fox News
- Whitey Bulger’s apartment in Santa Monica, Calif.
- Former FBI Agent Pleads Not Guilty to Perjury, Obstruction in Bulger Trial
- World Jai Alai, Mob Hits, And The Fbi: A Chronology – tribunedigital-thecourant
- How the ‘Black Mass’ authors watched their book come to life on screen
- TIMELINE: The case against James ‘Whitey’ Bulger | FOX25
- James “Whitey” Bulger: Timeline – CBS News
- WGBH News: Timeline: ‘Whitey’ Bulger’s Life In Boston
- James “Whitey” Bulger timeline | Timetoast timelines
- Whitey Bulger Timeline: A Life Of Crime « CBS Boston
- James Whitey Bulger timeline | World History Project
- Key events in the life of James ‘Whitey’ Bulger | Fox News
- Whitey Bulger – Wikipedia
- Whitey Bulger – Organized Crime – Biography.com
- Whitey Bulger’s Enforcer Slams ‘Black Mass’: ‘The Movie Is Pure Fiction’ – The Daily Beast
- Whitey learned to talk early on – Metro Desk – Boston.com
- Whitey Bulger was his dad – The Boston Globe
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Note: This transcript is automatically generated. There will be mistakes, so please don’t use them for quotes. It is provided for reference use to find things better in the audio.
Our story begins in the historic Dorchester neighborhood. That’s an area spanning about six miles that used to be its own town when it was founded in 1630, but as Boston started to grow it absorbed many of the surrounding towns. One of those was Dorchester, which officially became a part of Boston in 1870.
Dorchester is located on the south side of Boston, right along the Dorchester Bay, which is the smallest of the three bays that make up the southern part of the Boston Harbor.
It was here in Dorchester that James Bulger was born on September 3rd, 1929 as one of six children.
Growing up, James had shock of platinum-blond hair that earned him the nickname “Whitey.” But he hated this nickname. So any of his friends or simply acquaintances who didn’t want to get on his bad side called him Jimmy.
After his father, James Sr., lost his arm in an industrial accident—he was a union laborer and longshoreman—the Bulger family dipped to poverty. We don’t know if that’s the reason, but poverty and crime tend to go hand-in-hand. So it might make sense that James Jr., who had joined a street gang in Boston was arrested for stealing in 1943, at only 14 years of age.
That may have been his first time being arrested, but it was hardly his last. After this first arrest, he racked up other charges for assault, forgery and even armed robbery. Finally, he was sentenced to a juvenile detention center.
And that’s where Jimmy spent most of World War II as a teenager. In April of 1948, he joined the U.S. Air Force where yet again he got into trouble. He ended up serving time in a military jail for going AWOL as well as assault charges.
Jimmy was in the Air Force for about four years, and despite all of his charges he racked up while he was there, he received an honorable discharge in 1952.
Amazingly, he wasted no time in returning to a life of crime. For four years, Jimmy started to earn a name for himself. Or, more accurately, Whitey Bulger started to earn a name for himself—remember, only his friends called him Jimmy. And he was quickly making plenty of enemies.
In 1956, Whitey Bulger was arrested yet again. This time it was for probably one of Whitey’s biggest crimes yet, a full-fledged bank robbery. Interestingly, this was also the first time Whitey gave information to the FBI.
His girlfriend was a woman named Jacqui McAuliffe, and although Jacqui wasn’t one of the three who robbed the Industrial National Bank in Pawtucket, Rhode Island in May of 1955, she was close enough to Whitey to have been involved. That was the first in a string of bank robberies that Whitey pulled off with a few accomplices.
That came to an end in 1956 when Whitey caught wind that one of his accomplices, a man named Carl Smith, was going to turn him into the FBI.
So instead, Whitey did it first. He told the FBI who helped him with the robberies and also convinced Jacqui to do the same. In exchange, the FBI cut a deal to not press charges against Jacqui.
And they didn’t.
