Episode 82 | The Brutal Life And Death of American Mobster Whitey Bulger

It’s 6 am, October 30th, 2018. 89-year old former mobster-turned-informant,   Whitey Bulger is sitting in his wheelchair inside his brand-new home at USP, Hazelton Prison. He had only arrived hours earlier. The cell door had just been unlocked for breakfast and three fellow prisoners are headed his way and Whitey won’t live tell his side of the story. His long life of violence as a Mob boss and enforcer of the notorious 'Winter Hill Gang'  comes full-circle. Is it karma? Why was he transferred to a prison where he was certain to be a target?

In this podcast we're going to take a journey through a man’s life that goes way beyond just being a mobster. A man who was a prisoner in Alcatraz. A man who was experimented on as part of the CIA’s MK-Ultra program. A man who was once considered to be the 2nd most wanted individual on the FBI’s Ten Most Wanted Fugitives list, behind only the OG himself Osama Bin Laden. ★Enjoy!

★PLEASE RATE THE PODCAST:
I’d like to as a quick favor - please rate/ review the Homicide Inc podcast if you haven’t already. Click the stars (all 5 if you fancy) and leave a review if you would. Thanks!
https://podcasts.apple.com/jp/podcast/homicide-inc-classic/id1548239093?l=en

★NEED MORE HOMICIDE INC.? Check out our PATREON campaign for exclusive Homicide Inc. podcasts available only to Patrons!
https://www.patreon.com/petervongomm

★THE HOMICIDE INC. WEBSITE is here! All podcasts are available on the website.
https://www.homicide-inc.com

★DISCORD CHAT! Want to chat about the Homicide Inc. podcasts and crime in general? Join us on our Discord server here.  https://discord.gg/peBqDfT6

★ WHO AM I ?
My name is Peter von Gomm and I'm a professional Voice actor and Narrator and in this podcast I'll be bringing you high quality True Crime that passes the test of time. You've come to the right place for a great story!

★PODCAST SUPPORT
If you like these Podcasts and would like to help support their production, please consider buying me a cup of coffee! This will help keep me wired for writing and recording these weekly podcasts, and contribute towards web and podcast hosting. Thanks very much indeed! :0)  buymeacoffee.com/petervongomm

★STORY SUBMISSION
If you have an INTRIGUING TRUE STORY to share and would like me to consider reading it in a podcast, please submit it to petervongomm.reads@gmail.com
*It must be well-written please. ;0)

★Homicide Inc. theme song by Christopher J. Orton
https://www.fiverr.com/meandamic
*Guitars played by Joao Corceiro
https://www.fiverr.com/joaocorceiro

SOURCES for this episode:
https://drive.google.com/file/d/1wqNfUrigbLaC2jl4L1CyspUG_xKG_vpp/view?usp=sharing

#murder #truecrime #whiteybulger #mafia #mob #podcast #truestory #homicide #homicideinc #crime #investigative #killer #horror #truecrimepodcast #prison #truecrimecommunity 

https://www.homicide-inc.com

Transcript

The Brutal Life And Death of American Mobster Whitey Bulger

Prologue

It’s 6 am, October 30th, 2018. Whitey Bulger, 89-year old Mobster-turned-informant, is sitting in his wheelchair in his prison cell, the door had just been unlocked for breakfast. Three men are headed his way and he won’t live tell his side of the story. 

- Fotis (Freddy) Geas, a known Mafia enforcer from Massachusetts serving a life sentence for a pair of gang-related murders.

- Paul DeCologero, a member of a Massachusetts gang which murdered a teenage girl who they thought knew too much, with four years left on a 25-year sentence for his involvement in that.

- And Sean McKinnon, a low-level crook tagging along. 

How did poor elderly piss-pants Whitey get to this point? 

In order to answer that, we’ll have to take a journey through a man’s life that goes way beyond just being a mobster. A man who was a prisoner in Alcatraz. A man who was experimented on as part of the CIA’s MK-Ultra program. A man who was once considered to be the 2nd most wanted individual on the FBI’s Ten Most Wanted Fugitives list, behind only the OG himself Osama Bin Laden.

But we’ve gotta go back just a little bit first.

