Comanchero Alex Bourne was jailed for more than eight years on Tuesday while his "apprentice" was allowed to walk free from court, the judge showing the younger man a fork in the road.
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Bourne, 30, was teaching 19-year-old Connor Manns the "trade" of intimidation and violence when they committed the blackmail crime for which they were both to be sentenced.
But while Manns' youth worked in his favour, prosecutors argued Bourne's expressed intention to keep his membership with the bikie gang called for a tougher sentence.
In December 2016, Bourne had accused a man of dealing drugs in Comanchero "territory", before he and Manns threatened the drug dealer and took his money.
Bourne was later caught trafficking drugs when he handed MDMA to the dealer.
In a separate incident, Bourne had ordered another drug dealer, who purportedly lost an ounce of his drug ice to a thief, to place his hand on concrete. Bourne smashed the man's hand with a sledgehammer.
Manns had earlier pleaded guilty to blackmail.
Bourne too had pleaded guilty to blackmail, as well as inflicting grievous bodily harm, drug trafficking and receiving stolen property, which related to a $5000 motorcycle.
Justice Michael Elkaim first addressed Manns, who he called an apprentice in "the awful trade of intimidation, violence and drug use".
He said Manns, who was never a patched member of the club, had the advantage of being in court on Tuesday next to Bourne to hear the significant sentences to be imposed on him.
He said Manns faced a fork in the road.
One road led to rehabilitation and lawfulness.
"Alternatively, he could complete his apprenticeship and look forward to many years in which his unlawful career will be interspersed with significant time in prison, where he will be deprived of his liberty, his ability to be with his family and his capacity to lead a decent life."
Justice Elkaim then turned to Bourne.
The court heard that Bourne, who has the motorcycle gang signifier "1%" tattooed on his neck, had no intention of leaving the club.
Prosecutors had earlier argued that Bourne's continued association with motorcycle gangs called for a tougher penalty at sentence.
Defence barrister James Stewart said while Bourne had been honest about his intentions to stay with the Comanchero he did not want to be involved in this kind of behaviour again. "You can still be a member of the club and not be a criminal," Mr Stewart said.
But prosecutor Anthony Williamson said the risk of Bourne returning to crime was high so long as he remained committed to the lifestyle and culture associated with bikie gangs.
Justice Elkaim said the court had already warned the bikie about the connections between the club and his criminal offending.
"It is unfortunate that he has continued to be part of an Outlaw Motor Cycle Gang, membership of which almost demands involvement in illegal activities."
The judge said that when a "club is apparently more interested in carrying out criminal conduct than lawful and legitimate activities, membership of it is to be discouraged."
He said the courts can and must send a message to both the community and anyone who might be contemplating membership of an outlaw motorcycle gang.
"They must be made aware that their descent into criminal behaviour will be swift and, when apprehended, their punishment will be severe."
Justice Elkaim jailed Bourne for 8 years and 8 months, setting a non-parole period of 6 years and 3 months.
Bourne will be eligible for release March 2023.
Manns was sentenced to 18 months imprisonment, but after already serving nearly 11 months in custody he was released on a good behaviour order for 18 months.
The judge ordered Manns to complete 50 hours of community service, and also banned him from associating with any Comanchero.
