The Great Bookie Robbery

July 13, 2020

Great Bookie Robbery; Melbourne, April 21, 1976


“Ray Chuck” Bennett

“Ray Chuck” Bennett was a career criminal (“crim”) in Australia—also known as “The General,” for his ability to plan jobs. He was a well-known bank-robber and smuggler. In the early 1970s, he left Australia and joined the “Kangaroo Crew” in England, pulling heists around the UK when he was arrested. While in prison, he worked closely with a British crew called the Wembley Mob learning military-style techniques for burglary. Using these tactics, he came up with the idea to rob the cash office of the Victoria Club when he returned to Melbourne. This was where all of the legal bookies would gather and tally up bets before the armored truck delivered cash to the Victoria Club. Ray Chuck Bennett decided that the best time to hit the Club would be on cash day. Book-making is a cash business, which would prove to be a double-edged sword.

Ray Chuck (like many criminals in Australia) was a member of the Federated Ship Painters and Dockers Union (“Dockies”). The Painters and Dockers is kind of like the Australian equivalent of the Teamsters or the Laborer’s Union; criminals ran in, all had no-show (“ghost”) jobs, and in 1993, it was deregistered—officially because membership had fallen below 1000. The Painters and Dockers is important because this union (these work conditions) led men to be very close. They trusted each other, and they knew who had which skills. Ray Chuck built his team of fellow criminals who were also union brothers.

The Planning

Ray Chuck Bennett and his team planned the job for months. They rented an office two floors above the target and familiarized themselves with the layout. While there, the men tampered with elevators, causing them to constantly jam between floors, they bypassed the building’s security. They removed the bolts of the fire escape door, cut them in half, glued them, and replaced them, so they could just kick the door open. They even broke into the empty cash office at night and ran practice drills.


For the months leading up, Ray Chuck and his men worked out, getting into shape for the robbery, running and boxing. They quietly, separately gathered weapons so as not to draw too much attention. The team was Ray Bennett, Ian Carroll, Laurie Prendergast, Normie Lee, Vinnie Mikkelson, Brian and Les Kane.

The Robbery

Right off, the armored truck was 15” late because of a flat tire, but the men waited down the street, armed in two vehicles, a panel van, and a large, loud semi with trailer, chosen for the noise. They pulled the van down the alley and the semi in front of the club, the loud engine rumbling. They pulled on balaclavas and kicked the fire door off the hinges. Once inside, they subdued the 118 people in the lobby, used bolt cutters to remove locks, and eventually got away with 118 calico bags full of cash…they were inside for 11 minutes.

The Brilliant Escape

A Melbourne criminal who was known to represent some of the suspected gang members would later tell a couple of different stories of how they escaped. It is said that even he was uncertain which is true. One story is that they all jumped in the van and drove away while an old truck they had parked out front blocked traffic and delayed police access. The second (and more likely based on the attorney’s smirk) is that the men had a safe in their upstairs office. While the people were subdued, rather than running out to the van, they ran up two flights of stairs and hid the money in that safe and it never left the location. They then sped away in an empty van. Whatever the case, the estimated cash take was $8-$15 million. The Victoria Club reported $1.2 million—the bookies vastly under-reported their business for tax purposes, and because most were corrupt, using the money for political pay-offs.

The Aftermath

Each man took half a million to spend immediately and they stored the rest until they could launder it or send it out of the country. Both the criminal world and the police had a good idea who committed the crime, but cops had no evidence, so it fell to the underworld to handle it. They invested in tourist properties throughout the Pacific rim and created trusts.