Act I

James Joseph Bulger – no Whitey yet – was born on September 3rd, 1929, in Boston to working-class Irish immigrants. Bulger’s father was a union laborer, occasionally working as a longshoreman. At some point, he lost his arm in an industrial accident. The family was reduced to poverty.

In May 1938, the Mary Ellen McCormack Housing Project opened in South Boston. The impoverished Bulger family soon moved there, and that’s where Whitey was born. 

From early on, the brothers’ paths started to diverge – William Bulger excelled at school, while James was already slowly getting drawn into street life. His first arrest came at age 13. Juvenile delinquency. 

It started with shoplifting, stealing from the back of trucks making deliveries. Soon enough, it apparently became a favorite activity of his to lure homosexuals, who would then be robbed and beaten. 

It was around that time that he earned the name ‘Whitey’ (in reference to his white-blond hair), a nickname that he actually hated, preferring to go by Jim, though apparently he was also willing to settle for ‘Boots’ (because it referenced Bulger’s penchant for pulling a switchblade out of his cowboy boots). 

But, he’s not known as Boots Bulger. 

It was also around this time that he met an eight-year old boy, named John Connolly. Already nineteen himself, he would buy him an ice cream, and later save him as he was being beaten up by an older boy. ‘Go fight someone your own size,’ he said, as young Connolly stared in awe. A chance meeting that would alter the course of both of their lives. 

In 1956 he was convicted for a string of bank robberies committed in three states, and sentenced to 20 years in prison. 

While imprisoned, Bulger volunteered to take part in experiments in return for a reduced sentence. There he was unwittingly used as a human subject in the CIA sponsored MK-ULTRA program, and was injected with the hallucinatory drug LSD, among others.

Project MKUltra (or MK-Ultra) was an illegal human experimentation program designed and undertaken by the U.S. CIA  with the intention to develop procedures and identify drugs that could be used in interrogations to weaken individuals and force confessions through brainwashing and psychological torture. It started in 1953,  and ran for 20 years until it was halted in 1973. MKUltra used numerous methods to manipulate its subjects' mental states and brain functions, such as the covert administration of high doses of psychoactive drugs (especially LSD) and other chemicals, electroshocks, hypnosis, sensory deprivation, isolation, and verbal and sexual abuse, in addition to other forms of torture. Phew!

Bulger was already a dangerous criminal before his Atlanta prison sentence, but some say that the psychological effect of the MK-Ultra tests made his temperament even worse, shaping him and who he would become to an extent. I think we can imagine this could be the case! That is one brutal program! And he volunteered!?

Bulger described his experience in the MK-Ultra program as ‘nightmarish’ and taking him to the ‘depths of insanity.’ In fact, he apparently never revealed the full extent of his experience because he was concerned that he would be committed to a mental institution for the rest of his life. 

In 1959, Bulger was briefly transferred to maximum security at Alcatraz Federal Penitentiary, and after a few other stops, he was granted parole in 1965. This would be the last time he would do prison time for the next 46 years. 

When Bulger returned to Boston, he would find that his stint at Alcatraz had boosted his reputation significantly. In the early 1970s, Bulger would become an enforcer for the Winter Hill Gang, a predominantly Irish American crime syndicate. 

In 1975, Bulger agreed to work with the FBI as a so-called “Top Echelon Informant.”  His handler would turn out to be none other than John Connolly, his childhood friend . And their relationship would soon turn corrupt, later described as a ‘devil’s deal’, and giving rise to the worst informant scandal in FBI history. Bulger would supply the FBI with information on the Italian Mafia if the Feds would guarantee him their protection.

If one were to ask Bulger, however, he was never an informant. His entire life he maintained that he ‘never cracked. Never, never.’ 

He couldn’t deny that the meetings with Connolly had taken place, but what he would do is claim that he was the one handling Connolly, that he was using the FBI and their resources to his advantage, not the other way around: ‘I was the guy who did the directing. They didn’t direct me.’ 

In 1979, both the boss and deputy of the Winter Hill Gang were arrested for fixing horse races, and Bulger took over the gang’s leadership (only escaping conviction himself due to the special protection provided by Connolly).