Whitey Bulger was sentenced to 20 years in prison while Jacqui went free. His first term was at the Atlanta Penitentiary. It was here that, according to Whitey, he had been drafted into the MK-ULTRA program.
If you’re not familiar with what that is, that’s the CIA’s top secret mind-control program. According to Whitey, he and 18 other inmates volunteered to take a range of drugs, including LSD, in exchange for a reduced sentence.
Later, Whitey would say the drugs drove him to insanity. We don’t know if this was the reason why, but in 1959, the guards caught onto a plot to escape. So they transferred Whitey to Alcatraz just outside of San Francisco.
He officially arrived at Alcatraz on November 2nd, 1959 and stayed there until November of 1962 when he was transferred to Leavenworth Federal Penitentiary in Kansas. His final transfer was a year later in 1963 when he was sent to the Lewisburg Federal Penitentiary in Pennsylvania.
In 1965, Whitey was granted parole on his third petition. He had only served nine years—less than half of his sentence.
Heading back to Boston, Whitey again wasted no time going back to a life of crime. As soon as he returned to Dorchester, he joined as the top lieutenant of Howie Winter’s gang out of Somerville, Massachusetts. That’s on the north side of Boston, 10 miles north of Dorchester.
It was a gang referred to by the local newspapers as the Winter Hill Gang. Although it wasn’t named after the gang’s Boss, Howie Winter. Although, technically, Howie was the second Boss of the gang. He took over in 1965 when the original Boss, James “Buddy” McLean, was killed in an area of Somerville called Winter Hill.
That’s why the local newspapers called them the Winter Hill Gang.
Around this time, another member of the gang named Stephen Flemmi informed on some members of the New England Mafia to an FBI agent named Paul Rico.
Paul Rico is the same FBI agent who arrested Whitey Bulger in 1956 after the bank robbery.
Four years later, Paul Rico returned the favor to Stephen Flemmi, and tipped him off of an indictment that was coming for Stephen’s involvement in a murder of Joe Barboza’s attorney, a man by the name of John Fitzgerald. Joe’s nickname was “The Animal”, and he was probably one of the most feared hitmen in the 1960s as he murdered at least 26 people for the Patriarca crime family. Of course, that number has never been confirmed.
To take out Joe’s attorney, John, Stephen used a car bomb with the help of a man named Frank Salemme. But of course don’t all mobsters have nicknames? Frank was “Cadillac.”
Both Frank and Stephen fled Boston with Frank heading to New York City while Stephen went to Montreal.
Meanwhile, in 1970, William Bulger, Whitey’s younger brother, was elected to the state Senate.
Two years after this, an FBI agent named John Connolly recognized Frank “Cadillac” Salemme in New York City. He was arrested, and it was because of this arrest that John earned a transfer to Boston—his hometown.
Two years later still, in 1974, Stephen Flemmi returned to Boston when some of the witnesses mysteriously recanted their accounts. No witnesses, no indictment. Upon returning to Boston, Stephen joined up with Howie Winter’s gang and meets Whitey.
And after that rather in-depth timeline, we’re finally to 1975 when the movie Black Mass begins.
Well, technically it starts after that as in the first scene we see Kevin Weeks, who’s played by Jesse Plemons in the film, talking to an FBI agent named Eric Olsen, who’s played by Lonnie Farmer. We get the sense that Kevin is informing on Whitey.
That’s true, and based on what we know of the timeline it was in 1999 when Kevin Weeks ended up cooperating with the law. He had been arrested on his own charges, and helped give information on Whitey in exchange for a reducing of his own charges.
And with that, in the movie, we’re whisked back to 1975. We first meet Whitey Bulger, who’s played by Johnny Depp, as he’s watching John Martorano for licking his fingers and then pulling nuts out of a bowl. In the movie John Martorano is played by W. Earl Brown.
This particular scene is one that the real Kevin Weeks later called out as being untrue. Not just untrue, but completely and utterly untrue.
