Stan Smith

Stan Smith - The Enforcer

Stan “The Man” Smith was one of the most feared criminal enforcers in the Sydney underworld for over 30 years and alongside his companions Lenny McPherson and George Freeman practically dominated Sydney’s criminal fraternity from the late 1950’s through to the 1980’s. One of the most successful hit men in Australian history, he was linked to 25 shootings and 15 murders, yet in his life spent only a small amount of time in prison and was also one of the biggest figures in the drug trade. A man who excelled at remaining in the background, his name was so feared that the mere mention of it was enough to bring other criminals into line making him a true Tough Nut.

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Evolution of a Tough Nut

The man who was to become one of the most feared names in the Australian underworld, Stan Smith was a true Balmain boy. Raised in the lower class suburb in Sydney’s west his only destiny was to become a dock worker and a bit of a hard man with no prospects beyond dead end jobs. Born on the 3rd of January 1937, Smith spent time in two of Australia’s toughest reformatory schools Gosford & Tamworth boys, both of which were more like prisons than schools. Leaving school at the age of 13, Smith fell in and out of work on the docks and at the age of 17 was first noticed by the police as a local hard man. At the age of 18 Smith’s life took a turn and he changed his destiny, escaping a life of poverty and dock work. The change was his friendship with local hard man Lennie McPherson, a man who had aspirations to raise his status in the criminal underworld and being 16 years Smiths senior took him on as an apprentice to his protection business. That same year Smith also married his childhood sweetheart Marilyn with whom he remained happily married to until his death. It was these events that shaped Smiths life for years to come and wanting to provide a better life for his family, Smith wandered deeper into the world of crime.

Watching the Red Light

Smith and McPherson joined forces with one of McPherson’s old prison buddies George Freeman and together they formed a triumvirate of Sydney crime, each of them with a role to play in keeping the criminal fraternity under their control. McPherson was the father figure who worked in the area of protection, whereas Freeman ran the illegal gambling and bookmaking side of the empire. Smith was the stick to McPherson and Freeman’s carrot, being brought in when tougher measures were required. His skills were first utilised in the protection of illegal brothels in Sydney where his brutality was in full swing and it was at this time his violence also became a problem for his criminal team mates. Despite being happily married, Smith often engaged in violent sex with women and did not handle rejection well. He was known to inflict a great amount of pain and fear on any woman who refused his advances which often lead to McPherson paying off girls he had injured. His violence to women subsided as time went by with his need being satiated by the other parts of his life with his criminal reputation rising because of it.

Pretty Boy

In 1963 Smith had his first real brush with death as he was shot by rival protection racketeer Robert “Pretty Boy” Walker. Walker had already made an enemy out of McPherson due to being a rival to his protection business and a mouthy one at that, often bragging about being the toughest man in Sydney. After an altercation with Walker over Smith’s beating of a prostitute, Smith decided to teach him a lesson and was instead shot in the chest by Walker’s rifle. It was this action that proved walkers undoing as by almost killing Smith, he had signed his death warrant in McPherson’s eyes.
On the 9th of July, 1963, Lennie McPherson was married to Marlene Carrol Gilligan and it was this event McPherson used to get revenge for his friends injury. Using the alibi of his own wedding, it is believed that between the wedding service and the reception McPherson and Smith (Who was his best man) slipped out and stole a car making their way to Walker’s safe house in Randwick. They waited for him to leave and followed him along Alison Road in Randwick and when they were along side him McPherson allegedly opened fire at him with a machine gun hitting him six times and causing his death instantly. They then dumped the car and clothes used in the attack and retrieved their own car making their way to the wedding reception, the whole incident taking no more that half an hour. The murder stands as a pivotal moment in Sydney’s underworld history as it was the first incident involving the use of a machine gun and also cemented the team’s status in the eyes of the criminal elite. Despite rumours flaring, no charges were ever brought against the two for the murder.

The Magician

Stuart John Regan a.k.a “The Magician” was one of Sydney’s most notorious standover men in the late 1960’s – early 1970’s and apart from being a reckless murderer was also an obstacle to the order within which the team thrived. Smith and company lived by a very simple code, the working class and helpless such as children were off limits. Despite being criminals, they were still family men with their own sense of morality, a morality that Regan did not share. The final straw came when Regan allegedly murdered a two year old boy whom he had been asked to look after. This crime shook the underworld and along with crime lord Frederick ''Paddles'' Anderson the team was said to be responsible for organising his murder. Luring Regan to one of McPherson’s protection rackets with the promise of an entry into their business, Regan was brutally murdered by Smith and Freeman, an action considered by many on both sides of the law to be a public service. Once again no evidence was ever produced to link the team to this murder.

Up In Smoke

The 1970’s was a time of great change for Smith and the team as Smith branched out on his own to enter the world of the drug trade, an action not popular with his friends McPherson and Freeman who were very against getting involved in the world of drugs. Smith became a trafficker of Marijuana, claiming that unlike drugs such as Heroin it wasn’t really harmful and taking advantage of the world the 60’s left behind, Smith saw an opportunity to make big money. By this point in his life he had progressed from being merely McPherson’s protégé and was now not only a full partner but also considered to be the criminal mastermind of the bunch.
Smith moved away from the violence of his past and became the organiser, wearing suits and running his drug operations via telephone very rarely getting his hands dirty. However in 1979 Smith lost his eldest son Stan Jr to a Heroin addiction and whilst it has never been proved, in an act of revenge, Smith allegedly beat and then ran over his son’s former dealer with his car. He was also called before the Royal Commission into Drug Trafficking in which he denounced the drug trade and broke down whilst relating his son’s addiction. However despite these events it was not enough to remove him from Marijuana trafficking and his life as a criminal continued.


Whilst being declared a mysterious disappearance, Christopher Flannery (also known as Rent-A-Kill) was believed to have been murdered by Stan Smith and George Freeman who was Flannery’s employer at the time. Whilst details were never clear and his body was never found, it was believed that Flannery was lured to Freeman’s house sometime in May 1985 with the promise of purchasing a machine pistol off of freeman and insider accounts claim Smith was the trigger man. Flannery was removed due to his freelancing nature, killing anyone if the price was right with little regard for loyalty. It is believed that Freeman saw him as a liability and someone who was too much of a risk to their operation and it was also believed that members of the NSW police force played a part in this disappearance which would not have been uncommon given corruption present at the time and the team’s connections to such corruption.

Lamb of God

In 2003 after a long life of crime Stan “The Man” Smith’s life took yet another turn with him becoming a man of God. A shock to those who knew him, Smith who had been given a devotional book in 1996 by Rex Beaver from the Evangel Bible Church and in 2003 became a born again Christian. It has been presumed that events such as the death of his son to Heroin and both of his associates Lennie McPherson and George Freeman passing away afforded Smith the opportunity to reflect on his life and his mortality. It was not known if his conversion was legitimate, however many insiders believed it was so and until his death in January 2010 he attended Bible study, sung in a men's choir and distributed religious tracts in letter boxes as well as working for several charities giving hand outs in Kings Cross. In his last years Stan Smith may have been a man of God, but in his prime he was a true Tough Nut of Australian crime.

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