Throughout his reign, Bulger would take full advantage of this relationship. Connolly frequently alerted Bulger to other authorities’ investigations into the Winter Hill Gang’s operations, and would cast a blind eye even to murders committed, becoming an invaluable asset. 

Act II

By 1994, however, the hammer was finally about to come down. A case had been built against Bulger through a joint task force of the DEA, the Boston Police, and the Massachusetts State Police (the FBI, by this time considered compromised, was not informed), and arrests were imminent.

Bulger reportedly called John Morris, Connolly’s supervisor, and told him ‘if I’m going to jail, you’re going to jail. I’m taking you with me.’ 

Shortly after, Morris suffered a heart attack. So terrifying was Whitey Bulger, so unnatural his reach, that he almost killed an FBI agent via phone call. 

In December 1994, Connolly did one last favor for his childhood friend, and warned him of the coming indictment. 

Bulger fled Boston, while all of his high-level associates in the gang were arrested. And that’s when a 16-year manhunt for an increasingly legendary Whitey Bulger began. 

The first confirmed sighting of Bulger was in London in 2002, by a businessman who only realized who it had been later on while watching the movie Hannibal, during a scene in which a detective hunting for Hannibal Lecter scans the FBI's most wanted list on the Internet, and flips past Bulger's image. Many unconfirmed sightings were also reported. Two people on video footage shot in Sicily in April 2007, thought to be Bulger and girlfriend Catherine Greig, were later identified as a tourist couple from Germany. At one point, FBI agents were sent to Uruguay to investigate a lead. 

In 2010, based on Bulger being a known book lover, the FBI scoured bookstores on Vancouver Island, questioning employees and distributing wanted posters. They also sent agents to stake out 60th anniversary celebrations of the Battle of Normandy, due to Bulger reportedly being an enthusiastic fan of military history. 

Digital age progression was also utilized, in order to generate an image of what Bulger might have looked like in 2004. 

Meanwhile all this time, Bulger was living with Catherine Greig as Charlie and Carol Gasko, in a seaside apartment in Santa Monica, California. Right under their noses. 

And beyond the fake identities, Bulger didn’t really even make too much of an effort to stay hidden. There had been multiple sightings of him at the Santa Monica Pier, where he apparently enjoyed hanging out. One man says he recognized Bulger in 2008, and contacted the television show America’s Most Wanted. Another witness says that he was on vacation with his family during spring of that same year when he saw Bulger, shirtless and reading a book. He also claimed to have called America’s Most Wanted, which had just broadcast a show on the notorious crime boss.

But that’s not anywhere near the most galling example, as it was during this time that Bulger would go back to Alcatraz – not as a prisoner this time, though. 

Just weeks after he fled Boston, Bulger visited Alcatraz with his then-girlfriend Teresa Stanley – and there’s even a photo to show for it. Bulger and Stanley posing outside ‘The Rock’ for a souvenir snap in mock prison uniforms, both stenciled ‘Property of Alcatraz’. And as if it couldn’t get worse, and more humiliating for the FBI, this was just part of an album of holiday snaps – all the time while on the run – showing the pair visiting Britain's Tower of London, dining in Paris and posing with the Stanley Cup.

They were generally polite, according to one neighbor, who also said that ‘they were kind of secretive. Even on the phone – you couldn’t call them.’ Another neighbor also described them as a polite, and quiet, couple, who sometimes helped carry her groceries.

In letters written after his capture, Bulger described that time as ‘a 16-year honeymoon’. 

So how was he actually, finally caught? After all the millions spent, the nearly two-decade long manhunt for him across the globe, all the technology and resources utilized? 

He was caught by a former Miss Iceland. 

Anna Bjornsdottir had lived next door to Bulger and Greig, or as she knew them, Charlie and Carol Gasko. She recognized her former neighbors in a 30-second FBI television ad aimed at women watching daytime television, which showed photographs of Greig and Bulger from the 1990s. So she picked up the phone, and turned in the 2nd most wanted man in the world. She collected a $2 million tipster’s fee for that phone call. 

According to a special agent in the Boston FBI office, the fact that the ad featured Greig as well, instead of just focusing on Bulger, was very much part of a targeted effort of them ‘trying to reach a different audience to produce new leads in the case. ... We believed that locating Greig would lead us to Bulger. And that's exactly what happened.’ 

