Ex-Bandidos enforcer Toby Mitchell believes he is smarter than police and above the law, says a judge who denied him bail.
Mitchell claims two assassination attempts have left him too ill to be kept in prison while waiting to face trial on extortion and assault charges.
But Victorian Supreme Court Justice Betty King said his "contempt" for police means even the strictest bail conditions could not ensure the safety of the man he allegedly threatened at gun point.
"He is from a milieu that don't respect or view the police in the same way as the majority of the community; they have a contempt for the police and the laws they enforce," Judge King said.
She said police monitored Mitchell's calls from prison in which he dismisses his assault on the man.
"I slapped the c*** in the head, that's it," Mitchell said in one call.
"I won't get any time for it, a slap on the street."
Judge King said that in another intercepted call, Mitchell is asked if the police monitor the conversation.
"They will, but I don't say anything wrong, I'm too smart for them," Mitchell said.
Those calls, Justice King said, indicate a disregard for the law.
"The applicant believes, as he states in the (prison) calls, that he is smarter than the authorities, which demonstrates a belief that he can live outside the law," she said.
The connections Mitchell has "made and clearly retained" in his former role as the sergeant-at-arms of the Bandidos posed a risk both to his victim, and civilian witnesses, Judge King said.
Police allege Mitchell, 40, punched a man and demanded $300,000 at a busy South Melbourne cafe in January.
He also allegedly shoved a gun into the stomach of the man - who cannot be named - and threatened to shoot him and his infant daughter.
Defence barrister Christopher Dane QC said his client would plead guilty to assault, but denied brandishing a gun.
Mitchell is facing a string of charges, including extortion with threats to kill, intentionally causing injury and possessing a gun.
He faces a committal mention hearing on the charges on May 6.
Mitchell, in a black and gold tracksuit, smiled at family members in the court as Judge King delivered her ruling.
