Australia’s Most Notorious Hit Men

This article is supported by Sicario: Day of the Soldado, in cinemas June 28. In the film, the drug war escalates as Mexican cartels smuggle terrorists across the US border. Dealing with themes of crime, killings, and gangs, in this piece we explore infamous Australian hitmen.

For my 16th birthday my cousin swooped me up in a hotted VL Turbo and demanded I wear a collared shirt because he was taking me down Chapel Street. We drank Coronas in the multi-level car park behind KFC and peered out into the long line of fluoro-clad girls outside Viper Nightclub.

My cousins ushered me passed the two speed-riddled bouncers and upstairs. DJ Kat was pumping trance and all the men were wrapped in leather jackets beside private booths. My cousin pointed to a young guy who had the front of his hair gelled upwards. “That’s the most dangerous man in this room, you know?,” he said. All I knew was that he was certainly the smallest. “He was Benji’s best mate; that bloke's a hit man.”

To put out a human life in Australia will cost roughly $16,500, according to a report by the Australian Institute of Criminology, but prices can fluctuate from as little as $500 to more than $200,000. The AIC report claims that the most common motives for hiring a hitman are revenge, drug debts, financial gains, and the silencing of witnesses.

Some of Australia’s contract killers became infamous after the Underbelly television series revived their disfigured narratives. We track the history of three notorious Australian hitman, to illustrate the nature of guys who operate in death.

Andrew “Benji” Veniamin spiralled into infamy as the tattooed villain in Underbelly. Raised in Sunshine, he made a name for himself as an amateur boxer who made the state team. Legendary Olympic boxing coach Beau Gerring described Benji as a “whippersnapper” and only discovered the young fighter's extra curricular activities when police showed up to his gym in the early '90s. Benji got busted for an armed burglary of a cigarette truck, in which he held a salesman hostage. After being convicted—they found all the cigarettes under his bed—Benji served three years in the notorious Turana detention centre for young offenders and graduated back to the streets by stealing cars and pushing drugs.

Benji founded The Sunshine Boys streetgang with Dino Dibra and Paul Kallipolitis. He would later be named by the Purana Task Force as the main suspect in both of their murders. Benji’s lawyer, Tony Isaacs, recounts asking him how things were going in his life. “Oh, things are going great, I’ve got a new job where I wear gloves,” Benji replied. Police believe he started his rampage after he shot dead his old boss, fruiterer Frank Benvenuto, in his car in May 2000.

At the age of 26, Benji rapidly climbed the ranks of the underworld and was hired as a bodyguard for drug barron Carl Williams who, at the time, was at war with Mick Gatto’s infamous Carlton crew. Benji was nicknamed Australia’s busiest hitman by Gatto, who claimed he had killed at least six men.

According to police intelligence, after Benji had murdered Benvenuto, he killed Dino Dibra five months later followed by the murder of Nik “The Russian” Radev who was killed in Coburg on April 15, 2003 and the murder of Paul Kallipolitis, whose body was found in October 2003. And that was before what long-time friend and getaway driver Faruk Orman has described as Benji’s 'crazy time'. The gangland wars would claim roughly 30 murders in the space of ten years.

Toward the end of 2003, Williams told his gang members, “I want every one of them dead and every one of their crew dead”. In December 2003, Graham “The Munster” Kinniburgh was gunned down. Gatto was particularly close to “the Munster”, and the word on the street was that Benji pulled the trigger, even though phone records placed Veniamin on the other side of Melbourne.

Gatto began questioning the Carl Williams crew in a series of meetings, one of which was documented by CCTV at Crown Casino. A few months later, Gatto was sitting with Steve “The Turk” Kaya, when Benji strutted in wearing a cap, t-shirt, cargo pants, and thongs. After escorting him to the backroom for a private chat, according to Gatto’s evidence, “I was looking at him in the eyes and his face went all funny and he sort of stepped back and he said, ‘We had to kill fucking Graham… Fuck him and fuck you… he pulled a gun out and that’s when I lunged at him… and I grabbed his arm and the gun went off past my head… I actually thought [the round] hit me'.

“What do you expect me to do?” Gatto asked. “Just stand there and let him do it?”

Gatto said Veniamin was lying on his back “spluttering and coughing blood” when he retreated back to the restaurant with a red, ringing ear. He handed Veniamin’s .38 Smith & Wesson to the restaurant owner, who wrapped it in a paper towel for the police to seize on their arrival. Gatto was acquitted on grounds of self-defense.