Though there’s different accounts of the actual arrest, one claims that when the officers burst in, Bulger just rolled his eyes and said ‘I ain’t getting down on my fucking knees.’ 

On June 12th, 2013, Bulger went on trial on 32 counts of racketeering and firearms possession, including allegations that Bulger was complicit in 19 murders. 

On August 12th, the jury convicted Bulger of 31 out of 32 counts in the indictment, and found him culpable in 11 killings. 

On November 14th, Bulger was sentenced to tw   o terms of life imprisonment, plus five years.

Act III

The USP Coleman II penitentiary in central Florida has long been known as a safe haven for marked men in the federal prison system, aka prisoners guilty of any of a particular assortment of crimes and activities that are considered anathema even by other criminals, so much so that anyone that enters prison being guilty of one of these crimes or activities has a target on their back – such as government informants. A GED teacher at Coleman II was quoted saying that they ‘had a lot of snitches there, but they’re safe. Like that old saying, they’re among thieves.’

So naturally, that’s where Bulger was put and kept.

Until October 2018. 

All of a sudden, Bulger started getting transferred left right and center, going through multiple facilities in that month. On the 29th, he was transferred from the Federal Transfer Center in Oklahoma City to United States Penitentiary Hazelton in West Virginia, long known as one of the most violent destinations for prisoners. 

Nothing more needs to be said other than the fact that it was nicknamed ‘Misery Mountain’. 

Even in Coleman the warden was very clear about not taking any chances. He said he kept Bulger away from the general population for six months and talked to the most influential inmates to make sure they wouldn’t make a move on him. ‘He’s an old guy, but gangsters don’t forget’, he said. And here he was just dropped right into general population.

He lasted six minutes. 

It’s 6:06 am, October 30th, 2018. Freddy Geas (Ji-us), Paul DeCologero, and Sean McKinnon have reached Bulger’s prison cell. Geas and DeCologero enter. McKinnon does enter the cell, he’s on lookout, seated at a table where he can see both the unit’s officers station and into Bulger’s cell.

They were in there for about seven minutes. Bulger was savagely beaten to death with a sock-wrapped padlock, and the two assailants were also armed with a shiv. His eyes were nearly gouged out, and his tongue almost cut off. 

Afterwards, Bulger was described by a law enforcement official as ‘unrecognizable’. 

Literally not one person was surprised by this development. There was no reason for anyone to think that what happened to Bulger wasn’t going to happen. So that obviously begs the question:

Why? 

Why was Bulger transferred out of a facility famously known for its safety when it comes to marked prisoners, in order to be transferred into a facility famously known for its homicides, Bulger’s being the third in a 40-day span, and – according to correctional officers that had warned Congress just days before the most recent killing – dangerously understaffed?

At first glance, two possible explanations jump out: incompetence, or design.

Let’s start with the official reason given for his transfer. The explanation provided was medical in nature – Bulger’s health had apparently improved to such a point as to allow for his relocation, according to prison files obtained by NBC News. Prison officials specified on his transfer paperwork that he completed treatment at a medical facility, and was in good enough health to return to the general population.

But there are three main issues with that: 

First of all, there are other prison records that contradict the statement of him completing treatment, stating that he wasn’t at a medical facility before heading off to Hazelton, but locked up in solitary confinement. 

Secondly, as far as his alleged health improvements are concerned, that too is contradicted. According to jailhouse letters from Bulger to a California woman he corresponded with, he expressed his will to live despite deteriorating health, including eight heart attacks. And before his transfer, while still at Coleman, he was stricken with severe chest pains when a prison nurse conducted a series of tests and determined he needed to see an outside heart doctor.

And finally, above all of that, this explanation completely fails to take into account the most significant factor of them all, the fact that his return to the general population should have been first and foremost predicated on whether or not he was gonna get beaten to death in his first few minutes in general population, regardless of his health. As a factor, his health really only becomes relevant if the threat to his life, as a well-known rat, has first been negated.

Could it have been as banal and bureaucratic as just incompetence? 