According to Kevin, who saw Black Mass on opening night, if that incident with the bowl of nuts really happened, it’d be a really short movie. He explained this in an interview with the online publication Daily Beast, and explained John Martorano never went into the Triple O’s bar. So obviously that couldn’t have happened.
And even if it did, John—or Johnny as Kevin calls him—was even more vicious than Whitey. You see, Johnny’s nickname was “The Basin Street Butcher.” If Whitey would’ve made fun of him, Johnny would’ve shot him on the spot. Wouldn’t have been much of a movie with the main character dying in the first few minutes.
Oh, and another detail Kevin made sure to point out was the way Whitey talked down to John. According to Kevin, Whitey never swore at them. He made a special point to say that for the entire time Kevin had worked with Whitey, which was from 1976 to 1999, Whitey never swore in the way that’s depicted in the film.
Back in the movie, the next big scene is when Kevin earns his way into the Winter Hill Gang. He and Whitey drive a man into the middle of nowhere and start beating him senseless.
In the movie, as Kevin beats him up, Whitey says their victim’s name—it’s Joey Angiulo.
The movie says this in such a way that it seems to expect you know who this is, but if you don’t, let’s take a moment to find out.
The Angiulo Brothers, as they’re called, were four brothers that were the largest Italian-American crime family in the Boston area. The guy depicted in the movie, Joey, wasn’t one of the original brothers, but rather was the nephew of Gennaro—or “Jerry” as he was called.
Again, this is a scene that the real Kevin Weeks took issue with. He said this never happened. But he went even further, explaining that if it had happened that would’ve sparked a war between the Angiulo crime family and the Winter Hill Gang.
That in and of itself, according to Kevin, would’ve caused the streets of Boston to run red with blood.
If that didn’t happen, where did the scene come from? Well, Kevin explained that, too. He said the guy he beat up was a man named Paul Giaimo who had slapped Whitey’s niece. So Whitey and Kevin drove him out into the M Street Park, which is just along the coast of Dorchester Bay in South Boston.
But they didn’t leave him lying there like the movie shows. Instead, after bloodying him up, they dropped his body off by his friends place so they could see.
Much later, according to Kevin, they realized they beat up the wrong person. It wasn’t Paul Giaimo who slapped Whitey’s niece.
After this in the movie, we see John Connolly, who’s played by Joel Edgerton, come home. That is, he’s been reassigned to Boston.
This is a little off from the actual timeline. As we learned earlier, John Connolly earned his transfer back to Boston in 1972, and since the movie shows the flashback starting at 1975, the timeline is a little off.
And that’s not the only time the movie’s timeline is off; but we’ll get to that later.
However, the movie shows John Connolly making a deal with Whitey Bulger. An alliance between John and Whitey. John would provide Whitey with information from the FBI’s side, and Whitey would give John the information he needed to take down the Angiulos family.
While we don’t know the details of how the cooperation took place, what we do know is that John Connolly and Whitey Bulger did end up cooperating. This arrangement was mutually beneficial because it helped John grow his career in the FBI while at the same time it helped clear the streets from Whitey’s competitors in the Angiulos family.
But according to Whitey’s right-hand man, Kevin Weeks, that’s not exactly how it happened. Kevin explained that John was considered just as much a criminal as anyone else on the payroll.
Every time they made a big score, some money was set aside for paying all of their law enforcement contacts—John included.
One of the next scenes in the film gives a peek into Whitey’s personal life when we see his girlfriend Lindsey Cyr and their son Douglas. In the movie, Lindsey is portrayed by Dakota Johnson while Douglas is played by Luke Ryan.
Over the dinner table, Douglas explains to his father that he got in trouble at school for hitting someone. To which Whitey calmly explains that it’s not about whether or not you should hit someone, but it’s about making sure no one is looking when you do it. If no one is looking, it didn’t happen.
This portrayal in the film is yet another thing Kevin Weeks says is completely fictional. In his interview with Daily Beast after seeing the movie, Kevin explained that’s not how Whitey was with kids.
