Transcript: 205. The Disappearance of Hitman Chris Flannery, aka Mr Rent-a-Kill | Australia

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On the morning of Thursday 9^th May 1985, thirty-six-year-old Chris Flannery left his apartment building in the heart of Sydney’s CBD, to meet his boss – and was never seen or heard from again.

When his wife Kathleen reported him missing that night, it came as little surprise to police. Chris was no stranger to authorities, as he had been causing trouble in Melbourne, Perth, and Sydney for more than a decade. Rumoured to be a hitman, who went by the name Mr. Rent-a-Kill, the general assumption was that the tables had turned and that, this time, Chris’ number was up. The fact that he was on his way to meet prominent Sydney crime figure, George Freeman certainly did not bode well.

His story was portrayed in Season 2 of the popular Australian crime drama ‘Underbelly’ and many documentaries investigated the life and times of the fierce man with the imposing stature. Still, to this day, no trace of Chris Flannery has ever been found.

>>Intro Music

Christopher Dale Flannery was born into the working-class community of Brunswick, Melbourne, Australia in 1948 to Edward William and Noelle Mary Flannery. He had two siblings: a brother Edward and a sister, Erin.

His father, who was reported to be an abusive and chronic alcoholic, left the family home when Chris was only 9 years old. Young Chris had a turbulent home life and attended a stream of schools. From a young age, he dabbled in petty crimes.

Because of his increasing criminal behaviour, Chris was sent to the ‘Morning Star’ Juvenile Boys Home in Mornington when he was 14 years old. Morning Star was established in 1932 and run by the Franciscan Monks as an educational and correctional facility until it was closed down in 1975.

Members of the ‘Care Leavers Australian Network,’ gave evidence to an inquiry held in 2012 and Leonie Sheedy presented the findings that the boys of Morning Star had absconded the facility to escape the torment that they suffered at the hands of their abusers. A further inquiry found that widespread abuse had been inflicted by the monks on the boys in residence throughout the years. Christopher Flannery was one of those boys.

By the time the Victorian Parliament had concluded their investigation into the abuse of children in the various institutions they had acquired 50,000 witness statements and approximately 10,000 of them related to the ‘Morning Star Boy’s Home’.

Flannery didn’t often speak of his time at Morning Star, but it had a profound effect on him. He was incarcerated at HMP Pentridge with Ray Mooney, who alluded to the terror he suffered as a teen. Ray recalled a conversation which he had with Flannery:

“To try and eliminate the floggings that these friars would give him he tattooed a [boob] tattoo of a crucifix across his back. Shoulder to shoulder, neck to arse. Horrific, this incredible [boob] tattoo of a crucifix. And of course the first time I saw it was when we were in prison. I said ‘mate, what in the hell did you get that for?’ He said, ‘Ah Ray,’ he said… He said, ‘you wouldn’t believe how bad they were. I was terrified of them; I’m not scared to admit it. So, I thought if I got this crucifix tattooed across my back they’d would stop flogging me.’  I said, ‘that’s pretty smart mate. What happened?’ He said, ‘when they saw it, they gave me the thrashing of my life.’”

The violence inflicted by the monks became part of Flannery’s daily life while at Morning Star. With the monks meticulous and organized abuse becoming ever more frequent in their attempts at breaking Flannery’s defiant persona. Indeed it was common practice to use the older boys to punish the younger ones, in their twisted attempts at making the juveniles submit to the chain of hierarchy at the Morning Star Boy’s Home. Even when Flannery was offered the position of one of the monks’ whipmasters, he refused to turn on his friends.

Spending his teens in such an abusive, vicious and loveless environment made Flannery grow into a hard, aggressive and sometimes bitter young man. He defied authority every chance he got – and he hated people in positions of power. It was perhaps no surprise, that at the age of 19 he had a rap sheet as long as his arm: housebreaking, robbery, car theft… He was eventually sent to Pentridge Prison for a number of violent offences, including assault and rape.