Cameron Lindsay, a retired warden at three federal facilities called the case ‘a shocking failure on multiple levels.’ He stated that ‘there's absolutely no way Bulger should have been sent to Hazelton, and he sure as heck should never have been released to the compound at Hazelton. It's difficult to imagine how and why so many people dropped the ball on this thing.’

A recognition of failure, rather than a success of some intentional scheme – but already with a hint of confusion, and just genuine doubt at something of this magnitude having been caused by incompetence alone. 

The next person’s statement is far less confused:

Vito Maraviglia, a retired federal prison special investigative agent, who spent 27 years monitoring high-risk inmates and evaluating security threats in arriving prisoners, said that ‘unfortunately, it looks like they gave him the death sentence’. He added that ‘for people to say “I didn't know he'd get hurt there”, it's an outright lie. Either they were extremely negligent or just a complete idiot, and there had to be 10 idiots because a lot of people signed off on that.’

The Federal Bureau of Prisons, presented with a detailed list of questions, has declined comment. In a statement released, they simply said that ‘for safety and security reasons, we do not discuss specific conditions of confinement or whether an inmate has had a disciplinary history. We cannot comment further due to an ongoing investigation.’

Moving inmates between prisons is a common practice in the federal system. The transfers are done for multiple reasons, and are signed off on by a centralized unit in Texas and the two regional offices involved in the move.

Moving an inmate like Whitey Bulger, however, would very much not be business as usual. According to current and former prison staffers, the transfer process would have been started by the Coleman II warden. The request, after passing through layers of federal prison bureaucracy and ultimately getting the approval from the regional offices, would have generated paperwork that would eventually cross the desk of the Hazelton warden.

Bulger's dark past was not covered up on his intake screening form. It described him as a ‘Boston mobster involved in numerous murders and acts of violence. High Profile Case.’ His severity level was marked off as ‘greatest.’

Lindsay would go on to say that ‘the Hazelton warden and his staff were ultimately responsible, unless, of course, ordered by a higher authority, for deciding whether or not Bulger would be released to their general populat ion.’

So how about the explanation that it was all designed, purposefully orchestrated so that Bulger would be murdered?

The first thing to know is that, according to McKinnon, ‘everybody knew he was coming.’ McKinnon made sure to emphasize the commonness of this information, stressing that he heard it from just ‘another inmate – not even one of the guys from Massachusetts. It wasn’t like I got this secret news. I was just a little fish in the sea.’ 

In a phone call made from McKinnon to his mother just five hours before Bulger’s arrival at Hazelton, recorded by prison officials, he told his mother about it, saying ‘you should know the name… White Bulger’, to which she replied with ‘Oh Jesus… stay away from him please’, to which McKinnon replied with ‘Ah, I can’t’ (which may have been due to the fact that his cellmate was Geas – not helping him wasn’t an option).

Officials have yet to explain how the inmates knew of Bulger’s arrival.

At 5 am on the day of Bulger’s murder, Geas and McKinnon were seen on surveillance meeting with DeCologero in their cell. 

According to an Assistant US Attorney, Geas and DeCologero readily admitted to another inmate that they were the killers. DeCologero apparently told him that Bulger was a snitch, and that as soon as they saw him come into the unit, they planned to kill him.

According to an anonymous law enforcement source that spoke to Masslive.com, admission and proof of guilt is not an issue at all – quite the opposite, as the killing of a figure as derided as Bulger is a badge of honor, and rewarded in criminal circles. When referring to Geas, the source said ‘he’s a rich man now. He’ll run any prison he’s in.’

Undeniable foreknowledge, undeniable planning, undeniable motive. 

But even if we were to accept that this must’ve been done by design, that only spawns the next question – whose design?

That criminal elements were involved is not in question, the question is whether the intention to eliminate Bulger stemmed from even higher up. Were the criminal elements just tools to carry out (knowingly or not) someone else’s wish? The hands to do someone else’s dirty work, so theirs would remain clean?

On the two year anniversary of his murder, Bulger’s family filed a lawsuit against the U.S. Department of Justice, U.S. Bureau of Prisons and U.S. Marshals Service that alleges there was a conspiracy by the government to intentionally harm him, seeing $200 million in damages.