The Falling Out

The Kane Brothers, Les and Brian, had a long criminal history. They were high-ranking members of the Painters and Dockers, and felt that their standing and connections in the criminal world should entitle them to a larger cut. They began to feud with the tight-knit group of Bennett, Prendergast, and Mikkelson. During a drunken brawl, Mikkelson bit off Brian Kane’s ear. Les Kane, known to be a psychopath, was the biggest threat. He was absolutely going to kill Bennett and his pals. The Painters and Dockers supported the Kanes, and the criminal world became very interested in the $14 million in cash that was just sitting somewhere. On October 19, 1978, Les Kane and his family returned from an outing one night. Suddenly, three men in balaclavas burst into the house, waving guns. They took Les’ wife and children to a bedroom and locked them inside, then shot and killed Les in the bathroom. Les’ wife recognized the men—Bennett, Mikkelson, Prendergast, former friends. The killers loaded Les Kane’s body into the trunk of their car and hauled him away—he was never found. The entire murder closely resembled the Danny Seifert murder in Chicago in 1972 in which Seifert’s widow recognized Joey Lombardo. Kane’s wife abided by the Painters and Dockers “code of silence” when dealing with police. She let his brother Brian handle it.

With Brian Kane and the Painter and Dockers after him, Ray Chuck Bennett knew he was in trouble. He turned himself in to police on minor charges, believing he would be safe in their custody. He was wrong. On November 12, 1979, Bennett was arraigned. While being escorted down the back steps of the courthouse, a man jumped out, fired several shots into him from a snub-nosed .38, and fled. The planning in this hit was impeccable. The officers escorting Bennett were both unarmed, a fence at the back of the building had been dismantled, and the crowd prevented pursuit.

It was later revealed that police had co-operated with Brian Kane, who had committed the murder. The Kane gang was believed to be more predictable, following more rules. The killing of Les Kane in front of his family had soured the police on Bennett and his gang. An unnamed insider even reported that Brian Kane did a practice run earlier in the week, smuggled into the courthouse in the trunk of a police car. The majority of police at the time also believed it was an inside job. Regardless, Ray “Chuck” Bennett was dead.

Brian Kane was shot dead in a pub by two masked men in 1982. Ian Carroll was shot and killed in 1983. Laurie Prendergast disappeared in 1985; his body was never found. Vinnie Mikkelsen fled to the Western States, and stayed there for many years, only returning east after everyone was dead. Norman Lee was eventually charged with the robbery but was acquitted. He was later shot to death by police during a 1992 robbery of a payroll truck.

The moral of the story

The moral of the story is, when you’ve got $16 million in cash in the underworld, things can go south awful damn fast.


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2 comments on “The Great Bookie Robbery

  1. Iain Marshall Jul 14, 2020

    It as a brilliant robbery and 16.Million today would be nice so think about 1976 ,When the Kane’s came calling and the fight broke out and threats to kill Ray Bennett ,Ray should have either done two things ,giving the Kane’s a Million. or Killing Brian Kane. He was a psycho but calm unlike Les who would have been lost without his big brother , In this case it was a problem of getting the millions it was the aftermath and God knows how many stand over men coming looking for you , It had a sad ending most were killed or jailed, Ray Chuck was like the Irish gangster Martin Cahill also known as the general and the Irish Garda (Irish Police) and the IRA, there was another theory another Dublin gangster who was released from jail in 1992 he owed the general but knew he was a dead man walking so why pay the 200 grand when you can take him out. Cahill was a master armed robber, he’d deposit money into a bank then 5 mins later his men would rob the bank so he got double his money, He stole art paintings worth 20 odd million but was difficult to buy ,the final straw was when he allegedly sold some of the paintings to the Ulster Loyalists ,the IRA considered him a collaborator and the IRA wanted a cut before they heard he sold the Loyalists then in late 93 an IRA run pub was attacked by a loyalist gang killing the doorman who was a IRA member, The police were watching Cahill for over 5 yrs 24/7 but could never catch him doing anything ,Then on an August morning the large police presence outside his house had gone, a half hour later while the general was leaving back a video a bike pulled up and the back seat passenger shot the general five times with a Magnum Everyone knew the Irish police were helping the IRA ,

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