Pentridge closed its doors in 1997, and an article in The Age describes it as follows:

“It was bleak. A place of rape, drugs, despair and overwhelming hopelessness.”

In true style, Chris Flannery refused to submit to the prison rules and was transferred to the infamous ‘H – Cell,’ otherwise known as Hell among the inmates. This is where sadistic violence was inflicted on the prisoners by the guards. They were ridiculed, beaten-up and subjected to hard labour.

Sadly, Flannery was no stranger to this kind of abuse and as would be expected he would not bend to the will of the guards and their rules. Beaten but not broken Flannery stripped naked and went on a hunger strike, bringing media attention to the conditions within the prison and the violence inflicted by the guards.

The years of abuse that was meted out on Christopher Dale Flannery, formed and moulded the man he would become. A system that should have protected him as a child and protected his basic human rights as an adult, had failed. Instead of the rehabilitation promised, Australia’s correctional system gave birth to a monster, it created one of the country’s most notorious hitmen.

24-year-old Flannery was released in 1972 (four years early), having known nothing but desertion by his father, abuse by those who claimed to stand for God’s will and compassion, violence from those who claimed to uphold the law. For the first time in his life, he was free to find his way in the world, to do things his way.

And his way, was more often than not, the violent, criminal way. Soon after he was released Flannery got arrested again, this time for armed robbery. The court was lenient and granted him bail, which would prove to be a grave mistake. Flannery went on the run and made his way from Melbourne to Perth where he hoped for a new start in life. Indications were that he tried to turn over a new leaf when he managed to secure an honest paying job at the men’s department in the upscale David Jones store.

People who knew Flannery, thought that the job suited him well. He had a keen eye for fashion and as a tall, handsome man himself, always took care to look his best. However, his attempt at making an honest living was short lived, as not long after arriving in Perth, together with two accomplices he robbed the store where he worked at gun point. He was eventually caught in Sydney in 1974. Though he was never convicted of the Perth robbery, he was sent back to Victoria and jailed for a rape that he had previously committed in Melbourne and found himself in prison for another three years.

After being released this time, Flannery’s journey would take a more sinister turn and his life would now forever become linked with the Australian organised criminal underworld. He formed a connection with a rising star within the gangster world by the name of Alphonse John Gangitano.

Unlike Flannery, Alphonse grew up in a wealthy family and attended the private schools of De La Salle College and Marcellin College, by all accounts he does not have appeared to have struggled for anything financially. Alphonse’s teenage years were spent dreaming of becoming a high-profile gangster in Australia and it was that fascination with the old gangster movies that wetted and fed his appetite an attitude that led him to having a lack of respect for ordinary people’s property, in short if he wanted it, he would take it. He would go on to be a big player in Melbourne’s underworld as part of the famous Carlton Crew. When he started out though, his strategy was simple: to build his reputation within the Melbourne criminal underbelly he began targeting off-duty police officers with his small-time gang, by catching officers unawares while they were enjoying a night out.

And this is how Flannery’s and Gangitano’s paths crossed…

After being released from prison in 1977, Flannery went to work as a bouncer at a well-known night club and massage parlour in the St Kilda area of Melbourne, Mickey’s Disco. In the seventies, this establishment was a favourite hangout for local gangsters. Flannery quickly became bored with his new ‘bottom of the food chain’ employment status. And even though most of his adult life was spent as a career criminal, he had not been very successful in that line of work either, as he always got caught.

But he decided it was time to take charge of his own luck. Flannery allegedly told his friend, Alan Williams:

“I’m no good at this, this crime thing. I think what I’m going to do is kill people for a living.”

And thus, the small-time criminal became the proud owner of his first business, a hitman for hire, ‘Rent-a-Kill Incorporate,’ and quite regularly boasted of his new vocation to his criminal friends.

You see, Flannery believed that murder was the easiest crime to get away with and for $50,000 Australian dollars, he would kill anyone he was asked to kill. And then came his first contract…

Roger Wilson was a barrister in Melbourne and had gotten himself mixed up with some rather unsavoury characters and dabbled in deals with the wrong people. When they didn’t get a return on their investments, they put a contract out on Roger and Flannery was only too happy to oblige.