Despite being linked to 25 shootings and 15 murders and being regarded by many underworld figures as the most violent hitman Australia has ever produced, Stan Smith was only ever charged for a minor drug offence. Another Sydney enforcer, who ran in the Neddy Smith gang, paused for quite some time before staring me dead in the eye and describing Stan Smith as “extremely dangerous.”

It all began on the docks for Stan Smith, where police regarded him as the toughest knockabout in the area. When he was 18, Smith met Lennie McPherson, an underworld figure widely regarded as the most powerful Australian criminal of the late 20th century, who took Smith under his wing as an apprentice.

The duo would eventually meet up with McPherson's old prison pal George Freeman, and conquer the Sydney underbelly. Freeman ran the books, McPherson was in charge of protection rackets, and Smith was called in whenever someone had to get their hands dirty.

In 1963, another Sydney thug, Robert “Pretty Boy” Walker, shot Smith in an attempt to try and disrupt his gang's grip on the Sydney protection racket. A few months later, McPherson was getting married to his wife Marlene Gilligan when he decided to slip out with Smith, steal a car and pay “Pretty Boy” a visit. They waited for him to leave his house before creeping up beside him on Alison Road in Randwick and opening fire with a machine gun, killing him instantly. They dumped the car and returned to the wedding reception.

There was also the story of Stuart “The Magician” Regan, who earned the nickname because everyone around him disappeared. As a notorious standover man throughout the '60s and '70s, Regan had no regard for the law or the criminal code and often killed at will. His spree came to a standstill when he murdered a two year old boy he was asked to look after, and it was one the leaders of the criminal underworld could not stand for. Regan was lured to one of McPherson's haunts and promised a role in their protection racket, but when he arrived Smith and Freeman brutally executed him because they felt responsible for maintaining the honour of the criminal code.

Smith eventually removed himself from the violence and became a player, dressing in suits and running commercial drug operations. His life took a turn for the worse in 1979 when Smith lost his eldest son to heroin addiction. It’s been rumoured that Smith beat his son's former drug dealer to death before running over him in his car.

By the early 2000s, Smith had silenced his demons and became a man of God. Smith survived the death of his son, his crime partners—McPherson and Freeman—and spent his quiet retirement attending bible study, singing in a men's choir and distributing religious pamphlets. He passed away in his sleep in January 2010.

Christopher Flannery was a notorious hitman who, by the age of 17, had been charged with rape, violent home invasions, assaulting police, and possessing firearms. Flannery was schooled in the infamous “H Division” of Pentridge prison, a high security unit designated for the most violent inmates in Victoria throughout the '80s and early '90s. It’s been alleged that Flannery was repeatedly bashed and sodomised by both the inmates and the guards.

Flannery worked as a bouncer in St Kilda, but found the work boring so he stepped up the underworld ladder by adopting work as a hired gun with the nickname “Rent-A-Kill”. Flannery is rumoured to have murdered as many as 14 people, and police believe his first contract was the barrister Roger Anthony Wilson who was forced off the road, abducted, and taken to a bush in Pakenham where he was shot by Flannery. Police are yet to recover his body.

Flannery was acquitted of Wilson’s murder in October of the same year, but as he left court he was arrested by detectives from New South Wales police for the murder of brothel owner Raymond Francis Locksley, for which he was later acquitted. Upon release, Flannery landed a job working with George Freeman and Neddy Smith, but when the infamous gang wars sparked off, Flannery sided with Smith who claimed in his book Catch And Kill Your Own, “[Flannery] was running around shooting at anyone he thought had anything to do with [Barry McCann] or Tom Dominican.”

During the height of the war, it has been alleged that Flannery attempted to murder Michael Drury, a senior drug squad detective. Before the shooting took place, Neddy Smith claimed in his book that Flannery told a high ranking police officer, “You’re not a protected species, you know—you’re not a fucking koala!”

Underworld sources claim that the attempted murder of Michael Drury would be the most fatal decision of Flannery’s life. In January 1985 when Flannery was returning home from a walk, he was attacked by an unknown gunman who fired 30 rounds from an automatic rifle.

In the book, Line of Fire: The Inside Story of the Controversial Shooting of Undercover Policeman Michael Drury, it was reported that on May 9, 1985, Flannery was ordered to attend a meeting by his old boss, George Freeman. His car wasn’t working so he called Freeman who asked him to take a taxi. Neddy Smith claims that the police were willing to negotiate a deal to end the gang wars but Flannery kept killing people. In his book he claims to have seen Flannery get into a patrol car with police officers. The police alleged they offered to take Flannery to meet with Freeman. Flannery’s body has never been recovered.

This article is supported by Sicario: Day of the Soldado, in cinemas June 28. You can find out more info here.