In truth, according to Kevin, Whitey’s character around kids, his own included, was more similar to what you’d think a stereotypical mobster would be with kids. That is, very cordial and friendly. Kevin explained that Whitey was the godfather to one of his sons, and he remembered nothing like the push toward violence portrayed in the film. Instead, when Whitey talked with kids, it was mostly chatting about how things are going, about baseball—you know, normal conversations.
According to Kevin, business never made its way back to the house.
One of the turning points in the movie is when Whitey’s son, Douglas, is in the hospital with Reye’s syndrome.
This is partially true. What’s true is that Douglas Cyr, the son of Whitey Bulger and Lindsey Cyr, did get sick seemingly all of a sudden. Born in 1967, he fell sick with a severe reaction to aspirin and died of Reye’s Syndrome in 1973 at only six years of age.
According to Lindsey, after Douglas passed, Whitey became even colder and more distant. He changed.
But if you’ll notice something with the dates there, you’ll notice the movie has changed the timeline rather significantly. Douglas passed away in 1973, but at the beginning of the movie it flashes back to 1975.
While the movie makes it seem like Douglas’s death was a turning point for Whitey in the middle of the film, that’s simply not true. That is to say, it certainly might have been a turning point for Whitey—as it would be for any father to lose their son at only six years of age—but this happened before the timeline of the movie. So the filmmakers fudged the timeline a bit here to make Douglas’s death seem like the reasoning for Whitey’s increasingly violent behavior.
Back in the movie, the timeline skips forward to 1981.
Before we jump forward with the movie, let’s cover a few of the important things that happened in those six years.
In 1977, John Morris, who’s portrayed by David Habour in the film, took on the task of overseeing many of the agents in Boston. One of those was John Connolly.
The next year, in 1978, Whitey’s brother William, who’s played by Benedict Cumberbatch, became the president of the state Senate. Not to get ahead of ourselves here, but William Bulger would serve as the president of the state Senate longer than anyone else in history.
Probably the most important event in this span that’s skipped over by the movie happened in 1979. It’s one of those things that we know just enough about to get a picture of what happened, but we don’t know enough of the details to know if the picture we’re getting is correct or not.
At this point, Whitey Bulger was still the lieutenant in the Winter Hill Gang. The same position he’d been in since he returned to Boston fourteen years earlier. Regardless of whether or not John Connolly at the FBI was crooked at this time, we know Whitey was feeding information to him at the FBI.
Some of that came when Whitey passed on information he and Stevie Flemmi had gathered on his own Boss, Howie Winter. We don’t know exactly what the information was, but it was because of this information that the FBI was able to grab quite a few members of the Winter Hill Gang, including Howie Winter.
So in 1979, Howie Winter was one of the 21 gang members who were arrested on charges of money laundering, income tax evasion and horse race fixing. That’s the official line, at least. I’m sure there was plenty else that the FBI was trying to get them on—those are just the charges they could prove.
Of the 21 who were charged, thanks to John Connolly and John Morris, both Whitey Bulger and Stevie Flemmi were the only two left out of the indictment. John and John managed to do this because both Whitey and Stevie were informants for the FBI.
With Howie Winter locked away, the title of Boss was vacant for the Winter Hill Gang. And who should step into the new role than one of Howie Winter’s old, “trusted” lieutenants?
So in 1979, James “Whitey” Bulger took over as only the third Boss of the Winter Hill Gang since its inception in 1950.
Back in the movie now, we’re in the year 1981 and Whitey gives John Connolly some information on a meeting with the Angiulos. This is something Joel Edgerton’s version of John Connolly delightfully gives Kevin Bacon’s version of FBI agent Charles McGuire.
And this is true. Well, like most of the details we don’t really know exactly if it happened in this way, but we do know that both Whitey Bulger and Stevie Flemmi helped the FBI with planting a bug in the Boston Mafia’s headquarters. That’s the Mafia run by the Angiulo brothers, or more specifically at that time Gennaro “Jerry” Angiulo.