A detective with the Melbourne police, Brian Murphy, got news that Roger’s life was in danger and there was a contract out on him. Murphy was a good cop that was prepared to break the rules to put the right people behind bars and no one was off limits. Although his methods were somewhat unorthodox, he was determined when he set out to catch his man that he would get him. As a detective, Brian ‘The Skull’ Murphy, simply refused to follow the rulebook.

When Murphy got wind of the contract out on Wilson, he immediately rang the Melbourne homicide division. Here is his own account:

“I rang homicide and they said, ‘well have you got a body?’ I said no, you got to be fucking joking. He said, ‘no I’m not actually. When you get a body, you ring us.’ So we told them to get fucked and went on our way.”

It has been alleged, that on the afternoon of Friday the 1^st of February 1980, Roger Wilson was behind the wheel of his Porsche, heading home to his wife and three daughters at St Clements Jersey Studd, Gippsland. Aa he was coming up along the South Eastern Freeway, near inner city Richmond, he was pulled over by two detectives in an unmarked police car. Well, men posing as detectives, pretending to drive an unmarked vehicle. They were in fact none other than Chris Flannery and his associate, Kevin ‘Weary’ Williams.

Flannery and Williams handcuffed the lawyer and bundled him into the back seat of their car, driving off and leaving the Porsche on the roadside. At a quiet spot near Pakenham, they dragged Wilson from the car, following which Flannery shot him in the head, but the bullet merely glanced Wilson. Wilson ran for his life, into the bushland. Flannery annoyed with himself because of this blunder, went into a rage emptying his gun into Wilson’s back and head.

Flannery and Williams then proceeded to bury Wilson’s body in a shallow grave, not far from the spot where he had received his fatal gunshot wounds. With the body concealed, the men then went back to the Porsche, drove it to Tullamarine and left it in the airport car park, suggesting that Wilson had done a runner if the police came upon his car. When Wilson didn’t return home, his wife alerted police.

Flannery eventually went on the Mike Willesee show to talk about crime, but this wasn’t a very smart move, as Wilson’s farm manager Terrance Crompton recognized Flannery as the man who had been snooping around the farm prior to Wilson’s disappearance.

In August 1980, police believe they had sufficient evidence to arrest Flannery, considering their star witness was Kevin Williams’ girlfriend Deborah Boundy, who had overheard Flannery and her boyfriend speaking about how Wilson had been killed in great detail.

In the days leading up to the arrests, Flannery became increasingly concerned that the police would find their victim’s body. So Flannery persuaded two of his associates from Mickey’s disco to exhume Wilson and relocate the remains. One of those associates was 22-year-old Alphonse Gangitano. Gangitano often told his gang that digging up Wilson’s body was one of the worst things he had ever had to do.

Melbourne Media got wind that Flannery was a gun for hire and had in fact been the person that had murdered Wilson, so they confronted Flannery, asking:  

“You are obviously very much aware of rumours which linked you with certain incidents in Melbourne, several months ago.”

Flannery nodded and said yes. The interview continued:

“It was being rumoured that you had been retained as a hitman.”

…to which Flannery responded:

“That’s incredible, just rubbish.”

Then…

“You have heard this though… And what’s your answer to that?”

Flannery answered:

           “It’s just ridiculous. Totally untrue.”

Flannery had a problem, with Deborah Boundy willing to testify for the prosecution as to what she had overheard, she needed to be stopped and the eager, budding criminal, Gangitano was only too happy to step up once more. He supplied Deborah with pure heroin, which she injected herself with, dying soon after. No witness, no case...

In October 1981, Flannery was free and Gangitano’s reputation was on the rise. However, as Flannery left the court building, detectives from New South Wales Police immediately arrested him for the murder of Sydney brothel owner, Raymond Francis ‘Lizard’ Locksley whom had been killed at Menai on the 11^th of May 1979. The subsequent trial in 1982 failed to reach and verdict, and in a retrial in April 1984 Flannery was acquitted of Locksley’s death.