The family’s attorneys Hank Brennan and David Shoen left no room for interpretation in a letter to the Department of Justice. They wrote, ‘to be clear, we do not believe that the transfer to FCI Hazelton and placement in the general population was simply dangerous, negligent, reckless, and irresponsible. We believe it was also intentional and part of a conspiracy among BOP, DOJ employees, and others to intentionally cause Mr. Bulger's serious injuries and death.’

The family also put out a statement, saying that they ‘believe that James Bulger was deliberately placed in harm's way. There is simply no other explanation for the transfer of someone in his condition and inmate status to be placed in the general population of one of the country's most violent federal penitentiaries.’

The suit was dismissed in January of 2022, but not due to some judgement that it lacked in validity or credibility, but because, as per a US District Judge, ‘federal courts were barred by Congress from weighing in on prison housing decisions that resulted in injuries or death’. So the claim itself was never actually examined, it was thrown out before it could be examined.

Brennan has said that he believes the Justice Department deliberately waited to file the charges until after the civil suit had been tossed, so that they couldn’t be made to turn over additional evidence that could aid the family’s case.

He’s said that ‘they knew that a civil lawsuit could not proceed unless we knew who signed the transfer order, who directed and who approved putting him in a place where everybody knew he would be murdered’, finally adding that ‘they just don’t want this information to go to the public. And they don’t want to prosecute their own, and they never will.’

A spokesperson for the U.S. Attorney’s Office in the Northern District of Virginia rejected Brennan’s claims, stating that ‘the civil case brought by Bulger’s family had no impact upon the criminal investigation or the timing of the indictment’. 

One very interesting, and equally as perplexing detail remains, however. According to an intake screening form that Bulger filled out, when it came to the question of whether there were any reasons he should be kept out of general population, he answered ‘no’. 

No one knew better than Bulger that he was marked for death. Was he under the (evidently false) impression that he would be provided some kind of protection? Was it just his flawed perception, or was there something we don’t know about? Was he just losing it by this point, dementia/Alzheimer’s or just cognitive decline, unaware of what he was signing? Or was this – still – part of the act, the same act that made him deny his entire life that he was ever a rat, his health gone, his freedom gone, his legs gone, but his pride still strong as ever? Or perhaps merely indifference, or even acceptance, towards death from this sick, wheelchair-bound, universally despised by the criminal world he dedicated his life to, the only world he ever knew, back-to-back lifer 89 year old?

Coleman’s former warden has said that he thought Bulger ‘wanted to die’, adding how he believed that ‘whatever issues he had, he had come to peace with them.’ The warden’s view seems to go back to the incident of Bulger’s chest pains while examined, and the nurse’s suggestion that he go see a heart doctor. Bulger didn’t just refuse, he threatened her, telling her ‘I know people. I still have connections back home’ – and that’s what set in motion his doomed transfer to Hazelton. 

Epilogue

A meager and lacking funeral was held, with just family members (including his brother and former Massachusetts state Senate president William) and the twin sister of Catherine Greig attending, but outside that small gathering, there came about one of the greatest, grandest processions of attendants – just not in mourning.

Steven Davis, whose sister Debra was reportedly killed by Bulger in 1981, stated that he ‘died the way I hoped he always was going to die.’ 

‘It’s just sad that it took so long’, said Carmen Ortiz, the former US Attorney for Massachusetts who oversaw Bulger’s prosecution.

Tommy Donahue, whose father Michael was shot dead by Bulger in 1982 in a hail of bullets intended for someone else, said that if he could, he would ‘put money in the guy’s canteen, whoever killed him’, and that ‘it’s going to bring me a lot of pleasure knowing that for eternity he’s going to get a pitchfork in the ass from the devil himself.’ 

Another former US Attorney for Massachusetts, Rachael Rollins, was quoted saying that ‘in the truest of ironies, Bulger's family has experienced the excruciating pain and trauma their relative inflicted on far too many.’

Though perhaps no statement in reaction to Bulger’s death managed to sum up the overall sentiment than another former US Attorney for Massachusetts,  :

‘We received word this morning about the death of James “Whitey” Bulger. Our thoughts are with his victims and their families.’

Kicking a dead horse when it’s fully deserved.