Another moment in the film comes with a cold blooded murder when W. Earl Brown’s version of John Martorano walks up to Roger Wheeler, who’s played by David De Beck in the film, and guns him down in broad daylight.
This, too, is true. It happened in May of 1981 and Roger Wheeler was the owner of World Jai Alai.
Now in the movie they mention jai alai quite a bit, but there’s only a very brief mention of exactly what that is. I had to look it up afterward to understand how this fit into the story.
Just to clarify, jai alai is a game sort of like racquetball. It’s more common in Latin American countries or in the Philippines, but globally its popularity has diminished quite a bit in the past few decades.
All of this fits into the story not because of the sport itself, but because Roger Wheeler owned a company called World Jai Alai. As you can probably guess from the name, World Jai Alai was sort of like a fitness club—but it was primarily focused on the sport of jai alai.
Anyway, to understand how this fits into the story we have to go back in time real quickly. In 1974, World Jai Alai hired a man by the name of John Callahan as its president. In the movie, John Callahan is played by Bill Camp. One of John’s first acts as president of the company was to hire a man named Paul Rico to be a vice president and chief of security.
Remember that name? Paul was the FBI agent who had arrested Whitey Bulger some years ago. At this point, though, Paul had retired from the FBI.
Two years later, John Callahan left World Jai Alai because it became public that he had mob connections. No doubt the company knew about this before, but at this point they hurt the company’s chance at a licensing deal, so they essentially forced him to resign.
The next year, a businessman from Tulsa, Oklahoma, decided to buy World Jai Alai. That businessman was Roger Wheeler.
Oh, and as a quick side note, two of the people who placed competing bids to buy the company mysteriously backed out. Was there pressure by the mob allowing Roger to get the company?
That’s a detail we don’t know.
What we do know is World Jai Alai was a front the Winter Hill Gang used to skim money.
In the movie, the lead-up to this coldblooded murder of Roger Wheeler came by way of a meeting in Miami. It’s here that, according to the movie, Whitey, Stevie, Kevin Weeks and Johnny—that’s “The Basin Street Butcher”, John Martorano, all meet up to discuss the hit on Roger Wheeler.
The film shows these men talking to John Callahan, the former president of World Jai Alai. It’s John who hands Whitey a bag of money to pay for the hit. Whitey doesn’t take it, but instead hands it to Brian Halloran, who’s played by Peter Sarsgaard.
While we’ll likely never know the exact words used, according to Kevin Weeks the real discussion was nothing like what we see in the movie. Instead, Kevin explained, the real meeting took place in a hotel by La Guardia Airport in New York City.
And John Callahan wasn’t there. Instead, according to Kevin, it was Johnny Martorano, Stevie Flemmi and Whitey who met. The discussion wasn’t around killing just Roger Wheeler, but rather about taking out both John Callahan and Roger Wheeler.
Kevin Weeks, according to the man himself, wasn’t ever there. He insists he only found out about Roger Wheeler’s murder after John Callahan was murdered. So we can deduce he only knew about the meeting because it was discussed later by those who were there.
Or you could assume Kevin’s not telling the truth. But seeing as we have no one else’s word to take, we have nothing else to compare it to.
What we do know is, just like the movie shows, Roger Wheeler was gunned down in broad day light outside of a country club in Tulsa, Oklahoma. His death involved the Tulsa police, which received a tip from an informant two months after his shooting, in July, that the Winter Hill Gang was involved.
And again, although we don’t know the exact details surrounding it, John Callahan was murdered as well. Most believe this happened in July of 1982, a couple months after Roger Wheeler was murdered. But it wasn’t until August of 1982 that John Callahan’s decomposing body was found stuffed into the trunk of a Cadillac in the airport parking garage in Miami. He had been shot multiple times in the head, and there was a dime carefully placed on his chest.
The Miami detectives on the case came to the conclusion that John Callahan was murdered at the World Jai Alai’s fronton—that’s what you call a building where jai alai is played—and then taken to the airport.