After his acquittal, Flannery purchased a house in Arncliffe, Sydney and settled in a new city with his wife Kathleen and their two children. Kathleen and Flannery had known each other for a long time and stayed in contact while he was in prison. When he was released, they met up and that was it – nothing could ever keep them apart again.

Flannery was feared by all who knew him. At first sight, he looked like a gentleman, nothing about his appearance indicated that he was a ruthless killer. But once people got to know him, they soon learnt about his explosive temper. After a couple of drinks, fights often occurred, and no one wanted to be anywhere near Flannery. When he blew his fuse, the well-dressed hitman would turn into an unpredictable streetfighter with fists of steel.

It was said however, that the only person he was afraid of, was his wife. Kath seemed to have a strong influence over her husband. Everyone who knew them said that theirs was a Romeo/Juliet-style, all-consuming love – that they would do anything for one another. Kathleen provided Chris with a homelife, support and structure he never had before. And many speculate that if it wasn’t for her, Chris would have continued his cycle of committing crimes, being arrested and spending time behind bars. He was hot-headed and when he snapped, there was no telling how far he would go. However, knowing he had his wife waiting at home kept him in check somehow. An acquaintance of Flannery’s, Craig Cousin, claimed that Chris always knew when to call it a night, saying that his wife ‘would have his nuts’ if he stayed out too late. And everyone believed that she would have.

Eager to get back to work, Flannery formed a connection with Sydney crime boss, George Freeman. However, Mr. Rent-a-Kill was still open for business and it wasn’t long before another contract came Flannery’s way. Terrence Basham had been part of a drug ring with importers Bruce Snapper Cornwell and Barry Bull. Basham had fallen out with Bull and Cornwell over profits from the drug ring, resulting in Basham assaulting Bull. In retaliation, Bull and Cornwell had paid Flannery 50,000 dollars to take care of Basham.

Terrance, his partner, Susan Smith, and their two-year-old daughter lived on a farm in Murwillumbah [Murr-WILLum-bah], NSW far north coast. On Friday the 13^th of August 1982 tragedy struck when Terrence and Susan were shot dead inside their farmhouse.

Flannery entered the home of the couple through the back door of the property shooting Terrence first, but not killing him. When Susan rushed in to check on Terrence, she was shot in the head, killing her instantly. The hitman then turned back to Terrence and this time shot him in the head, finishing the job. One of Flannery’s most heinous acts of his criminal career followed. He left the couple’s 2-year-old daughter with her deceased parents. The little girl was found clinging to her parents lifeless and bloodied bodies when their murders were discovered the following day. In Flannery’s mind, killing Terrence and Susan was business. The fact that he had taken an innocent child’s parents away from her, and even worse, left her with their corpses to fend for herself, did not affect him in the least.

Sydney crime boss George Freeman knew he had to try and get Flannery under control. However, Flannery did not respond to orders and nothing could stop him from going on his rampages. And things were threatening to spiral out of control…

In late 1984, Flannery became involved with the Sydney gang wars. It was a tumultuous time in Australia’s harbour city with gangs marking their territory. Drug turf conflicts and heavy drinking caused many, violent pub brawls, one during which Neddy Smith bit a chunk of flesh from a man’s face in a bar in Surry Hills. Smith and his cronies also came in conflict with Barry McCann’s crew and after punching out McCann’s son in McCann’s pub, he lined up the bouncers, made them face a wall and beat each of them with a baseball bat until they collapsed. After this incident, Smith and two of his men were met with a hail of bullets when they left a pub in Pyrmont one night. One man was seriously injured, but no one died.

Crime and violence were rife on Sydney’s streets. Gangs were everywhere and cops were corrupt. This, in Flannery’s mind, was the perfect environment for him, and he decided to pledge his loyalty to Neddy Smith and his gang. However, Smith claimed that as time went on, Flannery became increasingly paranoid and he was…

“…running around shooting at anyone he thought had anything to do with Barry McCann or Tom Domican.”

