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Russell Street bomber Craig Minogue has failed in his bid to one day walk free from jail and must continue with his "de facto death sentence".
The High Court on Wednesday upheld a law introduced by the Victorian government that ensures anyone who murders a police officer has no chance of parole.
Minogue was jailed for life in 1988, with a non-parole period of 28 years, for murdering policewoman Angela Taylor in a car bomb blast on Melbourne's Russell Street. He later killed a man in jail.
The 57-year-old made a parole bid in 2016, prompting Victoria's tough new legislation.
Last year, Minogue successfully challenged the legislation through the High Court, which concluded it did not apply to Minogue because the "offence committed was indiscriminate and no particular person or class of persons was targeted".
Two months later, the government introduced another bill, ensuring Minogue would only be released from prison if he was "in imminent danger of dying or is seriously incapacitated and, as a result, he no longer has the physical ability to do harm to any person".
A second High Court challenge was filed by Minogue's lawyers in April this year, arguing the law was "cruel and unusual punishment".
They argued the Victorian parliament did not have the power to impose punishment through legislation.
But the High Court ruled the legislation did not impose additional or separate punishment on Minogue but simply altered the conditions he needed to meet before being released on parole.