Roger Wheeler and John Callahan were murdered so they wouldn’t talk to investigators about the money the Winter Hill Gang was skimming off of the World Jai Alai company.
In the movie, everything starts to come crashing down for Whitey Bulger when two FBI agents start looking closer at John Connolly. It’s been a little bit since we’ve talked about this John, but he’s the FBI agent who was on Whitey’s payroll.
The movie shows the two FBI agents behind the uncovering as being Kevin Bacon’s character, Charles McGuire, and Corey Stoll’s character, Fred Wyshak. In the movie, they get a break when John Morris—that’s David Harbour’s character—ended up spilling the beans on Whitey and John Connolly’s connection.
Before we dig into the truth here, I should point out that using the term “truth” is really shaky ground. The truth is we simply don’t know. Like many of the facts in this situation, we’re talking about either an investigation from the FBI or another government entity and organized crime.
So either the facts are hidden, covered up, or maybe they aren’t even facts at all. We just don’t know.
But let’s start with one thing we know for sure. Everyone at the FBI knew John Connolly was working with Whitey Bulger and Stevie Flemmi.
They assumed, though, that Whitey and Stevie were informants. The movie is correct in showing that the two FBI agents who started to dig into what was going on were Fred Wyshak, who’s played by Corey Stoll in the movie, and Charles McGuire, who we learned earlier is played by Kevin Bacon in the film.
As they dug deeper into things, Agents Wyshak and McGuire started to realize the connection between John Connolly, Whitey and Stevie were more than just a typical informant connection.
But where it gets cloudy is we don’t really know who else was involved. Or was there anyone else involved? Were Agents Wyshak and McGuire really good FBI agents who caught onto the fact that something was stinky with John Connolly and Whitey Bulger? Or were they part of a cover-up that threw former Agent Connolly and Whitey under the bus to save their own behinds?
You can get super into the conspiracy theory side of this, so I won’t dig into “what might have been” scenarios here. It’s worth pointing out, though, that in his interview with the Daily Beast about the film, the real Kevin Weeks mentioned an FBI agent who gave the Winter Hill Gang about 37 pounds of C-4 so they could pull off a hit against a Boston reporter.
He also mentioned how a man named Jeremiah O’Sullivan, who’s played by Lewis Wheeler in the movie, also gave information to John Connolly to give to Whitey. Jeremiah was another member of law enforcement, but he wasn’t FBI.
Jeremiah O’Sullivan was the head of the New England Organized Crime Strike Force that was credited with helping to bring down the Winter Hill Gang as well as “Jerry” Angiulo. Did they do the latter with help from Whitey?
Again, you can get super into a conspiracy theory mindset here, but no one can deny it’s really fascinating.
The final shot in the movie is one of an elderly Whitey Bulger. He’s walking into a parking garage when the FBI jump out and arrest him.
This is true.
Well, like many of the scenes in the movie, we don’t know if it went down exactly like what we see in the movie, but Whitey Bulger did get away with his crimes for a long time.
Realizing the end of his reign was near, Whitey Bulger got his final tipoff from John Connolly that indictments were sealed and delivered from the Department of Justice.
On December 23rd, 1994, Whitey simply disappeared along with his common-law wife, Theresa Stanley.
The movie doesn’t show any of this, and law enforcement certainly didn’t know it at the time, but after Whitey Bulger disappeared he went to Selden, New York. Selden is a small town on Long Island just to the east of New York City.
He only stayed there for a few days, heading to New Orleans just before New Year’s Day in 1995. Soon after, he almost returned to Boston, but on January 5th, 1995, Stephen Flemmi was arrested by the DEA.
Stephen’s brother, Michael, was a detective for the Boston police department and he mentioned the arrest to Kevin Weeks who, in turn, tipped off Whitey.
After Whitey went into hiding, Kevin Weeks took over as the Boss of the Winter Hill Gang.