Smith also claimed that police attempted to negotiate an end to the gang wars but there was no stopping Flannery. On the 6^th of June 1984, he attempted to execute Sydney Drug Squad detective, Mick Drury. Drury had been the undercover agent involved in drug operations that had resulted in charges against Flannery’s friend Alan Williams.

Williams later stated that Flannery had tried to bribe Drury through bent detective, Roger Rogerson in order to get the charges dropped. However, as Drury had refused the bribe Williams says he agreed to pay Flannery and Rogerson $50,000 each to murder Drury.

As Drury stood at his kitchen sink during the evening, shortly after 6pm on the 6^th of June, two shots were fired through the window. Drury was hit, but fortunately survived.

Before his death many years later, Drury described Flannery in an interview:

“In many ways he was a true sociopath. He had very little regard for the well-being of other people. And this is quite a disturbing psychological trait to have. He would often brag amongst other people of the crimes he’d been involved in over the years. I think a lot of people in Sydney, in the organized crime world, realised also that Chris being the homicidal maniac that he was could not be trusted by anyone. He had no loyalty to any individual or crime group… Chris Flannery was the person that shot me at my house that evening.”

Flannery had crossed the line, shooting a police officer at home with his family in the next room. This reckless job became the event that initiated his downfall. Both the crime bosses and the police knew something had to be done.

On the 27^th of January 1985, as Flannery and Kathleen walked to towards their Arncliffe home more than 30 rounds were fired from a passing car. Although no one was seriously injured, Flannery suffered a bullet wound to his hand and some minor abrasions. Flannery blamed Tom Domican who was charged and convicted of attempted murder, but it was later overturned on appeal.

In the days following the shooting, crooked cop, Roger Rogerson was also seen near Flannery’s house. He was pulled in for an interview but stated that he was just curious to see what sort of damage the gun had done however, he was released without charge. Detective Drury was also pulled in for questioning, as they could not exclude the possibility that he had gone rogue, but he was never seriously considered a suspect.

Flannery had become a liability to the crime world of Sydney, but he threatened that if he went down for the attempted murder of Detective Drury then he was going to spill the beans and tell police everything he knew, about everyone.

The much feared and out of control Mr. Rent-a-Kill realised that he had a target on his back and turned to drugs to stay alert. However, this only provoked his aggression, which was always simmering beneath the surface.

On the 23^rd of April 1985, Flannery carried out the execution of one Tony Eustace allegedly under the orders of his employer George Freeman. It is believed Flannery shot Eustace six times and Eustace was later rushed to hospital, where he succumbed to his injuries. Police were able to question Tony before he died but he refused to tell them who had shot him.

After the attempt on his life and obviously concerned for his family’s safety, Flannery rented an apartment at the Connaught building, which was located on Liverpool Street, near the Sydney Criminal Investigation Branch.

But were they safe? Perhaps not. On Thursday the 9^th of May 1985, Neddy Smith saw Chris Flannery exiting the Connaught apartment complex, and get into the back passenger seat of a car being driven by two Sydney police detectives with whom Flannery was friendly.

On the car stopping at a set of traffic lights near The Connaught on Liverpool Street, Smith observed another two police officers quickly jump into the back seat of the vehicle sitting on either side of Flannery. That was the last time anyone ever saw Flannery.

An investigation into the disappearance of Flannery commenced. Not a great amount of evidence came to light, but the investigators concluded that Flannery received a phone call George Freeman just before 8am on the morning of his disappearance. During the phone call Mr. Freeman is believed to have requested that Flannery come to meet him at his home residence.

On entering the carpark, Flannery discovered that his new car would not start, so he quickly returned to his apartment to inform Freeman of his problem, upon which he was instructed to catch a taxi instead.