They’d only been on the run for a few weeks when Whitey’s common-law wife, Theresa, decided she wanted to go back to be with her children. We don’t really know exactly how much time spanned between these events, but Whitey would admit later he took Theresa to Florida first. There, Whitey picked up some documents he had locked away in a safe deposit box for a new identity. Whitey Bulger was now Tom Baxter.
Then the couple left Florida and went back to Boston where Whitey said goodbye to Theresa. While she went back to live in her hometown so she could be close to her children, Whitey went back to his own hometown of Dorchester where he met up with Kevin Weeks. Kevin brought with him Catherine Greig, Whitey’s longtime girlfriend.
So, yeah, Whitey dropped off his common-law wife and picked up his girlfriend.
Together, Whitey and Catherine went on the run.
Four years after he disappeared, Whitey Bulger made his way to the FBI’s Ten Most Wanted Fugitives list. He stayed on that list for the next 12 years. In that time, the FBI fielded a lot of reports of Whitey around the world.
He was in London. Then he was in Uruguay. No, he’s in Sicily. Now he’s in Germany.
The tip that paid off came in on June 21st, 2011. The Boston Globe would later report the tip came from a former Miss Universe contestant from Iceland named Anna Bjorn who said she lived in the same neighborhood as Whitey.
The next day, on June 22nd, 2011, and at the age of 81 years old, James “Whitey” Bulger and his girlfriend, Catherine Greig, were arrested at their apartment in Santa Monica, California.
The movie shows Whitey’s arrest coming in a parking garage, but the official terminology used by the reports from the task force who captured him was that they orchestrated a ruse to get him to come out of the apartment. When he did, they arrested him without incident. Then, they went inside the apartment and arrested Catherine.
On June 12th, 2013, Whitey Bulger went on trial as he faced 32 counts of racketeering under RICO, or the Racketeer Influenced and Corrupt Organizations Act of 1970 that’s used to prosecute organized crime.
Included in the charges were conspiracy to commit extortion, committing extortion, shoplifting, narcotics distribution, conspiracy to commit money laundering, conspiracy to commit murder and 19 counts of murder.
The trial could be an episode in and of itself as it spanned two months and had a total of 72 people coming forward as witness.
It came to a close on August 12th when Whitey was convicted with 31 of those 32 counts. Included in that were the convictions of 11 murders.
Alphabetically, they were:
Arthur Barrett, John Callahan, Richard Castucci, Edward Connors, Michael Donahue, Brian Halloran, Deborah Hussey, Thomas King, Paul McGonagle, John McIntyre, and last, but certainly not least, Roger Wheeler.
Whitey Bulger was sentenced on November 14th, 2013. He received two life terms in prison, with an additional five years tacked on top. In addition, he was forced to pay $44.7 million in restitution.
Oh, and the law enforcement in both Florida and Oklahoma have indicted Whitey for the murders of John Callahan in Florida and Roger Wheeler in Oklahoma. If by some chance, he survives his multiple life sentences he would then be charged by those states.
That’s not likely, though, since when he was convicted, Whitey Bulger was 84 years old.
On June 25th, 2016, many of the possessions found in the Santa Monica apartment were auctioned off in an attempt to pay the restitution. It only raised about $109,000.
As of this recording, Whitey Bulger is still alive at the age of 87 and is currently serving his life sentence in the United States Penitentiary Coleman II in Sumterville, Florida.
As you can probably guess, there’s so much more to this story. We didn’t even get to talk about what happened to William Bulger’s political career, what happened to players like Kevin Weeks and why he’s now been willing to open up about a lot of what’s happened, and not even to mention the countless conspiracies and theories around it all.
One thing’s for sure, Whitey Bulger was an incredibly vicious man who was both directly and indirectly responsible for the murder of many people. Exactly how many, we may not ever know.
And while Kevin Weeks certainly isn’t innocent by any means, his testimony helped bring Whitey to justice and find many of the bodies of his victims.
According to Kevin? It’s the FBI who enabled Whitey Bulger and Stevie Flemmi to do the things they did.