But when he went out to the street, he saw a car waiting, and accepted a lift. Who then were the people seen by Neddy Smith, driving Flannery away? To this day, no sign or trace of Christopher Dale Flannery’s has never been found.

However, although police could never prove it, it is widely believed that Freeman ordered his death. Brian Harding, Detective Superintendent stated that:

“George Freeman was a very cunning man. Flannery was still employed as his minder/bodyguard. Flannery and Freeman used to regularly take a sauna together. On one of those occasions…Freeman casually mentioned to Flannery that he had access to a high-powered machine pistol. And in fact said to Flannery ‘are you interested?’ Ultimately what we’ve been told that during the course of the conversation, there were two other people at the house, and Freeman went and retrieved the machine pistol. So Flannery fully expected the machine pistol to presented to him in his presence, but what he did not expect was to be shot with the same firearm.”

Both Rogerson and Freeman denied having anything to do with Flannery’s murder, yet both had very clear reasons for wanting him dead. And considering the revelations that have unfolded over the years it is not beyond belief that both had too much to lose if Flannery talked and turned police informer, which is why the two hardened criminals may have joined ranks on this occasion.

In 2018 Detective Drury, gave an interview to 60 Minutes Australia during which journalist Nick Greenway asked if Chris Flannery was the one who had shot him back in 1984. Drury confirmed that he believed it was the notorious hitman who had shot him. As to Roger Rogerson’s involvement, he commented:

“He actually drove the motor car that night. I have no reservations about that whatsoever. And it makes logical sense that to go in and do a job like that you needed someone who could protect you so that you wouldn’t be stopped by the police. And the perfect driver would have been Roger Rogerson.”

In light of the evidence, we can perhaps conclude that around 8am on the morning of Thursday 9^th of May 1985, following a telephone call received from George Freeman, Flannery attempted to make his way to Freeman’s place of residence. The car had already been tampered with by person/persons unknown and Roger Rogerson waited as previously planned with Freeman for the opportunity to pick Flannery up in his unmarked police car.

Rogerson, together with a least one other officer drove Flannery to Freeman’s Yowie Bay residence where Flannery was shot, and his body disposed of in an unknown location. Speculation varies. Perhaps he was dumped out at sea, another theory goes that his body was mulched and his remains scattered across the city, while there are some who believe his body was laid to rest in a concrete foundation somewhere in Sydney. In 2012 skeletal remains of three victims were discovered in the dunes at Kurnell, not far from Yowie Bay. However, DNA testing proved that none of the remains were Flannery’s.

In February 2004, Rogerson spoke frankly about his theory regarding Chris Flannery’s disappearance on Australian TV:

“Flannery was a complete pest. The guys up here in Sydney tried to settle him down. They tried to look after him as best they could, but he was, I believe, out of control. Maybe it was the Melbourne instinct coming out of him. He didn’t want to do as he was told, he was out of control, and having overstepped that line, well, I suppose they said he had to go but I can assure you I had nothing to do with it.”

Flannery had become a liability to criminals in organised crime circles in Sydney. Because he threatened to inform police about their operations, they no longer trusted him. He was a loose cannon that had to be retired.

It is unlikely that Flannery disappeared of his own accord. People who knew him doubt that he would have been able to remain unseen for so long. Flannery, always charismatic, visible and who likes to be in control would struggle to exist under the radar, even if it was to save his own life.

His wife Kathleen believes he was murdered and spoke openly to the media about her suspicions. She had no illusions about her husband’s chosen career, and knew he was no angel. An understatement of course, seeing as he is considered to have killed about 12 people. But after being fired at herself, all the way to their home where their child opened the door, she knew that Chris was no longer alive. She claimed that in the days that followed his disappearance, Roger Rogerson offered her $50,000 on behalf of George Freeman, to atone for the loss of her husband. A sneer perhaps, that this was the amount Chris usually charged for a hit. To Kathleen, this offer was as strong as an admission of guilt, which means regardless of what they did with her husband’s remains, to her, Chris’ murder is no mystery at all…

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